This site is best viewed in landscape mode.
Listed / 08.20.14

Menswear Inspired Shoes

Toughen up your look with the ten best menswear styled fall shoes!

Why should men have all the fun with their footwear while we’re stuck in heels? Answer: they shouldn’t, and now it’s our turn. Menswear inspired shoes were all over the runways last season, and as the temperature starts to drop (summer, please don’t go!) it’s time to put them to good and stylish use. Oxfords, brogues and combat boots galore; our comprehensive list boasts them all and then some. Peek through to find a pair that adds a touch of tough glamour to all your fall and winter wears.

Best Menswear Inspired Shoes - Rachel Comey Alley Leather Fringe Ankle BootsPin It!

Menswear Inspired Shoes

Rachel Comey Alley Leather Fringe Ankle Boots, $426

Loved For: Wooden heel and fringe detail offer a handcrafted touch to these menswear inspired fall shoes. Nude leather keeps things current, and excellent craftsmanship will keep you impressed.

Buy at: Saks Fifth Avenue, Madewell

  • Stacked heel: 3¾"
  • Padded insole
Price: $426Scoring Strength:
Add to Favorites:
Rachel Comey - Menswear Inspired Shoes:Buy at Saks Fifth AvenueBuy at Madewell
Best Menswear Inspired Shoes - Free People Truemay Lace Up BootPin It!

Menswear Inspired Shoes

Free People Truemay Lace Up Boot, $168

Made For: Ladies looking for a pair of menswear inspired fall shoes that are already distressed with a lived-in look, these lace up Free People exclusives are what you crave! Seriously beat up and with a leather and suede combo, these are the shoes skinny jeans dream of being paired with.

Buy at: Free People

  • Distressed leather
  • Stacked wooden heel
Price: $168Scoring Strength:
Add to Favorites:
Free People - Menswear Inspired Shoes:Buy at Free People
Best Menswear Inspired Shoes - Loeffler Randall Fay OxfordPin It!

Menswear Inspired Shoes

Loeffler Randall Fay Oxford, $350

Best For: Cutouts make these menswear inspired fall oxfords ideal for feeling a bit of breeze, or showing a bit of sock!

Buy at: Nordstrom, Zappos

  • Leather upper, lining and sole
  • Lace-up closure
Price: $350Scoring Strength:
Add to Favorites:
Loeffler Randall - Menswear Inspired Shoes:Buy at NordstromBuy at Zappos
Best Menswear Inspired Shoes - Jenni Kayne Two-Tone Leather OxfordsPin It!

Menswear Inspired Shoes

Jenni Kayne Two-Tone Leather Oxfords, $595

Best For: The metallic panels on these two toned leather oxfords add intrigue to these menswear inspired fall shoes. A streamlined, laceless vamp keeps the look minimalist chic.

Buy at: Saks Fifth Avenue, Shopbop

  • Stacked heel, 1"
  • Padded insole
Price: $595Scoring Strength:
Add to Favorites:
Jenni Kayne - Menswear Inspired Shoes:Buy at Saks Fifth AvenueBuy at Shopbop
Best Menswear Inspired Shoes - Rachel Zoe Raven Cap Toe OxfordsPin It!

Menswear Inspired Shoes

Rachel Zoe Raven Cap Toe Oxfords, $295

Loved For: A metallic toe lends a luxurious look, accentuating the sleek lines of these minimalist oxfords. These are the menswear inspired fall shoes that are definitely made for a woman, and thank goodness!

Buy at: Shopbop, Zappos

  • Inset elastic panels
  • Stacked heel, 1.5"
Price: $295Scoring Strength:
Add to Favorites:
Rachel Zoe - Menswear Inspired Shoes:Buy at ShopbopBuy at Zappos
Best Menswear Inspired Shoes - Joie Lace Up Combat Booties - AsburyPin It!

