Men's Chukkas

Popularized in the mid-20th century, Chukkas continue their long reign of cool. You'll most often find this kind of ankle boot in supple, unstructured leather or suede, with a short run of laces; variations might include a zipper here or there or a crepe rubber sole, as in the desert boot. However they're styled, casual sophistication is assured. (If you can scoop them up on sale, all the better—this is a fashion investment proven to pay long-term dividends.) Shop online or visit our retail store in downtown Pittsburgh.

Men's Chukka Boots


Step up your footwear game with our collection of men's chukka boots. Crafted with meticulous attention to detail and timeless style, our chukkas are designed to make a statement. From the classic mid-brown hues of the Magnanni Malone II to the sleek black elegance of the Magnanni Tacna, our selection offers a range of options to suit any man's taste. And if you're looking for something a little different, the Santoni Dragon Suede Chukka in dark grey or the G. Brown Shoes Koala Chukkas in brown suede and knit are sure to turn heads. Don't miss out on the chance to elevate your style with our premium chukka boots.

Discover the perfect pair that combines quality craftsmanship, enduring style, and a touch of individuality. Don't settle for ordinary when you can step into extraordinary with our collection of men's chukka boots.

Men's Chukkas - Shop By Size

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10.5
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11.5
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8.5
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9.5

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Frequently Asked Questions

What men’s brands does Larrimor’s carry? 

We offer an impressive selection of men’s brands, from  luxury designers and high-quality labels, to a range of custom and made-to-measure men’s clothing. Our collections include designer casual wear for a relaxed look as well as men’s suits, sport jackets and formal wear for more sophisticated settings. Notable brands include: Zegna, Canali, Isaia, Heritage Gold (formerly Hickey Freeman), Eton Shirts, Baldassari, Peter Millar and Vince. Shoe brands include: Magnanni, Santoni and J&M Collection.

Do you offer seasonal collections for men's clothing?

Absolutely! Our men’s collection is updated seasonally with the latest styles and greatest brands to ensure that you stay looking your best all year round. From summer linens to winter woolens, we have you covered. Browse our collection online or visit us at our store located in downtown Pittsburgh.

Does Larrimor’s offer men’s custom clothing? 

Yes. Larrimor’s offers a wide range of made-to-measure and custom clothing for men. From suits, sportcoats, dress shirts, formal wear and wedding suits, to jeans, casual wear and custom men’s shoes, Larrimor’s bespoke menswear selection helps you create the ultimate statement of elegance, confidence and sophistication. Our custom clothing designers include Zegna, Canali, Isaia, Heritage Gold (formerly Hickey Freeman), Oxxford; and Amsterdam based Atelier Munro. 

Does Larrimor’s tailor clothing? 

Yes, Larrimor’s tailors men’s and women’s clothing. We provide on-site complimentary tailoring and alterations on all regularly priced merchandise. Additionally, we offer tailoring and alterations to clothing not purchased at Larrimor’s. The details matter to you and to us. Our expert tailors are dedicated to giving you the best possible fit, every time.

Do you offer accessories for men, like belts or hats?

Yes! At Larrimor’s, we pride ourselves on offering a diverse range of accessories for men, including shoes, belts, hats, wallets, jewelry, socks, sunglasses and more. Complete your look with stylish details from top brands.

Can I get assistance in choosing the right fit or style? 

Yes! Our expert stylists work one-on-one with you to help you with your individual style and appearance by providing expert advice on clothing, accessories and your overall image. They will assist with finding specific items that fit your style and needs whether for everyday or special occasions and events. (optional: Our stylists also offer in-home closet consultations to take inventory of your current wardrobe and offer suggestions on how to mix and match new items with your existing garments. Upon evaluating your closet, if there are any unwanted items, we are happy to coordinate a donation to a local charity and make the delivery for you. After all, it’s our impeccable customer service that sets Larrimor’s apart.)