38 Lessons: The Ultimate Guide to Men’s Fashion From a Female Perspective

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by  Alice York | Last Updated:  Jul 05, 2020
men's fashion from a female perspective

I am not an adult man. 

What I am is an adult female who’s been interested in style since her preschool years.

I’ll admit, women’s fashion is typically more in my purview.

However, thanks to a well-dressed dad and dapper older brother (if it helps to paint a picture, let me share that he almost always wears a suit to travel…that’s right, a suit on an airplane), I learned early on about fit, fabric, and dress code when it came to menswear.

I’ve also developed opinions of my own on this subject along the way.

Call them preferences or call them lessons, after taking a minute, or, honestly, a day, to pluck these thoughts from the recesses of my mind, I’ve found myself with a style guide of sorts to men’s fashion.

A list of the “what”, 38 to be exact, with some “whys”, for what women want men to wear.

Let me add a disclaimer to this before we get too far ahead. I realize that I don’t speak for all women. I am only one woman on a planet filled with them. 

My penchant for beards and V-neck t-shirts on men, for example, might seem completely unappealing to many (if not most) of my fellow sisters across the globe. But one woman is not an island.

The lion’s share of the below items come from conversations over the years with other ladies in my life—whether in high school hallways or at college parties, over meals, watching TV, or even for planning my wedding—so what you see here isn’t really the ranting and raving of just one broad, but my whole crew of females, past and present.

Enjoy.

Denim

Man sitting in denim and boots

Most of us wear jeans more than any other piece of clothing in our closets. So this wardrobe workhorse ought to be good.

Ditch the dad jeans and find yourself some nice-fitting denim. A dark wash is the most versatile—you can easily dress it up or down and that deep indigo is awfully slimming.

Choose a pair that’s slim (not so tight they look like jeggings), and straight-legged. A cuff can look cool at the bottom but can also make you look shorter, so buyer beware.

If you’re interested in a recommendation, we’re big fans of Mott & Bow. They have a wide range of fabrics and offer almost every style in skinny, slim, or straight fit. And our editor won’t stop telling me how comfortable they are.

But the best thing? You can choose a free “try-on size” pair of jeans which will be sent with your purchase. Then you keep the pair that fits you best, and ship back the other for free.

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The Tuxedo

Attractive man in tuxedo sitting down

Ahh, the tuxedo. Wearing a tux is like being a granted a superpower.

It instantly makes you more than “Average Man”—you look wealthy, deadly, mysterious, powerful. A tuxedo is nothing short of transformative. Try to somehow find a reason to wear one at least every once in a while to experience its effect.

Just like accents, many of us females are suckers for a man in a tux.

Suits

Attractive man in suit sitting down in a nice room

The tailored suit made its way onto the list of 50 Things Every Man Should Own to Win at Life with good reason, and it bears repeating here.

Just like many women are weak-kneed in the presence of a tuxedoed man, a fella in a crisp suit deserves a wolf whistle. A nicely tailored suit projects confidence—it makes you look together, capable, and successful.

In a suit, you look clean and grown-up, like a man familiar with dry cleaning. All of that is attractive.

If you’re on a budget, this is a really well-reviewed option that will get you by until you upgrade to 100% cotton:

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The Leather Jacket

Man leather jacket outside standing

While the whole James Dean/Marlon Brando/leather jacket is a cliché, it’s no accident that some combination of those three things has been cited again and again in anything having to do with men’s fashion.

Let Dean and Brando show you how reckless and sexy this can look if you need further convincing to bite the bullet on this one.

Our picks:

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Last update on 2020-07-09 / Affiliate links / Images from Amazon Product Advertising API

Shoes: Dress

Couple dress shoes and high heels man fashion

Though, admittedly, my husband breaks these fashion commandments from time to time (his “wallet” is a binder clip and many of his shirts have worn out into holes at the elbow), he is on top of his game when it comes to dress shoes.

And what I love most about his dress shoes are that they stay true to his style—you don’t have to speed right from college flip-flops to corporate lawyer/old man territory. He opts for worn-in dress boots, rather than oxfords—they look great and suit him well (and look just as good with jeans, if not better, than with dress pants).

Tip 1: Chestnut-colored leather looks awesome with a blue or navy suit (this was my husband’s wedding look—in my opinion, he looked better than I did that day).

Tip 2: Don’t go too pointy—I think the pointy dress shoe trend is unflattering and over-the-top.

