The Fashion Girl's Guide To Wearing Tailoring & Sportswear

As little girls, many of us were put in pretty sundresses, showered with a shitload of sparkles or shades of pink, and finished off with bows and cutesy accessories. Among those who were given the freedom to run around in trousers, shorts, and jumpers, the majority were probably categorically labeled "tomboy."

In 2016, thankfully, we’re less pigeonholed into having to dress a certain way: Guys can wear skirts without being considered eccentric; girls can do sharp tailoring and sportswear without being described as androgynous. Because really, why should certain clothing be exclusive to one gender or another? Vivienne Westwood once said, “It is not possible for a man to be elegant without a touch of femininity,” and as ever, we salute her foresight and open-mindedness toward fluidity and its influence on fashion.

For a number of seasons, international designer labels, like J.W.Anderson, Wales Bonner, Hood by Air, and Céline, have embraced the agender movement. Skirts and tunics in silk and lace repeatedly crop up during men’s fashion weeks, while stereotypically "masculine" suiting and athletic items have featured countlessly in womenswear collections. Just one look at Alessandro Michele’s transformation at Gucci — and his consolidated, geek-chic vision of ruffled blouses and eccentric patterns for both men and women — and you'll see the way in which both genders are borrowing from each other's wardrobes.

If you haven't yet considered this approach to dressing, let the outfits below be your guiding (styling) light. That way, when Fashion Week commences early next month, and the catwalk continues to blur the line between men's and womenswear, you'll already be a pro.
Photographed by Rebecca Naen.
Vetements sweatshirt, J.W.Anderson turtleneck, Topshop jeans and shoes.
Photographed by Rebecca Naen.
Vetements sweatshirt, J.W.Anderson turtleneck.
Balance out an oversized top, like this long-sleeved sweatshirt from Vetements, with slim-fitting trousers or jeans to even out the proportions. Yes, we know our mothers used to tell us to roll up our sleeves when we were kids, but this season, the longer, the better. Sorry, mom.
Photographed by Rebecca Naen.
Eudon Choi top, Stella McCartney coat.
Photographed by Rebecca Naen.
Eudon Cho top, Zara pants, Stella McCartney coat, Tuza earrings.
Photographed by Rebecca Naen.
Eudon Choi top, Stella McCartney coat, Tuza earrings.
When opting for a crisp shirt and trousers combo, try a softer color, like white, that doesn't feel as structured or stuffy. And, in place of a blazer, make the classic ensemble feel more unique with a tailored denim coat.
Photographed by Rebecca Naen.
Won Hundred jacket, Gucci shorts, Linda Farrow sunglasses.
Photographed by Rebecca Naen.
Won Hundred jacket, BLK Denim top, Gucci shorts, Zara choker.
If you're dabbling in menswear for the first time, a tough, leather biker jacket or bomber is the perfect place to start. If you're already a seasoned vet, be more ambitious, with something unconventional, like basketball shorts.
Photographed by Rebecca Naen.
Tuza choker, Aries top, Craig Green pants.
Photographed by Rebecca Naen.
Aries top.
Delicate jewelry is a subtle, simple way to tone down (and dress up) a look that's overly sporty.
Photographed by Rebecca Naen.
Chloé top, Acne Studios pants, Linda Farrow glasses, Gucci belt, H-Samuel necklace.
Yes, tracksuits are chic. Team a zip-up with tailored trousers to take on 2016's most ubiquitous trend: athleisure. And don't be scared to clash color and pattern, either.
Photographed by Rebecca Naen.
J.W.Anderson top and bottoms, Tonsure vest, Filling Pieces shoes.
Photographed by Rebecca Naen.
J.W.Anderson top and bottoms, Tonsure vest.
Daunted by the idea of a formal suit? Cheat the aesthetic slightly with a tailored longline vest and pinstriped trousers. Here, it's worn with sneakers to dress things down even further, but the look could easily be worn with platforms for a more formal feel.
Photographed by Rebecca Naen.
Matthew Miller suit.
Simplicity is key. Pair a suit with sneakers and a T-shirt for a cool-girl twist on smart casual.
Photographed by Rebecca Naen.
Vetements sweatshirt.
Photographed by Rebecca Naen.
Vetements sweatshirt, Aries shorts, Topshop shoes.
Bored by your weekend wardrobe? Try a hoodie, denim shorts, and slides. Be warned: Everyone you know will want to steal this outfit.

More from Styling Tips

This story was originally published on August 4, 2014. Even though we've all experienced most temperatures, we have selective memory about what they're ...
It's hardly a secret that fall and layering come hand-in-hand. With transitional weather swooping in, and the daily too-hot-too-cold conundrum, we find ...
Remember when Kim Kardashian wore bike shorts and the entire internet collectively freaked out? Well, it seems like she was on to something. Despite the ...
If you're like us, Beauty and the Beast was in heavy VHS rotation when you were a kid. And, if that's the case, there's a good chance you were as besotted ...
Jeans, sweater, booties, repeat. If you don't push yourself beyond this tried-and-true combination, fall dressing can get old...fast. Don't get us wrong...
The switch happened recently: Whereas half-dome breasts achieved via push-up bras were once the shape to mimic, bralettes have made way for more natural ...
Sometimes it can feel like life is just a constant rotation between large plastic bins of clothing — as soon as you're finally getting settled into your ...
(Paid Content) Dressing for your age is a game that's rigged: Try as you may, the outcome is fixed and not often in your favor. One moment women are told ...
Sometimes, looking a certain height is all about perspective
You can switch out your clothes all you want, but you can’t really replicate the way glasses can completely transform you. It’s like presenting an ...
No matter what country you came from or what country you're headed to, first-generation immigrants have a tricky relationship with fashion. What's normal ...
When you're young, you get used to being asked what you want to be when you grow up. But why should that stop when you actually reach adulthood? You don't ...
If you've ever looked at model-street-style roundups and said to yourself, Gosh, I could never afford that, or even, Yeah, but they get all that stuff for ...
Cutouts have always seemed like a really daring thing to wear, especially if you were the kind of woman who wore bras most of the time and didn't consider ...