Here’s How to Construct a Basic Male Wardrobe With 23 Classic Pieces
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Let’s get one thing out of the way with right off the bat — there’s no such thing as an ‘ideal’ male wardrobe.
Anyone who tries to tell you otherwise is fooling themselves. There are infinite different ways to dress yourself, and if you feel good wearing something, that makes it worth wearing.
But that doesn’t mean people aren’t interested in how other people dress — and often that’s a gendered phenomenon. Whether you’re trans or cis, being a guy often entails looking like a guy, and just as there’s nothing wrong with wearing feminine clothing, there’s nothing wrong with opting for a more rugged, masculine look either.
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But what does that rugged, masculine look entail, exactly? Well, it varies from culture to culture, and it can change significantly over time.
But if you wanted to make a shopping list of every basic male wardrobe staple for contemporary Western men for an alien who was trying to start a clothing collection from the ground up, what would be on it? Here’s our breakdown of the classic menswear staples we think guys can’t do without.
Classic Men’s Bottoms & Legwear
They’re not super fancy, but most days don’t call for fancy. Jeans are tough, durable, and can come across as both neutral and slightly dressy, depending on the color, level of wear, and fit. They’re a core part of the contemporary male wardrobe.
AskMen Likes: Levi’s 512 | Lee Regular Tapered | Todd Snyder Slim Fit Stretch
Like jeans, chinos can read as casual or chic, depending on a handful of factors. They pair well with cooler tones — a dark blue top, and a pair of khaki chinos is a classic combo that every guy seems to be able to pull off.
AskMen Likes: Everlane Performance | Flint & Tinder 365 | Bonobos Stretch Washed
When the temperatures rise, so should your hemlines. There’s no need for your calves to be sweating it up — unless you live in the far north or ski full-time, you’ll need a few pairs of shorts to bust out during the summer, whether they’re more laid-back, more performance-oriented or even edging a little bit into formal territory.
AskMen Likes: Duer Journey | Specialized/Fjällräven Hybrid | Nathan Essential
Hard pants are basically a necessity, but let’s be frank — they’re for outdoor use. If you’re staying in all day, you’ll want a cozy pair of soft pants to lounge around in. Enter the sweatpant. Ideally it’s got some stretch to it, will keep your legs warm and may even be wearable for a trip down to the corner store in a pinch.
AskMen Likes: True Classic Joggers | tentree Atlas | John Elliott Escobar
Maybe you’re militant about going commando, but for the majority of guys, underwear is a must. Boxer briefs are a great compromise, and ones like these, with a crotch pouch, allow you to get the best of both worlds — a snug, comfortable fit without any tightness.
AskMen Likes: AllCitizens Elite II | Ministry of Supply Merino | BN3TH Cascade
Like shorts, swimsuits are a summer staple. There’s a good chance you only need one pair of these, but you do need it. Ideally, you want something that’s a good midpoint between covering your knees, and showing off the ends of your pubic hair. A little stretch wouldn’t hurt, either.
AskMen Likes: Bugatchi Max | BN3TH Agua Volley | Chubbies Classic
Classic Men’s Tops & Outerwear
Let’s face it — the T-shirt is the jeans of the torso. You probably already own a dozen of these, if not several, and many of them probably have designs on them that represent a distinctly younger version of yourself. In fact, for many guys, the challenge here might be to keep your rotation fresh, rather than relying on increasingly ratty tees from years past.
AskMen Likes: Proof 72-Hour Merino | Buck Mason Field Spec | True Classic V-Neck
Tees are awesome, but they can’t do the job alone in the colder months. You’ll need something to go over them, and sweatshirts and hoodies are your friends here. They’re sort of like sweatpants for your chest — you want some stretch, some cozy vibes, and some warmth. Also, this should be something you’re prepared to have stolen from you by a romantic interest.
AskMen Likes: True Classic Hoodie | Vuori Coronado | Gap Vintage Soft Crewneck
Sometimes, you want to be warm and look like a rugged fisherman. There’s no harm in that. That’s what cable-knit sweaters are for. They don’t boast the versatility of a sweatshirt, and you probably don’t want to do that much actual sweating in them, but damn, are they cozy when the situation calls for one.
AskMen Likes: Sunspel Jumper | L.L. Bean Fisherman | Patagonia Crewneck
Work in a professional setting? Going on a nice date? Need to impress someone — or several? You’re going to need a dress shirt. Depending on your lifestyle, one or two might be enough — or you might need a dozen-plus. You can take advantage of variations in fabric and go for some that are a bit fancier, while others are a bit more casual.
AskMen Likes: Charles Tyrwhitt Twill | Scotch & Soda Linen | Ministry of Supply Aero Zero
Is it hot outside and you’re trying to split the difference between a semi-formal look and not sweating your balls off? You need a short-sleeved button-up shirt. It probably has a cool pattern or a non-boring color, and it’s just right for looking nice on a summer night. Or day.
