From penny-loafers to combat boots, our picks for the well-heeled gent. By Piera Gelardi & Allison Sparkhul

Continuing our crusade to shod every sole and very soul with an appropriately chic kick, we bring you our second men's shoe roundup for the season‐and this one's for the boys. From all-weather boots to loafers and all leather goods in between, we've got you (and your feet) covered. And ladies, just because these steppers don't come in your size doesn't mean you shouldn't read on. After all, you can't tote him around the tents sporting last season's ankle boot while you're looking hot to trot. So get ready to plunk down some money and pick up some shoes that will surely guarantee a loving and long-lasting relationship (with your man, of course). His mother will love you.

Canvas & Leather

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Acne Jeans High Wedge Boots, $475, available at Acne Studios.
Rag & Bone Dodger Boots, $650, available this fall at Rag & Bone, 104 Christopher Street, NYC.
Heutchy Canvas and Leather Boots, $465, available at Revolve Clothing.

Plaid

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Surface to Air Hunter Check Chukkas, $155, available at Bblessing.
PF Flyers Houndstooth Bob Cousy All-American Lo-Top Sneakers, $80, for availability, go to www.pfflyers.com.
3:33 Plaid Low-Top Sneakers, $198, available at Revolve Clothing.

Penny Loafers

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Opening Ceremony Penny Loafers, $410, available at Opening Ceremony.
Band of Outsiders for Sperry Top-Sider Penny Loafer, $265, available at Apartment No. 9.
Band of Outsiders for Sperry Top-Sider Penny Loafer, $265, available at Apartment No. 9.

Super Snazzy

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Acne Jeans Striking Patent-Leather Shoes, $475, available at Revolve Clothing.
Acne Jeans Fred Patent-Leather Shoes, $475, available at Acne Studios.
Jean-Michel Cazabat Matt Shoes in Gunmetal, $530, available at Revolve Clothing.