The Modern-Classic Wardrobe in 60 Seconds:
If you only remember five things from this guide, make ’em these:
1. Favor timeless over trendy. Buy clothes that will still look good five years from now.
2. Balance classic and contemporary. Take inspiration from traditional menswear, sure, but adapt it to modern life.
3. Build an aresenal of versatile pieces. Every item should work with multiple other items in your wardrobe.
4. Prioritize fit over labels. A well-fitting $100 item will almost always look better than an ill-fitting $500 one.
5. Dress for your actual life. The goal isn’t to look like a fashion influencer or a 1950s businessman. It’s to look sharp in the world you really live in.
H ere in the first half of the 21st century, one could argue (and, spoiler alert, I’m about to) that it’s never been harder for men to look sharp and sophisticated.
Trends today come and go quicker than ever before, making it almost impossible to keep up with the latest fads.
And as if the rapid churn of social media didn’t make it hard enough, the challenge is further compounded by the fact that we live in a much more casual world than our fathers and grandfathers.
While they could just slick back their hair and throw on a tie whenever they needed to dress up, today looking sharp requires threading the needle between casual cool and smart sophistication.
That’s why I’ve long advocated for what I call the modern-meets-classic aesthetic.
Instead of obsessing over trends or dressing so old-school that you look like you’re auditioning for a period drama, the modern-meets-classic look splits the difference, combining the timeless style and sophistication of a classic gentleman with the technology, tastes and expectations of the modern world.
The result is a wardrobe that’s practical enough for modern life, while still evoking the style and sophistication of a classic gentleman.
Below, I’ve broken down the core wardrobe staples that form the backbone of a timeless modern-classic wardrobe that’s practical, versatile and, of course, sharp as hell.
Ummm, wait a second:
What Makes Clothes “Modern-Classic”?
As I alluded to above, modern-classic style sits at the intersection of timeless, contemporary, practical and sophisticated.
But the operative word there is “intersection.”
One thing that separates modern-classic style from something like the Old Money aesthetic is that it’s not really about maxing out on one particular variable, like timelessness. It’s about finding the sweet spot where timeless, contemporary, practical and sophisticated overlap.
So to evaluate a piece’s suitability for this wardrobe, I looked at it through four lenses:
Timeless
- Will it still look good five or ten years from now?
Contemporary
- Does it feel appropriate in today’s world, rather than belonging to a different era?
Practical
- Can it realistically be worn as part of a modern man’s everyday life?
Sophisticated
- Does it make you look more poised, polished and put together than the average guy?
The strongest modern-classic pieces tend to score well in at least three of the four categories.
A peacoat, for example, is timeless, practical and sophisticated. Hybrid shoes are contemporary, practical and sophisticated. White leather sneakers are timeless, contemporary and practical.
You get the idea.
The Modern-Classic Scorecard
How the core categories in this wardrobe stack up against the four pillars of modern-classic style
As the chart above illustrates, no piece, and in fact no category of menswear is perfect. But the pieces listed herein consistently do the best job of combining the qualities that define modern-classic style.
OK, enough preamble! Let’s get to the wardrobe.
Outerwear
As I wrote in my book Sharp as Hell, neglecting outerwear is both one of the most common and most costly style mistakes.
“A lot of guys tend to think of outerwear only as an afterthought, if they think of it at all,” I wrote. “But that’s actually a big mistake, because… a well put together outfit won’t do you much good if you cover it in a coat that fits poorly, clashes in color or isn’t situationally appropriate.”
So, you’re probably already ahead of the game if you’re putting proactive thought into your outerwear.
But you accelerate your advantage even further by avoiding trends and opting for modern-classic pieces that have stood the test of time, and pair just as well with contemporary casual clothes as they do with traditional menswear staples.
Wool Coats
With wool coats, the emphasis is slightly stronger on the “classic,” part of modern-classic, which is what makes them so deadly.
Versatile, timeless and effortlessly sophisticated, wool coats are one of the few pieces that look just as good on us as they did on our grandfathers.
While there are a number of varieties available, there’s really no reason to over-complicate things when assembling your wardrobe.
Both the knee-length overcoat and peacoat are classic, can’t-miss pieces that look great on every guy.
Both are “dressy” enough to be worn with a shirt and tie, but can also pair just as well with a t-shirt and jeans for an elevated smart casual look.
Peacoat
Overcoat
Midweight Casual Jackets
The menswear industry would love for you to believe you need five different “statement jackets” every season. You don’t. You need a handful of versatile pieces that look good now and will still look good five years from now.
With midweight jackets, opt for lightweight, versatile styles that are easy to layer, and provide an elevated look without feeling overly formal or trend-driven.
Harringtons, bombers, field jackets, trucker jackets and overshirts all strike a great balance between classic heritage style and modern wearability.
