10 timeless wardrobe essentials

10 Timeless Wardrobe Essentials

Text copyright © 2015 Iron & Tweed, Superdrive Publishing Limited

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Published by Superdrive Publishing Limited

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Affiliate Disclosure Some of the links provided in this ebook are affiliate links. If you purchase an item through one of these links, I’ll earn a small commission at no additional cost to you. Thanks for your support!

That said, although I’ve included some commission-generating links, the majority of them are not. These are brands and retailers that I believe in and ones that I’ve purchased from in the past.

I would never link to a junk product for a measly 3% (or even 100%) commission. The happiness of my readers and my integrity are my number one priority.

- Nate IronandTweed.com


Table of ContentsIntroduction............................................................................................1

The Leather Jacket.................................................................................................4

Raw Denim..............................................................................................................7

The Sport Coat......................................................................................................12

The Navy Suit........................................................................................................15

Brown Brogues.....................................................................................................21

Black Formal Shoes.............................................................................................25

The Shawl Neck Cardigan...................................................................................28

Timeless Shades..................................................................................................31

The Classic Timepiece.........................................................................................35

The Quality Bag....................................................................................................40

What to do Now?..................................................................................................43

Conclusion...........................................................................................................45

1


Learning how to dress better can be an exhausting and expensive process. How much should I spend on this? Is this look still in? I saw a cool guy wearing one of these - should I wear one, too?

All are common thoughts when embarking on this journey.

Lucky for you, I’ve made all of the mistakes, read every forum, magazine, and blog post on the subject. I’ve compiled all of the most important information into a guide that’ll help you avoid frustration and some of the more costly mistakes when making some of the bigger purchases.

Why listen to me?

Do I wear a three-piece suit everyday?

No.

Do I dress head to toe in designer labels?

Nope.

Can I be found wearing this seasons hottest trend?

Not a chance.

What I do is dress well everyday. I can pull off a vest, tie, and dress boots at a party, where everyone else is wearing jeans and sneakers, without looking pretentious. My daily attire would be equally appropriate at a dive bar as it would at a downtown steakhouse.

I’ve gone from dressing like an overgrown teenager, lacking a single wedding appropriate outfit, to being generally recognized as one of the best dressed men in most scenarios.

I can teach you how to do the same.

Looking great everyday can only be accomplished by having classic staple pieces that you can rely on. These are the foundation for the rest of your wardrobe.

Introduction

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How to use this book

Each item in this eBook is given its own chapter.

Overkill?

I don’t think so.

As the title suggests, the items I’m recommending are meant to be wardrobe staples that will last for years to come, not some up-to-the-minute fashion nonsense that you’ll regret in three months.

I’ve purposely excluded items like shirts and pants (mostly). They are at the core of any man’s wardrobe but I don’t really consider them to be investment pieces.

I define “investment items” as those pieces that are extremely versatile, get better with wear, and can often be handed down. All of the items in the guide that follows meet at least one of the criteria.

Significant money can and should be spent on these items, since they’ll be your most frequently worn and loved pieces in your wardrobe.

Learn from my mistakes (see: wasted money) and buy the correct pieces the first time around.

Now, I don’t recommend rushing out and buying all ten pieces at once. Rather, read my guide and think about what will work best with your lifestyle.

A 21-year old college student that goes barhopping every weekend will have drastically different wardrobe requirements than a 45-year old bank manager and family man.

The beauty of this guide is that, with only minor tweaks, these items would work for both of the men mentioned above.

This book contains general information relating to the type or style of various wardrobe items, with an overview of construction and materials. This is not intended to be an be-all and end-all guide to clothing.

Discussions on different types of shoe welting techniques have gone on for hundreds of pages - we aren’t going to waste our time wallowing in that kind of detail.

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Instead, it’s my intention to give you the nuts and bolts of each item (maybe a little more) so you have something to refer back to and have enough information to make educated decisions.

Let’s get to work.