Oh, and if you wear dress shoes for work and you’re on your feet a lot, do yourself a favor and pick up some insoles. We review our favorite ones for reducing heel pain (plantar fasciitis) here.

Shoes: Sneakers

Man sneakers balancing on rail

Sneakerheads, this one’s for you.

I think a cool, well-kept pair of sneakers can be super stylish and a nice leather pair can even sub for dress shoes frequently (dinners, work, dates, etc.).

Cariuma OCA Low

There’s no reason to play coy here—we got these sneakers because they look cool. But after wearing them around for a few months, it became clear that their memory foam insoles make them excellent travel partners.

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For street style, the ‘ugly sneaker’ has been majorly on trend this year. ‘Dad style’ warriors, your time is now.

For more, be sure to check out our list of the 10 Types Of Shoes Every Man Should Own.

Flannel

Middle-aged hipster reading newspaper on leather sofa in barber shop

In my mind, a flannel shirt is masculinity in fabric form.

Maybe it’s growing up with all those Brawny paper towel commercials. Or maybe it’s because I hit my pre-teen years in the 1990s at the height of grunge. Either way, a man in a flannel shirt always looks good to me.

They’re also durable and warm, so flannel is a practical thing to purchase, my ‘90s adolescent fantasies aside.

And it’s hard to go past the classic red:

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“Humor” T-Shirts

Girl with out t-shirt on holding hand up

Shirts with derogatory messages towards women are not okay to purchase (except if they say “FBI: Female Bikini Inspector.” That one’s just funny).

Underwear

Different kinds of men's briefs and socks styles

Buying underwear is a drag.

Even though receiving it from our grandparents at Christmas was the biggest letdown of the year, it was kind of nice having someone just get that done. Now that we’re adults, we need to go buy our own. So go do that.

Clean, grownup underwear on a man is always a nice surprise to see, whether on someone you’re seeing scantily clad for the first time or on a significant other shuffling to the kitchen to make coffee on a weekday morning.

Personally, boxers or boxer briefs top my list—I think briefs give off too much of a little boy vibe (particularly if adorned with any type of superhero design).

MeUndies Boxer Brief

MeUndies makes some of the softest underwear and loungewear I’ve ever tried. While the MicroModal isn’t the greatest material for workouts, the comfort is outstanding.

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We’ve done a couple of underwear reviews you might like to check out:

Plain Tees

Black man in plain white t-shirt smiling

There is nothing better than a man in a white t-shirt.

It’s such a clean, classic look. Throw on an old pair of jeans and some cool kicks (see #6 on this list) and you are perfection.

My husband looks his best in a plain, white V-neck, some dark, button-fly jeans, and his aforementioned worn-in boots. It’s probably safe to say most of you look your best in some variation of that style, too.

The Alstyle’s are a good grab for a crew neck:

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And Next Level for the V:

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Sunglasses

blenders eyewear review featured image model wearing whiskey shiner hexagram sunglasses against sunrise

While I understand the appeal of wraparound sunglasses in a sporting situation, they are a little too Guy Fieri for me otherwise.

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You can never go wrong, however, with Ray-Bans: the Wayfairer, the Clubmaster, the Aviator—these styles have been around forever and suit just about every face. They somehow manage to suit any situation, too: they look equally appropriate at a formal outdoor wedding or at a public pool.

You can buy whatever other brand you prefer, just keep these classic styles and shapes in mind.

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Last update on 2020-07-09 / Affiliate links / Images from Amazon Product Advertising API

Last update on 2020-07-09 / Affiliate links / Images from Amazon Product Advertising API

The Camel Coat

Man in camel coat elegant looking at watch

A nice wool dress coat cleans up literally any outfit you have on underneath.

Ratty t-shirt, sweatpants, and old sneakers? Throw on a camel coat (or any nice wool coat) and you instantly look like a million bucks. It’s like a magic trick.

Like the tuxedo, this is another one of those transformative garments. Invest in a nice one and you’ll have it forever. It will never go out of style. If you don’t want to splurge, places like H&M, Zara, and Uniqlo usually have some good options.

Scarves

Man wearing scarf and carrying weekend bag

Men, it’s okay to wear a scarf.

This sentiment has been quicker to adapt elsewhere than in the United States. I think the consensus is that scarves are too feminine. They’re not. You look good and scarves help keep you warm when it’s cold. Frank Sinatra wore scarves. You’ll be fine.

Socks

green and gold lignes dor pair of thieves socks on model

This is similar to the underwear thing (see #9). Not always so exciting to shop for, but clean, matching socks send a nice message.