Minimal Overshirt
Trucker Jacket
Field Jacket
Leather Jacket
When done well, leather jackets combine rugged masculinity with understated sophistication, which is why they’ve remained a men’s style staple for nearly a century now.
Clean, minimalist styles add character to casual outfits. And if you choose the right style, you can wear it for years without having to worry about it going out of date.
Pilot Bomber
Cafe Racer
Blazer/Sport Coat
There may be no single garment that better encapsulates the modern-classic look than a well-fitted blazer or sport coat.
As the natural bridge between casual and formal dressing, they instantly sharpen an outfit, but make no mistake: throwing on a sport coat doesn’t mean you have to look stuffy.
Quite the opposite, actually. My favorite move is to go with a softly tailored version with little-to-no shoulder padding, which avoids the “I couldn’t find my suit pants” look in favor of a modern silhouette that’s both comfortable and versatile.
Cold-Weather Outerwear
I live in Canada, where the winters frequently get so cold that even thick sweaters and wool overcoats aren’t enough to keep out the cold.
When the weather’s that frigid, the best way to adhere to the modern-classic aesthetic is to ask yourself one simple, but immeasurably important question:
How would James Bond bundle up?
The answer tends to be with the most stylish and sophisticated version fo parkas, puffers and quilted jackets.
What counts as stylish and sophisticated in this space?
Think muted colors like dark gray, green, blue or black, clean silhouettes that avoid unnecessary bulk, and minimal branding that doesn’t make you look like a walking billboard.
Parka
Puffer Jacket
Quilted Jacket
The modern-classic wardrobe combines the timeless style and sophistication of a classic gentleman with the technology, tastes and expectations of the modern world.
(plus, it looks sharp as hell)
Tops
T-Shirts & Henleys
Foundational, versatile and perennially stylish, the humble T-shirt is one of the hardest-working garments a modern-classic man can own.
But don’t let its simplicity fool you.
A great T-shirt can make you look effortlessly masculine and put together. A bad one can make you look like you grabbed whatever was on top of the laundry pile.
As always, fit is king. Look for clean lines, quality fabrics and a silhouette that skims the body without clinging to it.
And when it comes to colors, simple beats novel every time. Neutral shades like white, gray, navy, olive and black will serve you far better than whatever graphic tee seemed funny three years ago.
Polo Shirts
Occupying the perfect sharp–but-not-“dressy” sweet spot between a T-shirt and a button-up, a good polo makes you look refined and put together without sacrificing comfort.
Of course, “good” is the operative word.
While fit is obviously important here, the type of polo you wear plays a huge role in determining the vibe you give off. For my money, the best ones offer a combination of structure, stretch and stylish details that help them stand out from the golf-shirt wearing masses.
Button-Up Shirts
It would literally be impossible to build a modern-classic wardrobe without a few good button up shirts.
But note that I said button up, not button down. (Yep, there’s a difference.)
Which style you should load up on will depend heavily on your day-to-day.
If you work in a formal office environment that requires suits or business casual wear, you’ll probably want to make sure you’re well stocked on dress shirts. Personally I tend to favor the wrinkle-resistant kind, because ironing is a bitch.
But if, like me, you spend most of your time in more casual settings, than loading up on casual styles like Oxford cloth button-downs, chambray and linen shirts could make more sense.
Sweaters
A man’s sweater says more about his style than any other piece of clothing, save for maybe his shoes (on which more below).
Why? Because they make it so easy to look sharp.
A wool shawl collar is just as warm and comfortable as a hoodie, but it makes you look [checks notes to confirm the math] about ten gajillion times more poised, polished and put together.
That’s why it says so much about you: it’s a force multiplier.
Throw on any of the modern-classic styles below, and you’ll immediately look like someone who values himself more than the guy in a neon hoodie.
And when your look says “I value myself,” other people tend to value you, too.
Crew Neck
V-Neck
Long-Sleeve Polo
Shawl Collar
Cardigan
Quarter-Zip
Sweatshirts & Athletic Sweaters
Knowing how to nail athleticwear is essential for this day and age, because it’s one of the things that distinguishes modern gents from our forebears.
Fitness culture is rampant, and most of us have embraced it. But just because you’re dressed athletically doesn’t mean you can’t be dressed aesthetically.
To thread the needle between sharp and sporty, keep the silhouettes slim, the colors dark and the logos to a minimum.
Simple designs in quality fabrics can wick just as much sweat, but offer a more refined alternative to heavily branded or trend-driven athleisure.
Pants*
(*I’m sorry, but I refuse to call them “bottoms”)
Chinos & Casual Trousers
If there’s one category of pants that best embodies the modern-classic philosophy, it’s chinos and casual trousers.
