STYLE

Women Who Rock Menswear Like A Boss (PHOTOS)

07/22/2014 02:14 EDT | Updated 07/23/2014 10:59 EDT

Five years after the release of 2009’s self-titled debut, La Roux is finally – finally – coming out with their follow-up record. Correct, friends: on July 22, Trouble in Paradise officially dropped in North America, which means we’ll get to bask in all sorts of synth-pop glory.

We’ll also get to embark on another few years of style envy. La Roux’s Elly Jackson has set the bar for menswear; proving it’s not a look to be feared or intimidated by. (PSA: Menswear rules, how many times do we need to keep yelling it from our literal rooftop?) And to establish this point, here are 10 other women who give menswear new meaning. That meaning? Everyone can wear it.

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Women Who Rock Menswear

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1. Janelle Monae

Janelle Monae is walking proof that “tomboy style” requires just as much planning and intention as any other look. (Because some of us may have grown up thinking “tomboy” translates to “casual.”) Having previously stated she sticks to her ‘50s tuxedos as a tribute to the uniforms worn by her working-class parents, she also lives her intention to “help redefine what it means to be a woman.” In such, she looks sharp, sleek, and meticulous. Watch yourself, Tom Ford.

2. Alexa Chung

It turns out that even while wading through the mud of Glastonbury, you can still wear a blazer. Enter: Alexa Chung, who’s cultivated an image that’s equal parts fashion boss, equal parts cool/hip older brother. So never fear mixing and matching because that’s what menswear does best. (After all: one man’s flannel shirt is another man’s button-up – either way, they’re both staples.)

3. Cara Delevingne

Even at a garden party, Cara Delevingne reminds us that you don’t need to compromise menswear and/or a tomboy vibe even if surrounded by tea dresses and knee-length skirts. (Not that there’s anything wrong with those.) Overalls, high top sneakers, and a cardigan can still work to create an intentional and even preppy vibe. (If, of course, the prep in question is a cool person whose name can’t be pronounced by Reese Witherspoon.)

4. Kristen Stewart

Kristen Stewart doesn’t get nearly enough credit for her ability not to give a care (“care”? sure) about other people’s style standards. For years, the "Twilight" star has stuck to wearing what’s comfortable – and in the case of a recent photo-op, that was a crop top, high top sneakers, and distressed jeans. Menswear, after all, is a blanket term. And the mix of polished and everyday creates an outfit that’s inherently real.

5. Elly Jackson

Well, what kind of a list would this be without the lead singer of La Roux? (Exactly. A horrible one.) Since embracing the synth-pop sound along with its ‘80s-inspired aesthetic, Jackson has assumed a power role (that voice, seriously) furthered by her affinity for power blazers, prints, and jackets. Because if you didn’t think menswear could be more than tuxedos and button-ups, you (and all of us) have another thing coming.

6. Samira Wiley

Here’s the thing about Samira Wiley: she’s so cool. (And in this photo, she’s with Natasha Lyonne, who is equally so.) But while she rocks just as many dresses as she does gentleman-inspired looks, Wiley will also step out on the red carpet in camouflage print sneakers, a blazer, and skinny jeans. And every time, regardless of outfit, she really does spark the same response: she’s just so cool.

7. Jenna Lyons

J. Crew's head honcho has built an empire from making menswear both a phenomenon and a staple (as opposed to a trend). Through J. Crew, shoppers now have the option of loading up on as many blazers and button-ups as they see fit – to be worn in the same way as the brand’s creative director (sleek and polished), or the opposite. Naturally, Lyons looks all business, always (even in her "Girls" cameo), giving the look yet another interpretation (for everyone with a office dress code).

8. Diane Keaton

It’s as simple as this: thanks to "Annie Hall" and the 1970s, Diane Keaton is the matriarch of the modern menswear trend. Blazers, trousers, and ties, beware: Diane Keaton fans are coming for you, and always will be.

9. Gwen Stefani

Since the mid-‘90s, Gwen Stefani has challenged style norms both successfully and not so much. (Here’s looking at you, cultural misappropriation.) However, since she mid-2000s, she’s gravitated more and more to the “tomboy” side of things, trading in Love Angel Music and Baby (yikes) for camouflage print and oversize flannel. And guess what: it works. There’s a reason those prints have withstood the test of time, and that’s because there’s hardly a person who looks bad in them. (Which is the true test of menswear: can literally any person wear it.)

10. Rita Ora

Rita Ora actually raises an interesting question: with more and more women gravitating towards androgynous style, is “menswear” even that accurate a term? Any woman can wear flannel, or leather, or high tops, or jeans: “menswear” is technically based on the idea that men and women must dress a certain way, and that some sort of style rules still apply. This list actually argues otherwise: these women just have great style. And in the words of Janelle Monae, they’re simply challenging what it means to be and/or look like a woman. You go, girls.