AskMen Likes: Chubbies Friday | Bugatchi Miles | Uniqlo Polo
On the flipside, if you want some of a dress shirt’s gravitas, but you need to stay warm, you’re going to want a flannel. This could range from a more dressy version to an all-out shirt jacket that’s intended to be worn for hard-nosed manual labor. But if you’ve got more than one, at least one of them should be plaid. Those are the rules.
AskMen Likes: Roots Bellwoods | LinkSoul Wyeth | Faherty Brand Sherpa Plaid
Whether it’s a Letterman jacket, a leather jacket, a bomber jacket or a jean jacket, a good jacket is a key piece in any guy’s toolbox of looking pretty cool. Depending on where you live, these might be more for looks than for keeping you warm, but either way, being able to take it off and wrap it around your date’s shoulders is an old-school move with no small amount of romantic cachet.
AskMen Likes: Levi’s Sherpa Trucker | Nobis Maize Bomber | Dickies Chore Coat
Classic Men’s Footwear
Need to get somewhere in a hurry? Whether you call them kicks, tennis shoes, or running shoes, you’re going to want some casual footwear you can sweat in — and possibly beat the hell out of. They should be comfortable first and foremost, but it doesn’t hurt if they also look cool.
AskMen Likes: Nike Blazer Mid | Cole Haan Zerøgrand II | Tropicfeel Sunset
On the other end of the spectrum, a good pair of dress shoes is necessary, because sneakers are typically frowned upon at weddings, funerals, and most reasonably nice social occasions. Since you won’t be playing sports in them, or wearing them very often, they don’t need to be remotely as comfortable — here, what you want is looks and durability.
AskMen Likes: Cole Haan Wingtip Oxford | Hartt Beaverbrook| Bruno Marc Oxford
If you live in colder climes, or if you’re an old-school guy who likes getting his hands — and feet — dirty, a good pair of boots is a must. You’ll likely want something in leather, with a sort of rugged air and the ability to withstand several years of abuse.
AskMen Likes: Allen Edmonds Freeport | Dr. Martens Chelsea | Red Wing Classic Moc
Classic Men’s Accessories
A belt is more than just a means of holding your pants up — it’s also a potential opportunity to insert a little pop of color into your look, as well as a means of inserting some solidity into your outfit. A man who’s sporting hard pants and a belt? He means business. Ideally, you want leather, or vegan leather — fabric belts can look flimsy and cheap.
AskMen Likes: Perry Ellis Portfolio | Doshi Vegan Leather | Timberland Classic
Hats are more than just fashion accessories — they’re also great at covering up bedhead and bald patches, as well as offering you protection from the elements and a means of telegraphing which sports team you support, if applicable. You don’t need to own more than two, but to only have one or none seems foolhardy.
AskMen Likes: New Era Spice Fitted | Merrell Rib Beanie | lululemon Days Shade
If you’re not quite secure enough in your masculinity, to wear other forms of jewelry — and let’s be honest, most guys aren’t — a watch is a great way to add a little note of niceness to your look in an inconspicuous kind of way. Plus, little-known fact, they can also tell time.
AskMen Likes: MVMT Legacy Slim | Casio G-Shock GAB2100 | De Tomaso Sorpasso
A good wallet will hold everything you need in it and nothing you don’t. There’s nothing worse than toting around a slowly growing chunk of leather, whose sheer size and weight start to impact your posture. The current trend in Wallace is thankfully a sharp turn away from this concept, prioritizing, slim and sleek.
AskMen Likes: Bryker Hyde Bifold | Bellroy Flip Case | Buffway Minimalist
Broadly speaking, when it comes to carrying stuff that’s too big for your pockets and too important to leave at home, a backpack is your go-to. (Of course, if you’re fancy, a briefcase isn’t out of the question.) But carrying your possessions on your back is a great way to keep your hands and arms free, and a nice, and a modern backpack that doesn’t look like you put it through academic hell isn’t out of place on guys of almost any age these days.
AskMen Likes: Bellroy Transit | Peak Performance Everyday | 8000Kicks Everyday
Classic Men’s Formalwear
If you’re a lawyer, or millionaire, you might have a whole closet of these. Most guys can get by with just one full suit, with maybe a spare blazer to boot. But if your budget allows, two or three full suits gives you some breathing room, in terms of not having to wear the same one into the ground every time you need to dress up.
AskMen Likes: SuitSupply Lazio | xSuit 4.0 | Wills All Seasons
Neckties are definitely less of a male wardrobe staple than they used to be. You don’t need one around your neck five days a week unless you really want to wear one. But, as with a good pair of dress shoes, they’re an indispensable part of a complete male wardrobe. They offer you a chance to work some supporting colors into your look in a very classic way. When things get formal, a tie has your back. Or rather, front.
AskMen Likes: SuitSupply Silk | J.Crew Italian Wool | John Henric Cotton
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