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The Leather Jacket

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Why invest in this item

Confidence. Anytime I put on a leather jacket, I feel about 50% more awesome. Leather jackets are the classic symbol of rebellious individuals, and while you don’t have to actually break the law while wearing one, you’ll feel as though they don’t apply to you. Another reason that I consider this an “investment” piece is its ability to get better with age. Don’t try to hasten this process. In time, it’ll become your very own.

Construction

Leather Options

The most common materials you’ll find are calfskin and lambskin. Calf will be a little stiffer, but not by much. On the plus side, it’s more affordable and slightly more durable.

Lambskin is the ultimate in buttery, soft leather. It’s going to be super comfortable right away and as long as you aren’t wearing it to the construction site, durability shouldn’t be an issue.

Features to look for

Leather Quality

A high quality leather product should have a soft glow, rather than a high shine. It should feel soft and supple in the hand and have some variation in color. You should also be able to see the grain if you look closely.

A poor quality leather will look shiny, and a little too uniform in color. This is a result of being sprayed with a thick, tinted coating to mask the low quality surface. Cheap leather will have a distinct “plastic” feel.

Style Options

Bomber - Originally designed for pilots, these jackets have elastic cuffs and waist. The collar can be fur, leather,or fabric. The fit is close to the body and cut short, just below the waist. This is going to be the most versatile style for most men. It’ll have you looking cool without appearing to be trying too hard.

Moto - Similar in fit to the bomber, the moto jacket typically has a small snap band-collar and zipper cuffs. Slightly more edgy than the bomber jacket, but still looks good on most guys.

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Double Rider - Think Elvis, the Ramones, and the Terminator. I wouldn’t recommend this jacket to everyone. Then again, if you have the attitude to pull it off, you won’t need confirmation from me.

Styles NOT recommended - Leather trench coats, blazers, and peacoats. These styles scream the 1990s, depressed teenager, and The Matrix. Not a good look for most.

NOTE: Avoid any styling such as logos, wild colors, over the top stitching, or an abundance of zippers. No synthetic “pleather” either. We’re looking for high quality items here.

Color

Your current (or desired) wardrobe should be most critical when deciding what color jacket to invest in. If you typically wear brown boots and shoes, then opt for a medium to dark brown jacket. If your wardrobe is filled with white, gray, and black, then a black jacket will suit you best.

How to wear

Leather jackets can be extremely versatile, provided you follow the advice above. A bomber or moto jacket in black or dark brown can be worn with anything from jeans and work boots or in place of a blazer in business casual situations.

Where to shop and recommended brands

Nordstrom - Department stores can be a great source for leather jackets, just don’t be fooled by high-end labels. A $2,000 designer jacket probably won’t be any higher quality than a $500 option from a less well-known maker. Use your best judgement and compare the quality, fit, and design to the price.

J.Crew - The regular prices are pretty steep, but keep your eye out for their frequent sales.

Banana Republic - I tried one of these on and it looked fantastic. Would’ve bought it if I didn’t have one already.

Thrift stores - Every time you come across a decent-looking leather jacket in a resale shop, you should try it on. Many vintage pieces are way too short and baggy for most guys, but if you stumble across a gem, you could very well save yourself hundreds.

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Raw Denim


Raw denim should be your go-to casual outfit foundation. They work with just about everything and get better with age. You could wear a single pair five days per week for all types of situations.

Something that versatile, in my opinion, is worth serious consideration.


Raw and Selvedge: Explained

Contrary to popular belief, the denim terms “selvedge” and “raw” aren’t synonymous.

Selvedge denim is produced on old-fashioned shuttle looms and is said to have a tighter, more dense weave than denim that is readily available today. The term selvedge comes from “self edge”, which refers to that little white and red piping you

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Non-SelvedgeSelvedge

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see. That’s the factory finish of the fabric roll as it comes off the shuttle loom.

The term raw (same as rigid) means that the product is in an unwashed state. Most jeans have gone through extensive washing processes before you buy them meaning everyone gets the same generically broken-in pair.

Starting with rigid (raw) is perfect because every crease, fade, and stretch will be unique to your body and lifestyle.

Sanforized vs Un-sanforized

Sanforization is the name for the pre-shrinking process. Levi’s Shrink to Fits, for example, are Un-sanforized (not pre- shrunk) and should be clearly marked as such on the label. As a result, you must size up when buying and shrink them before wearing. Not to worry, most denim is of the pre-shrunk variety you’re used to.