Comfortable enough for everyday wear, but easy to dress up with a smart shirt and a sharp pair of shoes, they occupy the perfect stylish-but-not-too-stuffy sweet spot between jeans and dress pants.
Once you find a brand or style you like, load up on a few core colors (khaki, gray, navy and black are always good places to start) to form the basis for a versatile, timeless look.
Medium-Wash Jeans
Recommending medium-wash jeans may be the most controversial bit of style advice I’ve ever given, which is ironic, because they’re about as straightforward and down-the-middle as menswear gets.
And therein lies the rub. Fashion is cyclical, and every few years, both light and dark jeans enjoy their moment in the sun.
Medium-wash jeans, by contrast, are basically never the “it” style of the moment. But you know what else they never are?
A bad choice.
A good pair of medium-wash jeans is rugged, versatile and effortlessly masculine. If you intend to have multiple pairs in your closet, I suggest delineating them based on their purpose.
For business-casual looks, opt for skinny fits and darker shades, which tend to look more sophisticated.
For strictly casual looks, you can play with lighter washes and slightly wider fits (though I would never advise straying too far from the Golden Ratio).
But if you only want to own one pair, split the difference and go for a slim pair in a medium wash, which pairs just as well with a blazer and button-down as it does with a t-shirt and a pair of combat boots.
Dress Trousers
A good pair of dress pants can instantly elevate your look.
Throw on a well-fitted polo with a pair of khakis and you’ll look good; swap out the chinos for dress pants and you’ll look sophisticated, worldly and potentially even wealthy (assuming you chose the right shirt and shoes, of course).
Until recently, dress pants were a bit of a devil’s bargain, forcing you to choose between sophistication and comfort. They’ve always looked great, but never felt that great to wear.
Fortunately, today it’s pretty easy to find brands that offer classic styles that incorporate stretch fabrics, giving you all the sophistication of traditional tailoring without having to worry that you’re going to split your pants every time you sit down.
Shorts
Shorts are admittedly one of the tougher pieces to look sharp in. Go too long, and you risk looking like Adam Sandler on his way to… well, anywhere. That guy lives in basketball shorts. (Get your shit together, Sand Man! You’re 60 years old!)
But, go too short, and you risk looking like you forgot your pants entirely and strutted out of the house in your boxers.
From a modern-classic perspective, the key is to find a pair that hues relatively closely to your thighs (without hugging them so closely that your legs look like sausage casings), and hits a couple inches above the knee.
And as with just about every other pair of pants these days, your best bet is probably to find a pair that combines traditional fabrics like cotton with stretch fabrics like spandex or elastane.
That combo combines the comfort of gym shorts with a style that says, “I’m taking the yacht to a neighboring cottage down the Nantucket coast. Lobster rolls, anyone?”
Footwear
White Sneakers
White leather sneakers may be the single greatest style innovation of the last fifty years.
They pair with jeans, chinos, trousers, shorts, sport coats and sweaters. They work on first dates, weekend errands, casual Fridays and even important Monday meetings at a lof of modern office.
If you forced me to build a wardrobe from scratch and only allowed one pair of shoes, I would do two things:
- Choose white leather shoes.
- Judge you vociferously for being such a psychopath—why are you forcing me to make this decision???
Loafers
If white sneakers are the MVP of the modern wardrobe, loafers are the secret weapon.
They occupy a rare middle ground between dress shoes and casual footwear, offering much of the sophistication of the former with nearly all the ease of the latter.
Slip on a pair with jeans, chinos, trousers or even shorts, and you’ll instantly look more polished, refined and put together, without feeling overdressed.
Dress Shoes
You can certainly build a modern wardrobe without proper dress shoes, but not a modern-classic one.
In my opinion, every man should own at least one or two pairs from a reputable brand like Allen Edmonds or Beckett Simonon. Not because you’ll wear them every day, but because when a formal occasion calls for dress shoes, no other style will do.
Weddings, important meetings, fancy date nights, job interviews and special occasions all become easier to navigate when you have a pair of timeless leather shoes waiting in the closet instead of a last-minute problem to solve.
Boots
Me: I should… but I won’t.
Like most things in menswear, the key to getting boots right is avoiding extremes.
Fortunately, that’s easy to do because some of the best styles have already stood the test of time.
Chukkas, Chelseas, dress boots and even clean, understated combat boots have all been worn for decades, and, in all likelihood, will continue to be worn for decades to come.
Why? Because they strike the right balance between rugged masculinity and timeless style.
They’re versatile enough to wear with everything from jeans to tailored trousers, and classic enough to remain relevant year after year.
Chukkas
Chelseas
Combat Boots
Dress Boots
Casual Shoes
As mentioned, a good pair of sneakers can take you damn near anywhere, which means there’s less need for other casual styles.
