From Monkstraps to Chukkas: A Men’s Shoe Style Guide

Oxfords. Loafers. Chukkas. Chances are you’ve heard of these, but do you really know what they are? If you’ve misused or misattributed these terms (and others) a time or two, fret not. We’re here to break down some popular men’s shoes styles – from what they’re called to how to recognize the subtle differences that make them what they are. Read on.

Men's Shoe Style Guide


1. Monkstrap: Boasting a buckled strap or two in lieu of laces, GQ calls this shoe “the dressiest of all men’s shoes.” Not necessarily for the faint of heart, monkstraps make a major statement. Pair with a suit, or if you’re the adventurous type, turn heads in cuffed jeans or cargo pants.

2. Oxford: Also referred to as the balmoral, oxfords are the quintessential day-to-night dress shoe. Whether plain or wing-tipped and brogued (as above), this is your go-to for work and other occasions when a bit of polish is a plus. Conventional wisdom says they’re best with formal looks, but one peep at these fashionably adventurous men proves that oxfords can work with everything from dress pants to shorts.

3. Chelsea boot: This style dates back to the equestrian Victorian era, but its modern iterations are on-trend today. Very British in their look (Chelsea boots were big when Mod rolled around), these boots work well with tailored pants, slim-cut suits, and straight-leg jeans.

4. Derby: Also known as a Gibson or a blucher, derby shoes are often mistaken for oxfords. But there’s one crucial difference  – the lacing is sewn outside of the shoe on the derby, leaving a visible flap. This more noticeable lacing style makes derbys a bit more casual than oxfords, though they still may feature cap-toes (as above), wing tips, broguing, and other detailing. From tailored dress pants to crisp khakis and well-worn jeans, this versatile shoe is your throw-on-and-go, heavy-rotation style.

5. Chukka: These ankle-length turf boots are identifiable by the two to three pairs of eyelets they typically have for lacing. Often made in leather or suede, these boots have a casual – but very put-together – vibe that works well with both jeans and khakis. The shape is fairly safe and classic, so if you’re looking to make a statement, opt for a bright color.

6. Loafer: Made in a myriad of styles and materials, loafers are an ultra-versatile choice. Thicker soles and penny slots, as above, are more casual, while tassels and high-shine leather skew more formal. Wear these with everything from a T-shirt and jeans (cuffed with no socks if you’re looking to make waves) to a dapper suit with dress socks.

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By Chrissy Makkas, Staff Writer

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August 14, 2013