Fashion loves to borrow. High heels have a history that includes male wearers. Tailored suits were once firmly associated with men’s wardrobes. Loafers, trench coats, button-down shirts, oversized watches and structured briefcases all have roots in traditional menswear.
And women? We took what worked.
Today, some of the most stylish pieces in a woman’s closet aren’t really “menswear” anymore. They’re simply great clothes.
That’s the interesting thing about fashion. Give it enough time and the rules we once considered absolute start looking rather arbitrary. Who decided a watch needed to be delicate because it was on a woman’s wrist? Why should a briefcase require heels? And when exactly did a blazer become masculine rather than one of the most useful things a woman can own?
So forget the old idea that borrowing from menswear requires adding something sufficiently “feminine” to compensate.
Wear what works.
Here are seven pieces worth borrowing from the boys and making entirely your own.
1. The Oversized Watch
There was a time when women’s watches were expected to be small, delicate and decorative.
Then women discovered the appeal of a substantial watch.
Good decision.
An oversized or traditionally masculine timepiece can look fantastic peeking out from beneath the cuff of a crisp shirt or blazer. It also works with denim, a sweater, a T-shirt or even an evening look if that’s your style.
And please ignore the old rule that a larger watch requires delicate jewelry on the other wrist to reassure everyone that you’re still feminine. Stack bracelets with it. Wear it alone. Mix metals. Pair it with diamonds.
The modern rule is considerably easier: Do you like how it looks? Wear it.
2. The Great Blazer
If there is one menswear-inspired piece every woman should consider owning, this may be it.
A really good blazer can rescue almost anything. Jeans and a T-shirt? Add the blazer. Simple dress? Blazer. Trousers and sneakers? Blazer. Important meeting? You know the answer.
Today’s versions range from sharply tailored and waist-defining to deliberately oversized and relaxed. Neither is inherently more professional. The question is what makes you feel good.
If you’re buying one investment piece, consider a beautifully constructed neutral blazer you’ll wear repeatedly. Then have fun with the others. Try velvet, plaid, color, double-breasted, cropped or oversized.
A blazer doesn’t have to make you look more powerful. But the right one may make you feel that way.
And that’s worth something.
3. The Loafer
Perhaps one of fashion’s greatest gifts from the men’s department is the loafer.
It’s polished without trying too hard, comfortable without looking overly casual and wonderfully indifferent to whether you’re wearing trousers, denim, a skirt or a dress.
Classic penny loafers remain timeless, but the category now includes sleek, chunky, embellished, platform and backless versions. Wear them with socks or don’t. Pair them with a suit or cropped jeans. Put them with a feminine dress precisely because the contrast makes the outfit more interesting.
And unlike the old advice that women need heels to make menswear-inspired pieces work, we respectfully disagree.
The loafer is the point.
4. The White Button-Down
Is there a more useful piece of clothing?
Probably not.
A crisp white shirt can go into the office tucked into trousers and show up at dinner that evening with sleeves rolled and an extra button undone. Wear it oversized over leggings, half-tuck it into jeans, layer it under a sweater, tie it at the waist over a dress, wear it open over a tank or pair it with a pencil skirt.
The magic is in the contrast.
A traditional men’s shirt can look structured, relaxed, sexy, serious or effortlessly cool depending entirely on how you wear it.
And if you’ve ever discovered that the men’s department has the exact oversized white shirt you’ve been trying to find in womenswear?
We won’t tell.
5. The Structured Work Bag
The old leather briefcase has evolved.
Thankfully.
Women still need something that carries a laptop, charger, notebook, glasses, wallet, makeup bag, emergency snack and approximately 14 other things without making us look as though we’re headed to the airport for a three-week expedition.
Today’s best work bags borrow the clean lines and structure of traditional briefcases while acknowledging how women actually live. Look for organization, a protected laptop compartment, comfortable straps, quality hardware and a size that accommodates what you genuinely carry.
Bonus points if it can survive being placed under an airline seat without causing emotional distress.
Leather is beautiful, but it isn’t mandatory. Today’s structured bags come in everything from canvas and nylon to vegan and traditional leather.
The best work bag isn’t the one that looks most executive. It’s the one that makes your life easier while still making you happy when you pick it up.
6. The Trouser
Women have been wearing trousers long enough that calling them menswear feels almost ridiculous. But their tailoring heritage remains part of their appeal.
The modern trouser is particularly good right now because we’ve finally remembered that pants do not have to be painfully tight to look polished. Wide-leg, pleated, high-waisted, relaxed, cropped and tuxedo-inspired styles all offer different ways to play with proportion and shape.
A beautifully cut pair of trousers can be every bit as impactful as a dress and considerably more versatile. Pair them with a silk blouse for work, a fitted T-shirt for something more casual, a sweater in winter or a tank in warmer weather. Add sneakers on Saturday and loafers on Monday.
Great tailoring doesn’t belong to men.
It belongs to whoever is wearing it well.
7. The Unexpected Menswear Piece
This is where it gets fun.
Maybe it’s a trench coat, a tuxedo jacket, an oversized leather bomber, a necktie, a vintage men’s cashmere sweater, a baseball cap, a pinstripe vest, a pair of aviators or, yes, even the fedora from the original version of this story.
The trick isn’t following a complicated set of rules about your face shape, shoulder width or height.
It’s confidence.
Try it on. Look in the mirror. Does it feel like you?
That’s your answer.
The Best Thing We Borrowed From Menswear? Permission.
There was a time when clothes communicated very specific ideas about what women and men were supposed to be. Women have spent generations dismantling those rules.
We wear trousers into boardrooms, sneakers with suits, tuxedo jackets to dinner, men’s watches with evening dresses and oversized shirts with beautiful jewelry. And we don’t need to add a bow, heel or delicate bracelet to reassure anyone that we’re still feminine.
Because personal style gets much more interesting when you stop dressing according to categories and start dressing according to yourself.
So wander into his closet. Or the men’s department. Take the blazer. Try the watch. Buy the loafers. Steal the shirt.
Just remember one thing: Once you make it look that good, you’re probably not giving it back.
Pink POV
Can we officially retire the phrase “dress like a man to succeed like one”?
The most interesting women we know aren’t trying to dress like men. They’re dressing like themselves.
Sometimes that means a beautifully tailored suit and loafers. Sometimes it’s a floral dress and heels. And sometimes it’s his oversized white shirt, your grandmother’s gold bracelet and the watch you bought yourself after your first big promotion.
That’s style.
Borrow from the boys if you want. Just make it unmistakably yours.