Fabric Weight

• Less than 12 oz = Lightweight - Easy break-in, better for warm weather. Most comfortable, but won’t result in dramatic fades or last as long as mid or heavyweight.

• 12 - 16 oz = Mid-weight - Good all around. Requires some break-in, comfortable in mild temperatures, good fades and longevity.

• Greater than 16 oz = Heavyweight - Stiff, rugged, heavy creasing results in the best fades. Good for cooler weather, denim enthusiasts, and longer life span.

Fit

A good pair of jeans will fit close to the body and conform to your shape. Keep in mind that the idea isn’t to wash these after every wear, so they will stretch a little. No single cut works for every body type, but I can give you a starting point.

Slim guys - Slim or straight cuts will be best (avoid skinny jeans)

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Muscular - Straight cut or relaxed/regular

Heavy guys - Boot cut or regular/relaxed

How to wear

Jeans are extremely versatile, especially in America. Young, hip CEOs of small companies can often be seen “dressed up” in dark denim and a blazer. Everything from t-shirts to button ups and sport coats are at home with a well-chosen pair of jeans.


So, to sum up the features, you should look for: Raw, Sanforized Denim, with little to no embellishment. Whether or not you pay the extra money to move up to Selvedge is up to you.

If at all possible, you should try your jeans on before purchasing. This means department stores, local independent shops, or websites with free shipping and returns.

Nordstrom - Good brands include A.P.C, Naked & Famous, Unbranded, J Brand, Nudie Jeans, Rag and Bone, andLevi’s.

OriJeans - Made to Measure Jeans. If you’re a fan of squats, this is your savior.

Zappos - Try brands like Hudson or Joe’s.

J.Crew - With a wide range of fits, you’re sure to find one that works for you.

H&M - Most of their stuff is too “fashion-y” for me. There are some gems though. The jeans I’m wearing in the photoabove were purchased from H&M for $20 and have lasted me over 4 years. I call that “winning.”

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SuitSupply - Steep price but everything they have is quality. They also have an extremely knowledgable (well dressed) staff that will make sure you walk out of the store with nothing but the perfect items.

Gap - Not a bad price for quality denim, better if you catch a sale.

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The Sport Coat

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Use it to elevate your style when all of your colleagues are wearing khakis and button ups or as an extra layer on a chilly night. It can also take the place of a suit if you’re going for a more nonchalant look.


The distinction between sport coats and suit jackets is more art than science.

There are suit jackets with sport coat characteristics and vice versa. However, there’re several features that set a sport coat apart from a suit jacket that probably won’t be noticeable to most people. The distinction is on a continuum and there really isn’t a clear line between the two.

Sport coats tend to have texture and/or pattern, while suit jackets tend to be solid colored and smooth. Anything with a plaid or windowpane pattern is going to look more like a sport coat. Any fabric that has some texture also point in the sport coat direction.

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Pockets

Suit jackets typically have flap pockets, meaning the actual pocket is hidden between the outer fabric and the liner and the only visible portion is the flap cover. Sport coats tend to have patch pockets. This means that the pocket is sewn to the outside of the coat and the outline is visible, resulting in a more casual appearance.

Fit

A sport coat may be cut slightly roomier than a suit jacket to accommodate a sweater or more “sporty” behavior.

Just make sure it fits in the chest and shoulders and the rest can be altered.

How to wear

Sport coats are worn with odd trousers, chinos and jeans. When pairing with jeans, think in terms of wearing casual sport coats with “dressy” jeans for the most natural looking combination.


SuitSupply - These guys have some serious style and excellent quality. My number one recommendation.

J.Crew - Good quality for the money. Up-to-date and classic all at the same time.

Nordstrom - Any department store is going to have a wide selection. Go find something that fits.

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The Navy Suit

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Every man needs to be able to look his best at a moment’s notice. Have you ever been offered an interview and had to rush out and buy an outfit last minute? I have. And I looked ridiculous due to the poor fit that follows a hasty off-the-rack purchase.