But two worth keeping in mind are boat/dock shoes, a classic summer-staple that basically hasn’t been improved upon in the past 70 years, and hybrid sneaker/dress shoes, a new innovation that only exists thanks to the smart combination of classic style and modern technology.
Boat shoes remain popular because they do exactly what they’ve always done: offer a comfortable, versatile way to look a little sharper than sneakers without venturing into dress-shoe territory.
Meanwhile, the best hybrids borrow a lot of the visual cues of classic men’s dress shoes (including sharp toe shapes and detailed broguing), but combine them with the comfort and practicality of a basketball shoe.
The result is essentially the entire modern-classic aesthetic boiled down into shoe form, which may explain why I own (and, much to my wife’s chagrin, this is very much not a joke) sevent different pairs of hybrids.
Hybrids
Boat Shoes
Tailoring & Formalwear
Suits
In the world of modern-classic menswear, suits fall into the same category as dress shoes:
You may not wear them that often day-to-day; but when you need them, you need them to look impeccable.
To that end, I recommend owning at least two or three suits in core colors like navy blue and gray. It’s probably a good idea to own one black suit as well, but be warned: black suits are really only appropriate for funerals.
Have them tailored to ensure they fit like a glove, and if you know you’re not likely to wear them very often, keep them in a suit bag in your closet to keep them free from dust.
Ties & Pocket Squares
If you wear a suit to work everyday, then a good rule of thumb is to try and never repeat the same tie in the same work week.
That means you should have at least five ties whose colors complement your core suit colors (which, as noted, should be navy and gray). (One helpful rule of thumb here is to stick with the B’s: blue, black, brown, burgundy.)
If you only wear a tie few times a year, then the recommendation above still holds. But you may also want to just play it by ear, and by a new tie for each occasion.
For instance, if you’ve got a spring wedding coming up and you plan to wear a light gray suit, pairing it with a tie in a lighter or more muted shade is a great way to look modern-classic and seasonally appropriate.
Repeat that move for a few years, and eventually you’ll have a nice little tie collection in a wide variety of colors.
Accessories
Watches
News flash: your watch isn’t for telling time anymore. (Your phone already does that.) It’s for telling other people you have good taste.
In the 21st century, a well-chosen watch communicates style, attention to detail and a certain appreciation for craftsmanship.
When choosing one, stick to the same principles that guide the rest of a modern-classic wardrobe: clean lines, timeless design and understated sophistication.
Your best is to keep the profile relatively slim, which is more sophisticated, more timeless and more versatile than the gaudy, wrist-mounted dinner plates favored by rappers and professional athletes.
Belts
Belts are one of those accessories that are easy to overlook, right up until the moment you realize you’re wearing the wrong one.
Fortunately, building a versatile modern-classic belt collection is pretty easy. Here are the core pieces you need:
One slim leather
belt in black
One slim leather
belt in brown
The two options above will cover you for most formal and business-casual situations. Plus, you could potentially kill two birds with one belt if you opt for a reversible.
One chunky brown
leather belt
One or two neutral
canvas belts
The chunky brown belt is perfect for pairing with jeans and more rugged, casual looks, while the canvas ones give you a warm-weather option. Opt for versatile shades like khaki or grey, which pair well with pretty much any summer shoe.
Sunglasses
Sunglasses are a lot like tattoos: choosing the right one can make you look cooler, while choosing the wrong one can leave you with regrets that last far longer than you’d like.
The good news is that the best styles were figured out decades ago.
Instead of chasing whatever oversized, mirrored, futuristic monstrosity happens to be trending this season, stick with one of the classic frame styles that have been making men look cool for decades.
David Alfons / Unsplash
Oliver Peoples / Instagram
kiuikson / Shutterstock
Bags
Even guys who clearly put some thought and care into their look can see their effort undermined by a bag that’s unworthy of their clothes.
It’s just hard to look cool, confident and worthy of respect when you’re carrying the same black Jansport you’ve had since eighth grade.
With bags, the most important thing to keep in mind is this: leather looks manly.
For business settings, a quality leather briefcase has been the undisputed champion for going on 100 years.
For travel, a leather weekender is perfect for short trips and carry-ons, while a canvas option still looks great if you want something lighter weight.
But if your lifestyle genuinely requires a backpack, leather is really the only option if you want something that looks more refined and masculine, and less like you’re heading to homeroom.
and, finally…
A Quick Note on How Not to F*ck It Up
The core pieces above should give you a pretty good sense of how to assemble a modern-classic wardrobe that nicely threads the needle between classic style and modern sensibilities.
But stocking your closet with modern-classic pieces is one thing; knowing how to put your best face forward is another.
If you’re interested in diving deeper, I’ve put together a free mail series that shows you how to maximize your strengths, downplay any weaknesses, and present your best self to the world.
Enter your email address below to get access today.
