How 3 It Girls Are Reinventing The Guy-Inspired Look

Yes, we've been seeing athletic, boyish motifs on the runway more than ever, but inspired-by-guys clothing has long been a staple in our wardrobes. From Katharine Hepburn's oversized blazers to Emma Stone's chic red-carpet suits, it's not just about us borrowing from the boys. It's about garnering inspiration from all avenues and genres — even the men's aisle.
So, whether you've been sporting menswear-inspired looks for decades or are just seeking a few choice pieces to add to your style repertoire, look no further than the shopping game of these three style mavens: R29 style director Connie Wang, stylist Heathermary Jackson, and style blogger Vanessa Hong. Take a look at how they're spinning the masculine look to fit their aesthetic, and then pick up a couple pieces for yourself at eBay's Designer Collective. You're going to like the way you look. We guarantee it.
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Her Style MO: comfy, patterned, embellished

The tomboy look goes way, way back — all the way to the ripped jeans, scuffed shoes, and baseball tees you were sporting in fourth grade. It was (and is) a comfy, lived-in look that helped give menswear mass lady — and runway — appeal.

If anyone's an advocate for incorporating boyish elements into feminine apparel, it's our style director Connie Wang. "I hate fashion that gets in the way of being a person, so in that sense I'm a total tomboy," she says. "Anything that doesn't let me walk comfortably, leap over puddles, or make it through the day without developing a charley horse is a no-go."

“But, tomboys love fashion, too, and all the bold patterns, embellishments, and add-ons that come with it," she says. "Just hold the fussiness, please." Ahead, see Wang's take on the new tomboy aesthetic, with her favorite picks of the season.
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"At a glance, this white jumpsuit looks like your typical workman's onesie. However, those embellished pockets are definitely something you won't see at your neighborhood garage.”
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“You could wear this zipped all the way up for a cheeky date look. Or, you can turn it into a high-fashion take on a vest and wear it unzipped, with a pair of patterned shorts and a tank.”
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“These skinny jeans feature a flattering toile print that pairs as lovely with a breezy blouse as it does a leather jacket and band tee.”
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“A perforated faux-leather skirt is actually extremely comfortable (built-in ventilation, anyone?), and the hemline is that magical length where you can wear it to the office and then out to beers with your buddies, afterward.”
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“These overalls are definitely not the ones you remember wearing to Little League. The patchworks are a fun touch that make them feel a little more special.”
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“A pair of neutral-hued plaid pants is a staple of mine. It looks both Ivy League preppy and a bit Manchester punk — two stellar moments in tomboy history.”
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"I don't do plain oxfords anymore. The more patterns, color, and prints, the better!"
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Her Style MO: low-maintenance, effortless, edgy

Stylist Heathermary Jackson is usually behind the scenes, creating covers for Dazed & Confused and Vogue. But, when you stop ogling the glossies and check out the stylist behind the looks, you’ll be equally impressed.

Jackson’s sartorial flair is giving masculine wares — like vintage tuxedo pants — a distinctly feminine touch with stacked-heel brogues or crop tops. “To me, masculine dressing sends a message of effortless style and low-maintenance. Some of my favorites are Winona Ryder in the '90s and Debbie Harry in the '70s."

But, what she really loves is how these pieces "add toughness to each look." That edge gives the wearer a confidence boost, says the stylist. You can shop her picks ahead and see for yourself.
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"My favorite bottoms are a cropped pant. These remind me of Audrey Hepburn in Funny Face — they're the perfect cigarette pant, with a great length and a great cut. Pair them with an oversized tee or a button-down for a perfectly masculine look."
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"I love the boxy, 1960s cut on this dress, which makes it feel more masculine. Plus, the quilting is very unique."
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"This color is really special, and I love the pocket details, thin lapels, and shrunken fit — it reminds me of a schoolboy's uniform jacket."
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"A black belt is a wardrobe staple, and I love the molding of the leather on this. It looks so clean. A men's-style belt toughens any outfit. Wear it with jeans, a button-down, and sandals, and then add a great bag to create a fresh day-to-night look."
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"For a small bag, this boxy clutch has really masculine, clean lines. The lizard print adds something special, and I love the buckle! This would look great worn across the body, with a darker outfit."
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"Despite being a high heel, this shoe has a really masculine vibe thanks to the black leather, black metal hardware, and chunky heel. The heavy heel makes it feel substantial and strong, and the zipper detail and buckles are so interesting and unique."
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"What a great overcoat for fall! This has such a nice 1950s shape, with very simple, clean lines. I like the hidden buttons — they're a unique touch."
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"This ring has a tough, angular feel to it, but it's still beautiful and chic with the gold and emeralds."
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Her Style MO: simple, athletic, classic

One of the most defining traits of menswear is minimalist styling with clean, simple lines. Vanessa Hong, blogger behind The Haute Pursuit, values minimalism above everything else — especially since she spends most of her time living out of her (very stylish) suitcase. Unsurprisingly, she’s pared her wardrobe down to the bare essentials for an aesthetic that’s equal parts athletic and sexy.

“My attitude toward dressing is that your clothes should be simple, impactful, and extremely durable — all of which are important to me as I’m constantly on the go,” she says.

Those qualities are what makes minimalism such a fashion mainstay: It’s classic. It’s clean. And, the contrast of black and white works on everyone. “There’s a certain level of maturity and appreciation of clothing that really comes across when you dress minimally,” says Hong. “And, you’ll always be on trend — today and years from now.” See her long-lasting picks ahead.
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"Leather trackies are an essential in my wardrobe. These are great, because they can be dressed down with sneakers or up with heels, like the ones ahead."
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"I love wearing my jeans in a relaxed outfit, so distressed is key. Siwy makes some of my favorite denim."
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"These are an interesting take on the pointed-toe heel — the three straps give it a caged appearance. I'd wear these with skinny leather pants and a basic tee."
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"Leather shorts are a great item to wear (almost) all year round — they're perfect for summer nights and they're a perfect fall transitional piece. I'd wear this with something structured like a bomber jacket."
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"I love the square shape of the neck — it's very '90s to me. This would look perfect with a pair of leather pants and a simple white sneaker."

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