Of all the types of footwear, dress boots are the favorite category for many men. They are equal parts dressy and rugged, making them a versatile choice to enhance just about any look, under just about any condition.

Here is a quick recap of 5 favorite styles of dress boots, along with some recommendations for good affordable options. If you have been thinking about a new footwear investment, any one of these styles will be among the most versatile pairs in your rotation, and because so few guys have good dress boots, you’re sure to get plenty of compliments on them.


The Chelsea is sort of like the loafer of boots. It is an easy slip-on style with an elastic ankle for comfort and flexibility. Look for a pair that has a sharp chiseled toe box similar to that of a bench made 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.


Desert Boots with crepe soles are very popular, but they will always look clearly casual. Again, avoid bulky soles, clunky toes, anything with unnecessary stitching lines, contrast laces or soles, logos, straps, buckles, etc. Keep them clean and mean for greatest versatility.


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


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


Wingtip brogue has proven the staying power time and time again. It’s a boot that works just as well with suit trousers as it does with jeans, and they will only get better with age.