Always have a suit ready to go.

You could get away with just a sport coat and trousers, but I find a complete suit to be the most reliable for the greatest number of occasions. Don’t worry, the high price tag can be offset by frequently wearing the pieces as separates.

A $500 suit worn once per year is mighty expensive. But if worn as separates once per week, it’s a nice way to flesh out a business wardrobe.

And let’s not forget, a man just plain feels his best in a well-fitted suit.


Fabric

I’d recommend that you go with a slightly textured, matte fabric. A smooth/shiny fabric does look classy, but it’s harder to pull off in casual situations. Opting for a more textured fabric will increase versatility by allowing the pieces to be worn more casually as separates.

Just don’t go with anything too bold because it’ll be more difficult to wear frequently. “Look, it’s the guy in the plaid suit...again.”

Lapels

Look for a jacket with notch lapels. They’re more versatile and appropriate for every situation. Peak lapels are more

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formal/fashion forward, but don’t look as natural with jeans and other casual attire.

Vents

This refers to the flaps at the bottom rear of the jacket. A single rear vent is typical of American designers and is usually better for bigger guys. Double vents are more European and look best on slim guys (they may not lay flat on a big behind). You can’t really go wrong with either. Just try both and decide.

Pockets

If you’re going to wear the jacket as a blazer (you should), then you’ll want the more casual patch pockets. Flap (Besom) pockets are more formal and will make the jacket a little more difficult to wear with jeans.

Buttons

Here, your choices are 1, 2, or 3 button design. For your first suit, go with a 2-button design. Single buttons are typically found on dinner jackets or “fashion” brand blazers and should generally be avoided. 3-button jackets look a little too 1990s. They also hide a lot of your shirt and tie.

Construction

A suit jacket is made up of three layers. Working from the exterior inward, you have the suiting material on the outside, a structural mid-layer, and the inner lining. Here, we’re interested in the mid-layer.

Fully Canvassed

In canvassed construction, the mid layer is sewn to the outer layer, allowing for natural movement between the fabric layers. This technique allows the jacket to drape better on the body. Canvassed jackets conform to the body over time, creating a three-dimensional fit and a much sharper appearance than fused construction (explained below).

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Fused

Here, the mid-layer is glued to the outer fabric. This type of adhesion can result in a jacket that appears stiff and lacks natural movement found in canvassed jackets. Another downside is that fused jackets can “bubble”. Meaning that as the glue degrades, parts begin to separate and look like bubbles in the fabric. Many “high end designers” sell this junk at a premium. It’s important to know what you’re paying for.

Half Canvassed

A happy medium. In this case, the chest portion of the jacket is canvassed, providing a great fit in the most important area. It’ll then be fused around the skirt of the jacket. This is a good combination of quality and affordability.

Identifying Construction - Pinch the fabric of the sleeve and take note of the thickness. Now, pinch the fabric on the chest near to the lapel, and compare the thickness. If it feels the same as the sleeve, it is half or fully canvassed. If the chest fabric is thicker, indicating the mid-layer is glued to it, then it’s fused.

Fit

As with most garments, it’s best to go down the middle. About the only thing that changes in terms of suit fashion is the width of various elements. To avoid looking overly trendy and to prolong your investment’s useful life, it’s best to get a suit that fits close to the body without pulling or being uncomfortable.

Shoulders

The shoulders and chest are the most important aspects of jacket’s fit. Nearly everything else can be affordably altered. The jacket’s shoulders should end at the same point as your own. The shape should look natural without any divots (a wrinkle or pucker) forming.

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Pants

Flat front trousers look best on most men. Larger men may look a little better in pleated trousers, but you’ll have to try both styles on to make that decision. Pleated pants look best with a cuff and flat front trousers look good with either. Cuffing your pants adds weight to the leg opening, helping the pants to drape better.

How to wear

The most obvious choice is to wear it as a complete suit for events such as meetings, weddings, and interviews. You can make the suit earn its place in your wardrobe by wearing the pieces separately.

Try wearing the jacket with dark denim for a night on the town or the pants with a nice shirt out to lunch. The point is not to let your suit sit in the back of your closet collecting dust.

