Tomboy Chic: 15 Menswear-Inspired Shoes to Boost Any Look

Gentlemans Shoes
Photo: Courtesy

A flat, menswear-inspired shoe can elevate any ensemble. You can wear this shoe with all looks because the curved silhouette is extremely flattering. It doesn't cut at your ankle, but just below it—so it elongates your leg while accentuating its tiniest part. Treat this silhouette as you would a basic black flat and wear it with everything.

To prove how versatile this shoe is, here are few outfit ideas:

1. Go minimal with crisp, slightly cropped cigarette pants and a sleeveless mock turtleneck. Depending on whether you want to go for a full-blown menswear look, either leave your tuxedo jacket at home or effortlessly drape it over your shoulders.

2. Balance out a feminine look by pairing it with a menswear-inspired brogue. This look is perfect for your favorite party dress that may be too short to wear to work with heels.

3. Wear a menswear-inspired lace-up as a counterpart to the ever-popular midi skirt. The silhouette of a midi is fun and playful, which calls for a more serious, structured shoe.

4. Team your lace-ups with a sleek pencil skirt and a fine-knit sweater and create a monochrome ensemble. The idea here is to keep your look as clean cut as possible. Jewelry-wise, add a few skinny bangles and you're done.

5. To create a cool and comfortable weekend outfit, cuff your boyfriend jeans and wear the shoe sans socks. Carry an oversize pouch for an effortless look.

If the silhouette feels a little too borrowed-from-the-boys for you, seek out styles with eye-catching elements like metallic detailing and color blocking.

To add a dose of tomboy chic to your style, shop 15 pairs of menswear-inspired shoes in our gallery.

01 of 10

Gentleman's Club

Gentlemans Shoes
Greg Marino

This shoe is no one-trick pony: You may have worn the menswear mainstays sans socks with rolled-up boyfriend jeans, but lace-ups and loafers also put a playful spin on dressier looks. Here are a few to try on.

SHOP IT
Clockwise from top: Paul Smith, $595, paulsmith.com for stores; Boden, $148, bodenusa.com; Rag amp Bone, $475, nordstrom.com for stores; the Office of Angela Scott, $550, theofficeofangelascott.com; Kate Spade Saturday, $160, saturday.com

02 of 10

Vince

Gentlemans Shoes
Courtesy

$425; shopbop.com

03 of 10

Zimmermann

Gentlemans Shoes
Courtesy

$495; shopbop.com

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The Office of Angela Scott

Gentlemans Shoes
Courtesy

$495; neimanmarcus.com

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Giorgio Armani

Gentlemans Shoes
Courtesy

$845; neimanmarcus.com

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Charles Keith

Gentlemans Shoes
Courtesy

$79; charleskeith.com

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J.Crew

Gentlemans Shoes
Courtesy

$268; jcrew.com

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Kate Spade New York

Gentlemans Shoes
Courtesy

$278; shopbop.com

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Silence + Noise

Gentlemans Shoes
Courtesy

$89; urbanoutfitters.com

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Zara

Gentlemans Shoes
Courtesy

$100; zara.com

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