Looking to (re)build your wardrobe? Start here:
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So how do you use this guide?
We’re not recommending individual products or brands here. We believe that process should be a lot more personalized. Instead, we’ve included images from the following brands for illustrative purposes only. Truthfully, these brands all run the gamut in terms of price and fit. We only suggest you use the categories in the guide as a sort of shopping list that you’ll find products against.
Many of you will also gravitate towards one category over another. For example, you might really love sweaters so you could stock-up on those and perhaps pass on the flannels. That’s totally fine!
Of course, if you need help finding personalized recommendations tuned to your fit, size, budget, and brand preference, that’s where we come in!
Ok let’s get started:
Shirts
OCBDs - Oxford Cloth Button Downs - (x2)
OCBDs are some of the most versatile shirts out there. Made in an oxford weave that provides the perfect amount of texture that is easily dressed up or down. These shirts have button-down collars that should always be buttoned-down
We recommend getting one in white and one in a French blue (or even a blue/white stripe if you want a bit more pattern).
📷: asket.com
📷: taylorstitch.com
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Washed Poplins (x2)
Not many brands and retailers will call them poplins or washed poplins but what you are looking for is the smooth material that feels sort of like your bed sheets. They often have a wash to them that makes them extra soft as well. And if you are into plaids, patterns, or prints, these are the kinds of shirts where you’ll find that!
These are great for wearing by themselves or layered with a sweater or vest.
📷: bonobos.com
📷: jcrew.com
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Dress Shirts (x2)
No, not dresses in the form of shirts, but shirts you wear to dress-up, like with suit or at least wool trousers. These can be made in a range of fabrics but are usually poplins, or slightly textured dobbys.
A general rule of thumb when figuring out if a shirt is casual vs. dressy is to look for wash and/or texture. Wash and texture usually indicate a shirt is casual while dress shirts are often crisp and smooth. The shape and size of the collar also give you clues. For example, button-down collars are almost always casual while spread or semi-spread collars can be dressy!
📷: charlestyrwhitt.com
📷: mizzenandmain.com
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Flannel/Brushed Twill Shirts (1 - 2)
This addition to the list is one of the more seasonal options, although depending on your geography, you can likely get away with wearing a flannel or brushed twill shirt for at least 3 out of the 4 seasons (so long as it’s not an overly seasonal plaid i.e. any combination of red).
If it’s a bit on the warmer side, flannels can be great layered over a t-shirt with the buttons left open.
Flannels are generally a more casual shirting option although there are some flannels out there with less brushing that can be worn for a more dressed-up occasion.
📷: llbean.com
📷: bonobos.com
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Denim/Chambray Shirt (x1)
These shirts are my personal favorite, and I’m guilty of rocking the “Canadian Tuxedo” a few too many times. This shirt is the epitome of “dressed-up casual” meaning “I’d rather be wearing a t-shirt right now, but I have the respect to wear a button-up shirt for this occasion.”
You’ll find these in multiple washes, mostly in shades of blue but sometimes gray ones as well. I’ve always liked a slightly darker blue wash that fades a bit overtime and comes into its own as you wear it.
These shirts go great with olive chinos, black chinos or denim, and yes even blue jeans! If you do wear it with jeans, we recommend your shirt be a lighter shade than your pants.
📷: clubmonaco.com
📷: bananarepublic.gap.com
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T-Shirts (x4)
The tried-and-true staple of your closet – the t-shirt. It used to be that t-shirts were more of an undergarment or something with a graphic on it that you wore on the weekends, but now t-shirts can be a perfect top for all sorts of occasions.
You’ll likely gravitate towards a single t-shirt silhouette you like (Crew neck, V-neck, or Henley). That’s fine. I’m partial to crews and henleys, but wear what you are most comfortable with.
If you are wearing it alone (i.e. nothing on top of it), we recommend finding a heavier weight t-shirt so it feels a bit more substantial. Also, don’t be afraid to get something a bit longer than you might be used to. If you lift your hands up, your stomach shouldn’t show.
📷: everlane.com
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Long Sleeve T-Shirts (x2)
Another potentially seasonal choice, long-sleeve t-shirts are a great staple to have in your wardrobe. You’ll often see them made of the same material as common t-shirts (called jersey) or with a bit of texture like waffle or rib stitching (the latter two being the most seasonal choices).
Long-sleeve tees can and should be worn by themselves or underneath a cardigan or light jacket.
📷: buckmason.com
📷: gap.com
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Sweaters
Shawl Collar Cardigan (x1)
This could easily go in the outerwear section below, but either way, a shawl collar cardigan sweater is a cozier outerwear alternative that you’ll be wearing all Fall and Winter. They come in a range of materials, some with wool, some with just cotton. These are a perfect way to add some texture to your wardrobe as well.
These are great layering sweaters. Wear it casually over a short-sleeve or long-sleeve t-shirt, or dress it up a bit over an oxford.