Note - If you buy a three piece suit, the vest takes you up to seven possible combinations. Now that’s versatility.


I wish I could give everyone a single source for all of their suiting needs. But, the fact is, every manufacturer has a different fit that will flatter some, but not all. I’ve been dwarfed by one manufacturer’s 42R while being unable to get my arm inside another.

I’ve tried on $2,000+ jackets, at the insistence of salesman, at stores like Nordstrom and Brooks Brothers, and they fit like complete shit.

I’m not talking about just being too big in the waist.

I’m talking about shoulder divots, pulling chest, neck roll, and a bunch of other flaws I can’t even describe. These salesman, working on commission, couldn’t even continue with their pitch. Several of them admitted that they just didn’t have anything for me.

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With that being said, It’s best to try suits on in person. Just know that everything won’t be perfect off the rack and in 90% of cases, some alterations will be required to make it perfect.

SuitSupply - I haven’t found anyone that comes close to these guys for the money. Actually, I haven’t found another brand that could match them at any price point.

J.Crew - The Ludlow and Crosby suits offer two different fits with styling that is both classic and up-to-date.

Nordstrom - Department stores offer a wide variety of brands and frequently have amazing discounts.

Target - If you’re really strapped for cash, a suit can be had for around $100. I wouldn’t consider this a long-term investment, but it’ll get you through a few rounds of interviews.

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Brown Brogues

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It’s the most versatile shoe a man can own. Traditionally viewed as a country shoe, today it’s accepted in all but the most formal business environments. I frequently wear mine with jeans and often with suits.

The term Brogue simply refers to a shoe made of multiple pieces of leather (toe cap, heel cap, and lace panels) with perforation details. The origins are specific to a utilitarian Scottish shoe, but today, it’s used to describe a wide range of styles. Brogues can be wingtip or cap toe, balmoral or blucher, and have a little or a lot of broguing (perforation detail).


As with sport coats, the distinction between “dressy” and “casual” shoes isn’t clearly defined. Rather, it’s the sum of features that causes the style to lean one way or the other. I recommend staying away from either extreme if building a versatile wardrobe is your goal. In the image above, the left shoe is fairly casual while the right is more formal.

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Color

Brown shoes can generally be worn with any color except black. The darker the shade of brown the more formal, orbusiness appropriate. Your best bet is to stick with something in the mid to dark brown range.

Soles

Single leather soles are most formal, double thickness leather soles are in the middle, and rubber soles are more casual. Base this selection on your lifestyle. Choose single leather soles for business and double leather or rubber soles for business casual.

Detailing

The more ornate a shoe’s pattern, the more casual it is. Uninterrupted leather is most formal. Strike a balance by choosing a shoe with a little pattern, but not too much.

Lacing Closure

Balmorals/Oxfords are more formal while Bluchers/Derbys are more casual. If you work in a formal office, go with balmoral. If you’re looking for a versatile everyday shoe, go with the derby.

How to wear

If you choose a pair that cleverly combines both formal and casual elements, brogues can be worn with just about anything excluding either extreme of dress (faded jeans or tuxedoes).


Allen Edmonds - I’ve dropped quite a bit of cash here. They hit the sweet spot between quality and affordability.

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Zappos - Seemingly limitless selection. Free shipping both ways, can’t beat that.

Nordstrom - Great brands and selection. Wait for a big sale.

J.Crew - Check out the Ludlow wingtip. J.Crew has really stepped up their shoe game recently. And they sell Alden if you want the best.

SuitSupply - You’re probably tired of hearing it by now but their style, quality, and affordability is unmatched.

Thrift stores - You can save yourself some serious dough by finding a quality pair of shoes at a thrift store and then using a little elbow grease to bring them back to life.

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Black Formal Shoes

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As with brogues, the goal is to cleverly combine certain details to make the shoes work well with casual wear but also be appropriate for formal events.

When you want to look your absolute best, nothing beats a highly polished pair of black shoes. If purchased intelligently, they will last for years and years and can be worn frequently with jeans and suits.


