What To Wear With Five Styles of Boot

Categories Fashion

So you’ve got yourself a brand spanking new pair of boots… now what’s the best thing to wear with them?

Chelsea boots

A slim leather boot that normally comes in a black, the Chelsea’s close fit and absence of laces goes beautifully with the sleek silhouette a suit achieves. The traditional black leather suits with formalwear of any colour, while tan or oxblood are less formal hues that work better with a more relaxed navy blue. The versatile Chelsea boot also partners nicely with chinos and jeans in more casual outfits, too.

Doc Martens

Combat boots with a suit? No thanks. That chunky sole, signature yellow stitching, and high study ankle is a staple of grungier ensembles. Conservative black adapts to any casual combo you want to stick it with — perhaps a graphic tee and/or a leather jacket to round out an edgy look — whereas cherry red adds a pop of colour to otherwise muted ensembles, like your standard light blue jeans and neutral colours on top, plus maybe a complimentary green bomber or M65 jacket to complete an outfit with a military vibe.

Work boots

Any functional-style boot with a similarly thick sole and bulk around the ankles needs to be quarantined from your formalwear, and partnered with slim-cut jeans instead — make sure your trousers aren’t too baggy otherwise the whole shebang just looks oversized. Work boots typically come in brown or tan leather — something like tan Timberlands with skinny dark jeans are a failsafe combo, working well with longline tees and jackets for more contrast between oversized and slim-fit.

Desert boots

A lighter suede boot that typically comes in lighter colours, meaning it’s a go-to during the warmer months to take the formal edge off a suit or add a slightly dressy element to casual wear. The sand-coloured standard contrasts perfectly with blue hues, as a breezy addition to a laid-back navy suit, or a complimentary accompaniment to a slim-cut dark blue jean and a simple white shirt. The increasingly popular brown leather desert boot is similarly versatile.

Other styles

An oxblood cap-toe or a decorative brown brogue are suitable styles for getting suited and booted, as is a Chelsea with a leather strap and buckle around the ankle. The high-ankled cowboy boot or meaty harness boot are both less formal options because they look like they belong on the back of a horse and a motorbike respectively, so keep those two tough, weathered options for a rugged pair of looser-fitting jeans.