Tomboy Vs. Grrrl: 6 Trends Done 12 Ways

Unless you're at a costume party, these days, you rarely come across a person dressed completely in line with one style trope. Even if you qualify yourself as a tomboy, you probably don't see a sea of overalls, Converse, and team jerseys when you open your closet. Likewise, the ladylike dressers among us must own more than silk blouses and A-line skirts. There's always going to be some overlap between the two style philosophies, and if there's any real distinction, it's mostly in their approaches to putting together outfits, not necessarily the items being worn. (We go way into the nerdy nitty-gritty in our book!)
So, what are the differences between tomboy and grrl style? Speaking as a team with folks firmly on both sides: Tomboys favor utility and versatility over fussiness; grrls know exactly what makes them look sleeker, slicker, taller, and trimmer, but enjoy playing around with those proportions, too. What are both groups into? Clothes, obviously, and we've fleshed out six fall trends and how both style types would wear 'em. From traditionally "feminine" pieces, like knee-length skirts, to the "masculine" ones (denim, believe it or not), we've employed a more modern definition to showing how girls like us fool around with fashion, no matter which way we swing.
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PHOTOGRAPHED BY JENS INGVARSSON.
All White
We've spoken before about the benefits of an all-white outfit. When employing this style, make sure you mix in some structure, or you might come out looking like Yanni or Princess Leia.

Tommy Hilfiger Belt; not available online; Tommy Hilfiger Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
It's important not to go too casual, lest you end up looking like the cult in The Leftovers. Find pieces with some volume in shape and heft in fabric, and design elements that are more cheeky than cutesy.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
The boho dress trend is going strong this season, and it's time to let your inner Laura Ingalls Wilder sing. But, avoid the cowboy boots and fringe unless you're headed to a shivaree. Add in modern, classic accents, like ankle boots and a knotted belt to keep things feeling fresh.

Tommy Hilfiger Belt; not available online; Tommy Hilfiger Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
Pleats
The last time both sides might have worn pleats was forcibly through school uniforms, but we think the utilitarian, stiff-but-flowy shape lends itself perfectly to both tomboys and grrrls.

10 Crosby Derek Lam Shirt, not available online; Mango Leather Skirt, $89.99, available soon online; Alexander Wang Shoes. not available online; Milly Skirt, not available online; Alexander Wang Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
A pleated skirt is your version of frill, so keep the rest of your look boxy and boyish. An oxford and overcoat are your typical workday fare, and spectator-shoe inspired booties keep it sleek, but still you.

10 Crosby Derek Lam Shirt, not available online; Mango Leather Skirt, $89.99, available soon online; Manolo Blahnik Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
Pleats are basically just a different sort of ruffle, so double up on this like you would a peplum dress. A pleated top over a pleated skirt is subtle genius.

Milly Skirt, not available online; Alexis Bittar , not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
Denim On Denim
This isn't a new trend, by any means, but the ways people are doing it today feel different than the chambray-shirt-over-skinny-jeans of yore.

Tommy Hilfiger Belt, not available online; Vintage Top; Robert Clergerie Shoes, not available online; Tommy Hilfiger Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
The engineer denim jacket is a new silhouette that tomboys are going to L.O.V.E. this fall. We like wearing it over a half-unbuttoned denim shirt and your colorful jeans from last year.

Tommy Hilfiger Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
A ladylike spin on the all-denim thing is to focus on romantic silhouettes. Soft, off-the-shoulder tops tucked into flared jeans look super pretty, but not prissy.

Tommy Hilfiger Belt, not available online; Vintage Top; Robert Clergerie Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
Layering up casual-ifies a business-professional look. The long-length vest is one of our staples this season, whether paired with an oversized oxford, a shortish shift dress, or even just a T-shirt and jeans.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
A skirt suit doesn't ever have to look retro or boring, if you go for a wild print and quirky design elements, like a longer torso and a high slit. Just make sure your shoulders are on the trim side, to avoid looking too Melanie Griffith in Working Girl.

Brian Atwood Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
Tropical Prints
Summer may be ending, but fruit prints aren't going out of season anytime soon.

Araks Pant, not available online; Kenzo Top, not available online; Kenzo Dress, not available online; H&M Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
You may think that bustiers and tomboys don't mix, but the piece can look surprisingly cool layered over a loose-fit T-shirt and slouchy pants.

Araks Pants, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
Like a good fruit salad, your outfit needs variety. Mix and match your colors, genres, and flora. If it comes in a pre-matched set, even better. The work's done.

Kenzo Top, not available online; Kenzo Dress, not available online; H&M Shoes, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
Knee-Length Skirts
Hemlines are indeed falling, and the just-below-the-knee skirt is the length of the season.

Carven Turtle Neck, not available online; Kaelen Skirt, not available online; Whistle Skirt, not available online; Alexis Bittar , not available online; Maje Clutch, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Tomboy Way:
A body-con pencil skirt might not feel like a tomboy staple, but in a thick, substantial knit (and paired with tough-girl basics like loafers and a leather jacket), it's as effortless as a pair of jeans.

Carven Turtle Neck, not available online; Kaelen Skirt, not available online.
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PHOTOGRAPHED BY JENS INGVARSSON.
The Grrrl Way:
For fancy occasions this season, think about a midi-length skirt in a matching set to bring a bit of edge to a sugar-sweet silhouette.

Whistle Skirt, not available online; Alexis Bittar , not available online; Maje Clutch, not available online.
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