Slip on some fancy socks and you look like you have somewhere important to go. A nice pair of navy or black dress socks without holes gives you a little gravitas.

Strideline

While the no-show sock is a bit too high-cut for shoes like loafers, Strideline strikes the right balance between performance and comfort to make great socks for both athletic and casual wear.

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I also like it when you see a little color or pattern peeking out from in between the top of a man’s shoe and the hem of his pants. It shows character, attention to detail, and humor—some very appealing traits.

For socks, a subscription box can be a good idea.

You’ll get a new pair on the monthly which means you can start throwing out those holey ones you’ve been clinging onto since Bush was in the White House. Senior that is.

The Cashmere Sweater

Man in cashmere sweater with beard and tie

Wear a cashmere sweater and two things will happen: we will think you have a great taste and we’ll also start touching you more.

To explain the first part, cashmere is luxurious and if we see you wearing it we’ll think you have a respect for and understanding of quality. That bodes well for you (and us).

As for the second part, cashmere is super soft, so we’ll be getting very close to you when you’ve got that sweater on. That seems like a win-win, right?

Our pick:

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The Cardigan

Man in glasses with cardigan and scarf outside

Speaking of sweaters, I like a man in a cardigan or shawl collar – if you raise an eyebrow to this, do an image search of Paul Newman or Steve McQueen cardigan, and you’ll see what I mean.

Hats: Don’ts

Man in winter hat making silly face

I take a hard line when it comes to hats.

Silly bike messenger-style hats with that teeny brim or any other goofy headgear – fedoras, Cat in the Hat-style hats…they just don’t do it for me. They seem like are just desperate cries for attention. It’s all too forced.

Hats: Dos

Stylish man with beard and beanie and denim jacket

That last one was kind of harsh. And maybe made me seem too anti-hat. I don’t hate all hats. I think a simple wool beanie or a snapback cap are both great options. Less is more.

The Dahlia is really well-reviewed:

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Shorts: Don’ts

Couple, man with capris long shorts at summer festival

Retire the cargo shorts – unless you’re fixing something and need all those pockets for tools, nails, etc.

Also, no man capris. Please.

Shorts: Dos

Man riding bike with brown shorts

By all means, wear shorts when it’s hot. Just keep it simple – classic, plain front; no pleats.

Ties

Man closeup with navy tie and navy suit with white shirt

Fabric matters.

Aim for silk, wool, or knit styles. Avoid polyester. Plain, striped, or dotted styles are usually the best bets, but just as with socks, a whimsical print can be a nice way of showing off your personality and good humor.

Just make sure the situation is appropriate and that that aforementioned humor is in good taste.

Bow-Ties

Man with red bow tie and suit outside with great view

This is a polarizing one.

Many women might find this a turnoff, but I think a man in a bow tie can look pretty darn sharp. I’d recommend keeping the rest of your look simple and slightly modern so the whole look doesn’t get too costume-y.

Henley Shirts

There’s something about a Henley shirt.

This probably dates back to the days when Jared Leto was Jordan Catalano in My So-Called Life (he could wear the hell out of a Henley).

These shirts have a ‘90s appeal—by the end of this list, my strong affinity for the era will be made abundantly clear—and recall the masculinity of #7 on this list: the flannel shirt. I think there is something sexy, too, about those few buttons left unbuttoned.

It’s not so much skin where it’s sleazy or feels clubby; just a glimpse.

Something like this will do the trick:

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Thermal Wear

Man looking in distance with thermal shirt on and sunglasses

I’m doubling up on 1990s fashion here, between the Henley and waffle knit shirt.

Putting daydreams about musicians and actors of that decade to the side for a minute, I think the texture of these are really enticing. And wearing things that are touchable leads to getting touched, which, unless done by a stranger on the subway, is a good thing.

The Briefcase

Young business man running down the street with a briefcase

Let’s step away from grunge-era style for a moment and onto something more professional.

This entry on the list goes hand-in-hand with the well-tailored suit (#3). Both immediately radiate success and style. And a buttery leather workbag only gets better with age: each scuff is like a ring found inside a tree, marking time and experience.

Like the camel dress coat, this is another investment piece. Waxed canvas styles are slightly more rugged and casual but still have work-appropriate polish.

Wallets

Man with suit holding leather wallet

As I mentioned, my husband uses a binder clip in place of a wallet/money clip. Just pinched right from the supply closet at work. But it works for him.