Balmoral or Blucher Lacing

There’re several factors that influence a shoe’s level of formality, lacing style being one of them. Balmoral (also known as Oxford or closed Lacing) is the most formal, but can look a little out of place with casual clothing.

Bluchers (also know as Derbys or open lacing) are a little less formal, but more versatile. Blucher lacing can be combined with other formal elements like plain toe, black leather, thin sole, and minimal stitching to increase formality.

I like a shoe with a combination such as this because the blucher lacing makes them look good with jeans and all the other elements make them appropriate for all but the most formal events.

Toe Design

As mentioned above, plain toe is the most formal, but cap-toe would also be a great option.

Sole

Leather soles are considered more formal but you could get away with a sleek rubber sole.

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Stitching and Design

The more plain a shoe’s design, the more formal it is. Avoid wingtips and anything with too much perforation detail for this selection.

How to wear

If you go with a combination of formal and casual elements, per my recommendation, then a pair of dark jeans would go great with these shoes, especially in the city.

They’ll also be perfectly matched with odd trousers, suits, or even a tuxedo.

Basically, they’ll be your go-to dress shoe.


Allen Edmonds - Great value for money. This is where I choose to drop most of my shoe budget.

Zappos - Outstanding selection and customer service. Order two different sizes and return one for free.

Nordstrom - Plenty of styles to choose from.

J.Crew - Again, good quality shoes for a decent price.

SuitSupply - Style and customer service, enough said.

Thrift stores - Grab a pair for three bucks and bring em’ back to life with a little conditioner and polish.

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The Shawl Neck Cardigan

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This piece should be considered a hoodie for grown-ups. The versatility, practicality, and comfort are unmatched by anything else in your wardrobe.


Material

Make sure the material is comfortable on the skin. This sounds obvious but I’ve purchased a couple of these sweaters made from heavy wool. My thinking was that they’d be extremely warm and I would just wear them over long sleeves. In reality, they sit in my closet most of the time. The heavy wool is too hot indoors and I can’t just throw it on over a tee because it’s so itchy. Your best bet would be to go with cotton, synthetic, or cashmere.

Weave

A smooth weave is going to be more dressy. Going for something chunky, like cable knit, will give off a more rugged/ nautical, vibe. Just choose according to how you plan on wearing it.

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Pockets

Cardigans often come with hip and/or chest pockets. As you’ve probably guessed, the more pockets on the sweater the more casual it’ll appear.

Fit

Shawl neck cardigans should generally be more form fitting if worn in business environments but can be a little slouchy (if desired) for casual wear.

How to wear

The best part of a shawl neck cardigan is the extreme versatility. Wear it in place of a sport coat, hoodie, or light jacket. You can wear it around the house with your pajamas or out to a nice dinner.

Getting a little chilly on a summer evening? Throw it on with your shorts and boat shoes.

This truly is one of my favorite pieces.


Amazon - Find something you like in a store and get a better deal online.

Nordstrom - Go to your local department store for the largest selection.

J.Crew - I don’t like to think that I’m completely loyal to any brand, but I like most of their offerings.

SuitSupply - They rotate inventory often. If you find something that works for you, go for it.

Target - Despite the low prices, Target does have some worthwhile pieces.

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Timeless Shades

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One of the only items you’ll wear almost every day of the year. I didn’t wear sunglasses a single day of my life until a few years ago. After feeling the sweet relief they provide, there’s no going back.

A good pair of shades can be as functional as they are stylish. Look for a quality pair that’ll be both durable and comfortable. Going with the cheap drug store glasses will just lead to frequent replacement and you’ll never be completely satisfied with the purchase.


Design

Lucky for us, sunglass designs have remained fairly constant over the years. Sure, some designs come in and out of fashion and proportions change a little, but it’s easy to find a pair that you won’t be ashamed of in two years. Look at images of actors like Steve McQueen and Cary Grant. The glasses they wore in the 1960’s are the ones you should buy today.

Aviators - These look good on the vast majority of people. They do great things for the wearer’s confidence, too.

Plastic frames - Round lenses and Wayfarers are classics that look as good today as they did 50 years ago.

