Skip to main content

Your Cart

Close Alternative Icon
EXTENDED: FREE GIFT WITH PURCHASE!
AVAILABLE WHILE SUPPLIES LAST. DETAILS
EXTENDED: ENJOY A FREE GIFT WITH PURCHASE! AVAILABLE ONLY WHILE SUPPLIES LAST. DETAILS
The Best Men's Dress Boots of 2020 The Best Men's Dress Boots of 2020

The Best Men's Dress Boots of 2020

Dress boots are a unique category of footwear that straddle the aesthetic touches of a fine dress shoe with the comfort and functionality of a great pair of boots. When you’re looking to impress, but still need to be able to survive a snowstorm, dress boots are the Swiss army knife of your closet - ready for anything. When making your selection, it’s important to keep four factors in mind.

The Best Men's Dress Boots: The Shadow Grey Suede Cavalier Chelsea

1. Pattern

There are also specific boot designs and patterns that naturally lend themselves to a more formal setting. The Wingtip features a chisel toe, detailed broguing, pinking at the edges, and a toecap medallion, that elevate the model to something much more formal. Chelsea boots like the Cavalier have been paired with suits since Jimi Hendrix and the Rolling Stones, providing some minimalist cool to any look. Classic cap-toe boots also pair equally well with slacks as they do with jeans.

The Best Men's Dress Boots: The Brown Captain Lace-Up

2. High-Quality Leather

The heart of any dress boot is a high-quality leather that shines up nicely and will patina well over time - save rugged leathers for the days when you feel like doing yard work or hiking through the woods. We particularly like pullup leathers like Horween Chromexcel or Thursday Chrome, as seen on the Brown President. These leathers have an undertone that gives them a subtle glow that can be quickly shined up with a little bit of shoe conditioner and a horsehair brush for any occasion. Full grain leathers are another pretty foolproof way of elevating a boot for more formal attire. The soft temper of full grain leathers and their smooth hand feel give them a subtle shine that pairs perfectly with suits or slacks.

The Best Men's Dress Boots: The Cadet Lace-Up

Dress boots also tend to feature leathers with subtle textures and patterns. Leathers that are burnished or finished by hand give a bit of contrast that pairs nicely with more formal occasions. The Walnut Cadet or the Brandy Captain show how a little bit of burnishing can upgrade a lighter leather to something more rich and textured. Oiled suedes are slightly less common in boots, but the subtlety of a fine suede like the Dark Brown Suede Cavalier brings warmth and a bit of nuance to any outfit. If you're really lucky, sometimes you'll find boots made with rare and unique leathers like Shell Cordovan, which has a shine and durability that is legendary.

The Best Men's Dress Boots: The Dark Brown Suede Chelsea Cavalier

3. Design Details

Beyond the leather, look closely for details that differentiate the dress boot from its more common brethren. Subtlety is key to any dress boot. Look for flat wax laces or thin round laces, instead of bulkier leather or kevlar laces. The eyelets and speedhooks should be finished in a way that calls attention to the leather, not to themselves.

Similar to a sports car, you’re also looking for a low profile and sleek lines. This not only differentiates from the utilitarian look of rugged boots, it also ensures your dress boots match with what you’re most likely to be wearing them with - slacks, a suit, or maybe some crisp jeans for a date night. You’ll want the clean, sophisticated last shape that immediately identifies any pair of dress boots and low-profile outsoles that keep the boots from looking bulky.

The Best Men's Dress Boots: The Wingtip

4. Comfort

Finally, don’t forget comfort. Whether it’s a long day at the office or the wedding afterparty, you’ll want to make sure you’re still standing happily afterward. While all of our men’s boots feature supremely comfortable footbeds, the outsole of your dress boots can make a small difference. Rubber outsoles are great for shock absorption, wet weather and daily comfort. However, their grippiness makes them less fun on a dancefloor. If you want something slightly more formal, leather outsoles breathe a little better and are a touch lighter.

Dress boots are the ultimate in versatile footwear. They come in many different permutations, but as long as you get the basics right, it’s hard to go wrong.

The Best Men's Dress Boots for Weddings & Special Occasions

Learn More from Thursday

Have A Question?

No problem! We're always here to help. Just click below for assistance.