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Fall Shoes to Buy Before It’s Boot Season

The styles that’ll get you through October.

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Photo: Mireya Acierto / Getty Images

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What do you wear in between sandal and boot season? It might seem like a tricky thing to figure out, but there are actually plenty of (very different) options. Newer styles like the block heel and updated takes on the classics, like loafers and Mary Janes, are all great for the cooler-but-not-yet-freezing weeks ahead. Plus, they can all be worn with tights once winter arrives.

Below, five styles to rely on until it’s time for thick wool socks.

Photo: Jeffrey Campbell

Block Heels

Block heels have become widely popular in the last few seasons, thanks to brands like Maryam Nassir Zadeh, Mansur Gavriel, and newcomers like Loq. The short, wide heel makes for an easy, everyday shoe, while still adding a bit of height.

What to Buy: Zara Mid-Heel Shoes, $39; Jeffery Campbell Bitsie Heel, $106 (pictured); Miista Taissa Ishida Heel, $240; Ceri Hoover Pump, $295; Loq Villa Heel, $325.

Photo: Matt Bernson


The 2016 loafer is not your grandfather’s shoe. This season’s styles include new iterations with higher heels, different shapes (like the super-popular backless version), and fun prints. A humble suggestion: Go for a pair that incorporates more than one.

What to Buy: H&M Patent Loafers, $34.99; Nine West Buckle Strap Loafers, $89; Matt Bernson Coltrane Slip-Ons, $279 (pictured); Martiniano Saddle Loafers, $488; Gucci Heeled Loafer, $795.

Photo: Loeffler Randall


Also known as brogues, the classic oxford brings a polished edge, making it a perfect office alternative to a pair of not-so-comfortable pumps.

What to Buy: Dr. Marten Antique Temperley Shoe, $115; Vagabond Amina Oxfords, $130; Clarks London Oxford, $140; Everlane Modern Oxford, $175; Loeffler Randall Jasper Oxford, $365 (pictured); Rachel Comey Hayes Bootie, $415.

Photo: Repetto

Mary Jane

The Mary Jane might be the most versatile shoe of the season. It’s evolved way past it’s children’s-shoe roots, with plays on materials, accents (like fur), and higher than high pumps.

What to Buy: Calvin Klein Mary Jane Flats, $99; Repetto Mary Janes, $355 (pictured); Frances Valentine Mary Janes, $395; A.P.C. Victoria Shoes, $435; Prada Patent Mary Jane Pumps, $690.

Photo: Margaux

Ballet Flats

Feel like you’ve exhausted sneakers as the most comfortable shoe? Opt for the dancer-inspired style for a cleaner take without sacrificing ease and comfort.

What to Buy: Zara Lace Up Ballet Flats, $59.99; Margaux Demi Flat, $125 (pictured); J.Crew Collection Drake’s for J.Crew Flats, $128; Josefinas Safari Flat, $179; Repetto Contrast Ballerina Flats, $193.