AVOID - Sport frames. They’re fine for motorcycles and outdoor sports, but look out of place in daily life.

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Frame Materials

Lens Materials

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How to wear

The beauty of a classic pair of shades is that they go with everything in every situation from lounging at the pool to meeting with business clients. A single pair can be all you need, although more wouldn’t necessarily hurt.


SEE Eyewear - Great bang for your buck. Italian acetate framed shades starting at $99. My wife buys her prescription glasses here and they’re better and cheaper than anywhere else. Selection changes often.

Amazon - You can get some good deals here, but beware of knock-offs.

Nordstrom - Like every other item, department stores have endless variety.

Zappos - Lots to choose from here.

J.Crew - They actually carry a pair with the model name “timeless.” Coincidence?

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The Classic Timepiece

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A quality watch is probably the first thing that comes to mind when thinking of wardrobe investments. Also, probably the item most commonly passed down from father to son. You can wear it everyday, making cost per use almost negligible, so this needs to be something you absolutely love.

This can be a big purchase, and you could write an entire textbook detailing the different types of movements, material selection, and merits of different features and manufacturers. If you wish to dive that deeply (it’s highly encouraged if you do) then there are numerous sites and forums, like this one, that can provide you with in depth information.

The purpose of this chapter is to get you thinking about what style of watch will work best for you. I’ve been wearing a Timex Chronograph, every single day, for the past 5 years. Not a high end watch by any means but, with the exception of a single battery replacement, it’s been completely maintenance free. And it’s one of my most complimented pieces.

You’ll want to look for something that can work in almost any occasion you’ll likely come across. The single watch I own has been worn to fancy cocktail parties in downtown Chicago, while training clients in the gym, and kayaking in Oregon.

This is the kind of versatility that we must strive for to maximize our wardrobes and our dollars.

What to look for

Material

The case is going to be made of some type of metal. It doesn’t really matter which type you choose as long as you like the look. If you’re looking for a splurge, feel free to pay the extra money for a precious metal if that’s important to you.

Band Type

My number one recommendation is to AVOID a watch with an integrated bracelet.

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Since the unique lugs are part of the case, they only match one particular band. This style prevents you from being able to make easy changes.

As long as your watch has a standard pin attachment at the lugs, it doesn’t matter which type of band the watch comes with. You can, and should, change it anytime you want.

This is the key to versatility.

All you have to do is invest in one classic face and you can have a black alligator band for formal occasions, brown leather for daily use, and nylon for casual and outdoor activities. Switch them out with an inexpensive pin tool and you have a complete watch wardrobe.

Face Size

Look for a size that fits your body proportions. A smaller watch will look dainty on a big guy and a huge face will be overpowering on a slimmer man.

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When measured across the face, 35mm is considered small, 40mm medium, and 45mm large. They will either be labeled or the person at the counter should be able to help with this.

Face Design

A round face will be most versatile and never goes out of style. A simple face is the most formal, while a series of dials and secondary functions leans towards the casual/sporty side. I would just recommend that you stay away from the extremes, being completely plain (numberless) and having more functions than your smartphone.

Movement

Mechanical or Quartz?

Wars have been started over such questions. Mechanical (automatic) watches are more expensive and get their power from either manual winding or automatically through the swinging of your arm.

Quartz movements are battery powered and less expensive.

As a general rule, if this is a watch you plan to pass down to your son, go with a mechanical movement.

If you’re not confident you want to invest in a watch you’ll wear for the rest of your life, it’s okay to go with a quartz. Just know that if you become attached to it, it may give out before a mechanical movement would.


Local Jeweler - For major purchases, it’s nice to have the security and support of a local professional.

J.Crew - A little pricy for quartz movements, but damn those watches are fine.

Zappos - Plenty to choose from at many different price points. Great customer support to boot.

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Amazon - A great place to get a Timex or Fossil, but beware of knockoffs when it comes to high end watches.

Nordstrom - Plenty to choose from. Just do some research and try not to pay too much for that “designer” name.

