Top 5 Dress Boots for Men

January 3rd, 2014

As you might already know, I’m a former sneakerhead turned footwear collector. While I’ll always have love for a fresh pair of original Js, I have a stronger jones for a well-made pair of leather bottoms (which can be a much more expensive habit, at least in the short term).

Of all the types of footwear I own, I would have to say that dress boots are my favorite category. They’re equal parts dressy and rugged, making them a versatile choice to enhance just about any look, under just about any conditions.

Here I put together a quick recap of my five favorite styles of dress boots, along with some recommendations for good affordable options available now. If you’ve been thinking about a new footwear investment, any one of these styles will be among the most versatile pairs in your rotation, and since so few guys have good dress boots, you are sure to get plenty of compliments on them.

1. Sharp Chelsea Boots

The chelsea is sort of like the loafer of boots. It’s an easy slip-on style with an elastic ankle for flexibility and comfort. My advice is to look for a pair that has a sharp chiseled toebox similar to that of a benchmade pair of oxfords. Avoid anything overly round, chunky or “outdoorsy”. Instead, keep them sharp and lean, and wear them with everything from slim suits to stacked denim.

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2. Sleek Leather Chukka Boots

Desert Boots with crepe soles (like Clarks) are very popular, but they will always look unmistakably casual. I prefer something a little sturdier and luxurious looking with leather (or thin rubber) soles. Again, avoid clunky toes, bulky soles, anything with unnecessary stitching lines, contrast laces/soles, buckles, straps, logos, etc. Keep ’em clean & mean for greatest versatility.

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3. Captoe Lace-Up Boot

It’s hard to fail with a classic captoe lace-up boot, especially in a deep oxblood. As with all versatile footwear, keep them neutral, simple and streamlined and you’ll be wearing them over and over again, no matter the occasion or weather.

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4. Jodhpur Ankle Boot

The Jodhpur is a sexy boot. The ankle strap gives it some attitude, but its simplicity makes it very easy to wear. These are perfect for a night out on the town but work just as well for a day at the office.

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5. Wingtip Brogue

We’ve proven the staying power of the wingtip brogue time and time again. This is a boot that works just as well with suit trousers as it does with jeans, and they’ll only get better with age.

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So what’s your go-to boot style? Use the comments below to share!

Thanks, as always, for reading. 

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America

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