📷: fahertybrand.com
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Crew Neck Sweater (x2)
Some guys will want to put V-neck sweaters in this slot instead. V-necks are fine when worn over a button-up shirt, but we don’t recommend wearing them alone or over a t-shirt. It’s just kind of a weird look.
The crew silhouette is a lot more versatile as it can easily be worn alone or dressed-up with a button-up shirt underneath. Like all sweaters, these come in a range of materials. If for some reason you don’t like wool or wool blends, there are plenty of 100% cotton options that will work just fine!
📷: naadam.co
📷: roddandgunn.com
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Sweatshirt (x2)
OK, so this technically isn’t a sweater. We left this one kind of open in terms of silhouette. Some people like crew-necks, some people like hoodies, some like their hoodies in the form of a full-zip. Pick your favorite and grab a couple (or mix and match). This is an excellent casual layering piece that you’ll probably find yourself rocking on the weekends more than anything.
This is your first line of defense for cooler weather. It’s easy to pull on and off and doesn’t make you so warm that you’ll regret having it on you in the middle of a Fall day (cool mornings, warm days).
📷: american-giant.com
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Pants and Denim
Denim (2 - 3)
This is probably the article of clothing that men struggle with the most. You either love them (because they fit perfectly) or hate them (because they don’t fit right). Finding a pair of jeans should be 99% based on finding something that fits you perfectly. The other 1% is consideration of the price which, we think, is not that important. If you find either a brand that fits you well, or a certain pair – just get them! It will be money well-spent.
In terms of color (called wash when speaking about denim), we recommend something called “rinse” (like the picture below), which is a slight wash that doesn’t fade the color of the original denim. This is a dark pair of denim that is easy to dress-up or wear casually and it goes with everything else in your closet.
For your second pair, you can either get a medium wash or even a pair of gray denim to extend the range of your wardrobe. We’re hard-pressed to think of anything that won’t match with either choice.
📷: paige.com
📷: nudiejeans.com
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Chinos (x2)
You might know them as khakis, that’s OK, but their real name is “chinos.” Khaki is a color that you’ll often see in a chino. Chinos are most commonly cotton twill pants with slanted or angled pockets pockets. They are a slightly dressier version than their 5-pocket cousin, but even a chino with a fair amount of wash on it qualifies as a casual pant.
Fit is critically important here (like in all bottoms), so find a brand or a pair that works for you a grab a couple of colors (navy, gray, dark khaki, olive, etc.). This will be your preferred pant if you have “business casual” office environment or are looking for a slightly nicer pant for a night-out.
📷: bonobos.com
📷: perkclothing.com
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Technical Pant (x1)
This might be the most “out-there” recommendation in this guide, but it probably is the one I am most passionate about. This type of pant will change your life as it likely is the most comfortable option (besides a pair of fleece sweatpants).
These pants are the epitome of versatile and can be worn walking the dog on the weekend or even with a dress-shirt to work. They are usually made with some combination of polyester, nylon, viscose, spandex. Don’t be afraid of that! Those man-made fibers help provide some technical attributes to the pants like wicking, quick-dry, anti-odor, and stretch.
You’ll wear these instead of jeans and chinos, so we recommend grabbing a different color than your favorite chinos – even if it’s just a slightly different shade!
📷: lululemon.com
📷: westernrise.com
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Suiting
Suit (x1)
Every man should have a suit in his closet that fits, is well-maintained, and is ready to go at a moment’s notice. Too often we see guys wait until the last minute to get a suit for an upcoming event after realizing that the one they had doesn’t fit anymore, is out of style, or has moth holes from lack of care. Once you are 25+ and pretty much done with growing (north-south), make the investment of getting a well-made suit. You might not wear it often, but when you do, you should be looking your absolute best, and nothing helps that more than a well-made, well-fitting wool suit.
In terms of color, you really have two options, navy or gray/charcoal. It really comes down to personal preference. Don’t get a black suit, there are only a handful of occasions where that’s appropriate.
📷: suitsupply.com
📷: brooksbrothers.com
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Wool Trousers (x2)
When you don’t need to wear a full suit, but still need to dress up, look no further than a pair of well-fitting wool trousers. Made of the same material that all quality suits are made of wool trousers (without a matching jacket) are your go-to option for slightly less formal-than-a-suit occasions.
We recommend a bit of strategy here to maximize the versatility of your wardrobe. Whatever suit color you get (choose that first), get a different color trouser. You can always wear your suit trousers without the jacket as another pant option!
📷: spierandmackay.com
📷: toddsnyder.com
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Ties (x2)
Depending on your job (or how many weddings you get invited to), you might need a whole lot more than 2 ties. At the bare minimum, you should have two. We recommend getting one solid colored tie (navy, purple, red, light pink) are all great options. These will be for any job interviews you have or if you get invited to a more conservative wedding or religious event. For the second one, you should have a little more fun. Minimally that means a pattern of sorts, or if you’re up for it, find one with a subtle floral pattern.