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The Quality Bag

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Nothing can spoil a refined look like lugging around a cheesy, “tech” fabric backpack on your way to the office. Finish off your look with a classic, masculine, and stylish bag. Depending on your needs, this can be a backpack, duffle, tote, or briefcase.

Sticking with the investment theme, a quality bag isn’t something to be replaced with the changing of the seasons. With daily use, you should get at least five years out of your purchase, and a lifetime if only used for occasional travel.


Materials

Natural materials will serve you best in this department. Think leather, canvas, and wool with metal or wood accents. What you’re looking for is an item that will develop a beautiful patina over its lifetime.

Design

Avoid anything that looks like it came from an office supply store or a backpacker magazine (vintage being the exception). I love lightweight backpacking equipment, but it has no place on the city streets.

Many companies take cues from the military, outdoor gear, and high end designers, but by the time these styles trickle down to the masses, they’re complete abominations of the original and are best avoided.

Simple is best in this department.

Retro outdoors and mountaineering is a great place to start. If it looks like your grandfather could’ve carried it when he was a young man, it’s probably a safe bet.

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How to wear

Your everyday bag should go with what you wear on a consistent basis.

If you’re a suburban high school teacher and wear jeans and a tweed blazer most days, buying an uber sleek black leather, chrome-accented briefcase wouldn’t be the appropriate choice. Leave that look to the lawyers in Manhattan.

In the situation above, you’d want something in a brown leather to complement your overall look.


J.Crew - They have their own brand of bags and also have a rotation of featured heritage brands. All solid choices.

Zappos - The possibilities here are almost endless.

Nordstrom - A.P.C, Barbour, Jack Spade, Herschel Supply Co.

SuitSupply - High quality and extremely sharp leather goods.

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What to Do Now?Assess your current wardrobe

Do you already own any of these pieces? If so, great! Anything that can be substituted would also be a welcome addition. For example, a pair of brown desert boots would be a great substitute for the brogues if you’re a man who dresses exclu-sively in casual attire.

Decide which items are most important

Not everything on the list is going to be equally beneficial to you. I suggest that you rank them in order of most to least im-portant and then start at the top of the list.

Try things on in person

Whenever you have the opportunity, handle items in person and try them on. This is the only way you’ll find out what works for you and meets your quality standard. I, for example, think double rider jackets look really great on some people - but when wearing one, I feel like a complete goofball. Glad I didn’t just buy one on eBay without trying it on.

Create an idea board

No longer do we have to clip pictures from magazines and tape them to the wall. On Pinterest, you can organize any picture from the internet onto a single board to keep all of your ideas organized. Take a look at mine here to see an example and get inspired.

Set a budget

Not everyone can just go out and drop $5,000 on a new wardrobe in a single afternoon, and that’s okay. The best way to go about this is to decide how much money you can set aside each month and then allocate that to the items of highest impor-tance on your list.

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Seek out the perfect piece and buy

Once you know exactly what you want and have the money set aside for the purchase, don’t hesitate. The idea is to start dressing better and boosting confidence as soon as possible.

Enjoy and care for your items

Some people claim that the excitement of a new purchase wears off after an hour or so. I completely disagree. Every time I pick up a pair of my shoes, a smile creeps across my face. Just ask my wife. The same smile can be seen while polishing my shoes, conditioning a leather jacket, or ironing my shirts.

Don’t forget to wear often!

There’s nothing worse than an expensive suit or pair of shoes that spend more time collecting dust than being proudly donned in the real world. Suits were meant to be worn, not protected like some priceless work of art. On the plus side, most of the items on this list will get better the more you wear them. It’s a win-win situation, for sure.

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I hope you’ve enjoyed reading this guide as much as I’ve enjoyed writing it!

If you have any questions stop by ironandtweed.com and leave me a comment or contact me using the site’s contact form.

Also if you know anyone else who would enjoy this guide, please point them to the blog or use the sharing links on the fol-lowing page so they can pick up a copy for themselves.

In addition to this guide you can also check out my complete ebook on how to build an affordable wardrobe:

CASUAL STYLE 101 - THE AFFORDABLE WARDROBE GUIDE

Thanks for reading!

- Nate

Conclusion

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10 timeless wardrobe essentials

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