Menswear Inspired Shoes

Joie Lace Up Combat Booties - Asbury, $415

Made For: Women wanting a tough and kick-ass pair of menswear inspired fall shoes, check out these combat booties that offer all the edge, while still being a feminine favorite.

Buy at: Bloomingdale's, Shopbop

  • Adjustable laces and functional inside zip
  • Feels like 1.5" heel
Price: $415Scoring Strength:
Add to Favorites:
Joie - Menswear Inspired Shoes:Buy at Bloomingdale'sBuy at Shopbop
Best Menswear Inspired Shoes - TOMS ’Brogue’ Wool OxfordsPin It!

Menswear Inspired Shoes

TOMS ’Brogue’ Wool Oxfords, $98

Best For: These tailored wool oxfords are stylish and perfect for chilly days. Suede insole with molded foot bed ensures supreme comfort and support.

Buy at: Nordstrom, Toms

  • Lower collar and 3 eyelets
  • Wool upper
Price: $98Scoring Strength:
Add to Favorites:
Toms - Menswear Inspired Shoes:Buy at NordstromBuy at Toms
Best Menswear Inspired Shoes - Circus by Sam Edelman Farrah Loafer FlatPin It!

Menswear Inspired Shoes

Circus by Sam Edelman Farrah Loafer Flat, $80

Loved For: Looking way more expensive than their $80 price tag. Faux leather upper gets a croc embossed effect for added interest.

Buy at: Zappos, Revolve

  • Faux leather upper with rubber sole
  • Croc embossed detail
Price: $80Scoring Strength:
Add to Favorites:
Circus by Sam Edelman - Menswear Inspired Shoes:Buy at ZapposBuy at Revolve
Best Menswear Inspired Shoes - Vince Newman High Top SneakersPin It!

Menswear Inspired Shoes

Vince Newman High Top Sneakers, $350

Best For: Yay for comfort! These mixed textured high-tops are the ultimate in casual style, and are bound to be the perfect menswear inspired fall shoes to pair with your new favorite track pants or skinny jeans.

Buy at: Shopbop, Nordstrom

  • Mixed texture leather
  • A padded suede collar trims the top line
Price: $350Scoring Strength:
Add to Favorites:
Vince - Menswear Inspired Shoes:Buy at ShopbopBuy at Nordstrom
Best Menswear Inspired Shoes - Tibi Kern Nubuck and Leather Point-Toe BroguesPin It!

Menswear Inspired Shoes

Tibi Kern Nubuck and Leather Point-Toe Brogues, $395

Best For: Black leather with a velvety nubuck panel make these menswear inspired fall shoes ideal to pair with a cropped pant to show ‘em off. A thin sole keeps them from looking too bulky and masculine.

Buy at: Net-A-Porter, Shopbop

  • Velvety nubuck panel
  • A polished lace-up front
Price: $395Scoring Strength:
Add to Favorites:
Tibi - Menswear Inspired Shoes:Buy at Net-A-PorterBuy at Shopbop

Menswear Inspired Shoes

Toughen up your look with the ten best menswear styled fall shoes!

Replay Slideshow
  • Best Menswear Inspired Shoes - Rachel Comey Alley Leather Fringe Ankle Boots
  • Best Menswear Inspired Shoes - Free People Truemay Lace Up Boot
  • Best Menswear Inspired Shoes - Loeffler Randall Fay Oxford
  • Best Menswear Inspired Shoes - Jenni Kayne Two-Tone Leather Oxfords
  • Best Menswear Inspired Shoes - Rachel Zoe Raven Cap Toe Oxfords
  • Best Menswear Inspired Shoes - Joie Lace Up Combat Booties - Asbury
  • Best Menswear Inspired Shoes - TOMS ’Brogue’ Wool Oxfords
  • Best Menswear Inspired Shoes - Circus by Sam Edelman Farrah Loafer Flat
  • Best Menswear Inspired Shoes - Vince Newman High Top Sneakers
  • Best Menswear Inspired Shoes - Tibi Kern Nubuck and Leather Point-Toe Brogues