📷: thetiebar.com
📷: charlestyrwhitt.com
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Outerwear
Outerwear can be personal. We get that. You probably already have a few favorites, or at least some favorite silhouettes. You might find that some of the below options you would never wear. That’s fine too. We can find you some more personalized options, but for now, here are a few classic silhouettes to consider.
Chore Coat (x1)
There isn’t a singular definition of exactly what a chore coat is, but some key commonalities are patch pockets (at least 3), a stand collar, and button closures. Some of our favorite chore coats have workwear vibes which means they’ll stand up to the elements. Even still, don’t be afraid to wear this to a dressier occasion especially if you opt for a darker color with less wash or texture.
📷: filson.com
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Field Jacket (x1)
Like other outerwear, the exact description of a field jacket eludes us, but essentially, it’s a lighter weight jacket with 4 pockets on the front and a zip closure. Because it’s lighter weight, it’s great for layering. Many brands will make them with as a cotton jacket with a wax coating which provides protection from wind and water.
While some field jackets could be dressed-up, this is definitely a more casual option that works best worn with jeans or chinos.
📷: barbour.com
📷: huckberry.com
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Wool Coat (x1)
You’ll see a bunch of different names like car coat, top coat, driving coat, etc. Find a silhouette you like, which usually means deciding how many pockets are on the outside, and look for something that is mostly wool. These coats will usually come as a solid color or with a bit of a textured pattern like a herringbone or houndstooth. This is the coat you’ll wear when it’s cold out and you need to dress up a bit (think going to a nice restaurant or a show).
📷: theory.com
📷: tedbaker.com
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Shoes and Belts
Sneakers (x2)
So, this might be the most personal section of this whole guide. Some dudes love sneakers, some dudes couldn’t care less about them. Some people love certain brands of sneakers, other hate those same brands. Whatever your perspective, we recommend you find a couple of sneaker brands you like and grab a few pairs.
We love recommending a clean white sneaker (many brands offer them). It’s the perfect shoe that can be dressed-up or worn casually. It also goes with almost all of the pants in your closet. Trust us, just pick up a pair and we bet you’ll be grabbing them out of the closet more than you think!
📷: greats.com
📷: allbirds.com
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Derbies (x1)
The dress shoe that doesn’t have to be dressy! Ok, so they are dressier than the sneakers above, but this is the shoe that you’ll wear with your chinos or jeans when you’re headed to the office or out on a Friday night. We admit, derbies and oxfords (below) look very similar. The main noticeable difference is the leather pieces (called quarters) that are sewn on top of the vamp (the main part of the shoe). On oxfords, the quarters are sewn under the vamp.
Derbies can have ornamentation on them (called broguing) for a bit of added character and texture. This also makes them more casual. Suede or nubuck can also be great options!
📷: beckettsimonon.com
📷: clarksusa.com
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Oxfords (x1)
This is the dressiest shoe in your closet. Most people think that oxfords shouldn’t be worn with anything but a suit. Here, we’re not a fan of hard and fast rules in fashion, but we just thought you should know that. Depending what color suit or dress pants you opted for above, you have a few options here, but we think a dark brown is probably the most versatile choice.
Also, these are something you want to invest in. We get that everyone has different budgets, but with dress shoes, you get what you pay for. It’s best to push your budget a bit here. Otherwise, you’ll be spending more when you have the buy a second pair because the first ones broke.
📷: allenedmonds.com
📷: meermin.com
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Boots (x1)
We think boots are the perfect item to let other people know that you know about style and fashion. A seasonal choice, boots should be your go-to option if the weather is south of 50 degrees. There are a few different silhouette options like plain-toes, cap-toes, moc-toes, chukkas, and chelseas. And it’s true that each silhouette lands on a slightly different places on the dressy to casual spectrum. Even so, find a quality pair that fits you and is comfortable and start rocking these all Fall and Winter long!
📷: thefryecompany.com
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Belts (x2)
You should always wear a belt unless you’re intentionally not wearing a belt which shouldn’t be too often. As such, you’ll probably need more than 2, but at the very least you should have a casual option (worn with jeans and chinos) and a dressy option (worn with your suit and dress pants).
Your dressy option should match, almost exactly, with the oxfords you chose above. Look for silver hardware to make it easy. This belt should also be slightly thinner than your casual choice.
Your casual option will generally be wider, and the hardware will be a bit chunkier and less shiny. A dark brown will go with everything.
📷: shinola.com
📷: magnanni.com
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So is this list comprehensive? No! There is so much more that we could have added like activewear, technical gear, shorts, accessories, and even more options within these categories! But that stuff starts to get a lot more personal, and we don’t want to overwhelm you. Plus, your occupation might call for slight adjustments to this (i.e. more suits, less sneakers).
Either way we think this is a great start if you are building your wardrobe for the first time or are re-building it after some time away from your closet.
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