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By

Ray A. Smith

Jan. 24, 2018 11:15 a.m. ET



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Ankle boots looked challenging at a Berluti show last year. But they can be styled for a real-world office setting (Berluti, top) or worn casually (Aldo, bottom).

Ankle boots looked challenging at a Berluti show last year. But they can be styled for a real-world office setting (Berluti, top) or worn casually (Aldo, bottom).


Photo:

Gamma-Rapho/Getty Images; F. Martin Ramin/ The Wall Street Journal (2)

Where You’ve Seen Them: Designer

Raf Simons

helped spur interest in ankle boots when he featured a Western-styled version in his debut runway show for Calvin Klein last February.

Timothée Chalamet,

nominated for a best actor Academy Award in “Call Me By Your Name” and singer Harry Styles are among stars recently sporting ankle boots.

Macy’s

called

Chelsea

boots its No. 1 men’s shoe trend for fall 2017.

What’s Their Story: In the late 1830s, English shoemaker

Joseph Sparkes Hall

made the first patented slip-on ankle boot with elastic gussets on the sides, according to the Victoria and Albert Museum in London, and presented the boots to Queen Victoria. In the 1960s, a variation now known as Chelsea boots took off with scenesters who hung around the famed King’s Road in London’s Chelsea—an epicenter of mod fashion—and artists including the Beatles and the Rolling Stones helped make them cool.

Why Your Concern Is Justified: The average guy may find these boots hard to pull off. Remember the ribbing then-presidential contender Marco Rubio got for wearing a pair in 2016? Some fear the look will read “trying too hard.” Done right, you’re a modern Beatle. Not, and you veer into retro

Tom Jones

or, gasp, Austin Powers territory. If you’re going to try ankle boots, you’d better make plans to visit a tailor. Getting the pant length right is crucial to getting ankle boots to look good, especially when it comes to dress pants. You also will need to stock up on over-the-calf socks.

Done wrong, the Chelsea boot look can veer into Austin Powers territory. From left, beware getting pants caught inside the boot; wear long socks to avoid showing bare skin; don’t pair dressy boots with your most casual faded jeans.

Done wrong, the Chelsea boot look can veer into Austin Powers territory. From left, beware getting pants caught inside the boot; wear long socks to avoid showing bare skin; don’t pair dressy boots with your most casual faded jeans.


Photo:

Everett Collection; F. Martin Ramin/ The Wall Street Journal (3)

Why They’re Worth Trying: When you need footwear that has the sleekness of a dress shoe but stands up to winter weather, ankle boots deliver. The alternative, rugged snow boots, are more appropriate for climbing a mountain than the corporate ladder. Plus, “wearing dress shoes day in and day out can get boring,” says Julie Rath, founder and CEO of men’s style consulting firm Rath & Co.

So, How Do I Wear Them?: For ankle-boot beginners, look for a smooth leather or suede in a crisp style without elaborate detailing, says

Ms. Rath.

(If suede feels too casual to wear with a suit, just stick with leather.) Go with a low heel and a standard toe rather than more edgy styles. Ankle boots with rubber or cleat soles are best suited for casual outfits.

Kevin Boone, who works in health-care technology in New York, shows different ways to wear Chelsea boots, styled by Julie Rath of Rath & Co.

Kevin Boone, who works in health-care technology in New York, shows different ways to wear Chelsea boots, styled by Julie Rath of Rath & Co.


Photo:

F. Martin Ramin/ The Wall Street Journal

Pay attention to pant length and width to avoid pants getting caught in the boot. The trick “is to go quite a bit shorter on the pant leg than you normally would so you can see that it’s a boot and not just a laceless shoe,” says Hollywood fashion stylist

Ilaria Urbinati,

who has recently put clients

Tom Hiddleston

and

Joel Edgerton

in suits with ankle boots by Christian Louboutin.

One trick to avoid getting pants stuck in a boot, Ms. Rath says: “Have your pants cut about a half inch longer in back than front.” Sid

Mashburn,

founder of the Atlanta-based men’s retailer of the same name, advises being mindful and adjusting pants legs when necessary. “It just happens,” he says.

Write to Ray A. Smith at ray.smith@wsj.com