Instead of repurposing office supplies, I’d suggest a simple leather wallet. Good leather is strong and sturdy and will improve with age, just like that nice briefcase you just bought.

Something like:

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Umbrellas

Man running along the beach with umbrella and briefcase

A man with a classic, wood-handled umbrella seems like he has his act together. This man seems prepared for anything.

These aren’t the types of umbrellas you buy during a rainstorm from the drugstore after you’ve already gotten soaked. These are think-ahead umbrellas. This type of forethought makes us feel like we are in good hands.

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Watches

Man with DW watch in park

Your watch shouldn’t be the size of your palm. This looks insane. Less is more. 

Other Accessories

Man with pocket square and polka dot tie

Accessories can be great, but proceed with caution.

Just like the gargantuan watches mentioned above, beware of going overboard. A nice cotton or linen pocket square, simple tie clip, or classic cufflinks will do. Remember this one word: understatement.

Facial Hair

Man with full beard looking into the distance

I love a beard.

Not all women will agree with this. But I think most of us would agree that if you’re going to go for the full beard, don’t live everyday like you’re in the World Beard and Mustache Championships. This falls into the same category as silly hats: it all seems a little insecure and desperate.

Further, if you’re in the bathroom waxing your mustache for the better part of an hour, well, that just seems like time we could’ve been spending catching up on TV or out getting food instead.

Hawaiian Shirts

Man wearing hawaiian shirt and ashamed

Unless you live in Honolulu or own a surf shack in some other tropical locale, Hawaiian shirts just don’t make sense. Or maybe I need to drink more margaritas.

Cut and Fit

Man getting suit tailored

This harkens back to #3 on this list: suits. 

But it also applies in a broader sense to whatever else you put on your body.

Tailoring clothing to fit your body perfectly makes the whole look seem more expensive. If going to a tailor seems like a waste of time and money to you, when you’re out shopping, pay particular attention to the waist and general crotch area of whatever pants you try on, looking for a balance between a vise-like grip and droopy.

Length is also important: an ankle-length pant is experiencing some popularity now and can look sharp on the right guy (and is a great way to show off a colored or patterned sock), but a longer cut with a traditional full or medium break above the cuff is universally flattering—it makes you look taller.

Watch out, too, for sleeve length. Suit jackets/sport coats/blazers should reveal about an inch of your shirt’s cuff—if you go longer, your coat will look too large; any shorter, and can look like you pulled it from your nephew’s closet.

Jewelry

The Steel Shop 12mm leather bracelet with engraving closeup

The whole wearing jewelry thing is tricky – I wear jewelry (although not a lot), so it’s hypocritical for me to say men shouldn’t.

But not every man can pull it off, just like I can’t pull off red hair or tube tops. Professional athletes or musicians look great in jewelry. Accountants might have a harder time making this work.

If you want to stay on the safe side, stick to bracelets and watches.

Swimsuits

Man in swimming trunks with sunglasses

Unless you are Michael Phelps or have the physique of a professional athlete, I’d prefer you stick to swim trunks.

Pajamas

Man on couch in pajamas with coffee

While the style pictured here are not your classic PJs, you know how I feel about waffle knits (see #24)…

The Jean Jacket

Man near water with denim jacket looking away

If you sprinkle in a little bit of The Outsiders, some early Elvis, and James Dean (it all goes back to James Dean) you get the perennially cool jean jacket.

Throw on a plain white tee underneath and some jeans—with the right fit and right shades of denim, a Canadian tuxedo looks classic and cool.

The Trench Coat

Man with trench coat and sunglasses in park

The trench coat = tried and true.

While I prefer the trench in iconic tan cotton—think Bogart in Casablanca—navy or black also get the job done. Like the camel dress coat, this is another piece that cleans up any look, but make sure the fit is right: if it’s too big, you’re going to look like you’re playing dress-up.

This Hart Schaffner Marx is great for the price:

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Shiny Shirts / Suits

Man with shiny shirt and fedora pointing to himself and smiling

Last but certainly not least on the lesson spectrum. No shiny shirts. Or suits.

I can see you just fine without that extra coat of gloss and glitter.


So that’s the list, guys—everything that’s been swirling around in my mind when it comes to what you’re wearing.

Hopefully it’s shed a little light on why that girl gave you that look the last time you were wearing those dad jeans. And you know just the pair we’re talking about: those high-waist, shapeless offenders.

Sorry in advance, fedora wearers. It’s nothing personal.

For more tips, be sure to check out the 50 Things Every Man Should Own to Win at Life.

Over and out.