3 Essential Men’s Boots and How to Wear Them

Combining boots and a suit isn’t all that hard – put on a suit, add the boots – but it does require some finesse to get down to a T. Figuring out which boots look best with which suits does take some careful consideration in order to avoid making mistakes like putting on a pair of hulking technical boots under your double-breasted, soft-shouldered suit. That being said, here are the three essential silhouettes everyone should include in their wardrobe, and what you need to know about wearing them with your best suit.

The Chelsea Boot

Chelsea boots

You can’t go wrong with the Chelsea boot. Named after the area in central London where every kid wore them in the early sixties, as far as style and comfort mens boots go, they’re right at the top. They go amazingly well with slim pants, and besides that, there aren’t any other requirements for wearing them. Pants that feature a narrow leg opening and a light break (or none at all) are ideal to wear with Chelsea boots. These two subtle, but crucial details will make you look leaner and taller.

Combat Boots

combat boots

Combat boots are always shiny, always black, and always ready to add an extra layer of toughness to your most refined suit. They’re boots you can get away with wearing almost everywhere, and contrary to popular belief, they’re more similar to dress shoes than field-ready boots. The only difference is, they’re higher than dress boots, and they’re not too narrow and not too thin-soled, so they go incredibly well with a cuffed hem.

Chukka Boots


As far as leather style and comfort mens boots go, chukkas are one of the best to do it. Their smooth surface and subtle stitching make them easily wearable and elegant. They originate from Polo, where chukka is a period in the game. However, the inspiration for the silhouette of the boot comes from the desert boots used by British soldiers who fought in Africa during World War Two. You can pair them with a chino suit.


These are the three basic men’s boots that every man should include in their wardrobe. Once you get these staples, you can go on and experiment with other boots. There are many different models and variations of the Chelsea, combat and chukka boots, so you can pick between models that although look similar, there are subtle differences that can make on model fit you better than the other.