Many men don’t pay much attention to the style of boots they wear. They go into a shoe store, grab the first pair of boots they see and wear them with everything – often with no regard for whether they actually look good with the outfit. Even if you happen to choose a versatile boot, you’re leaving a lot on the table if you refuse to branch out into other boot styles.

There are several different common styles of men’s boots, and each one offers something different to the wearer. You should own several pairs of boots to go with different kinds of outfits. Here’s what you need to know to wear boots well.

Plain Toe and Brogues Work Well for Formal Wear

Traditionally, boots have been considered a work shoe, and that’s why some men will tell you that you should never wear boots with a formal outfit. But times are changing, and these days it’s fashionable to wear a pair of slim-fitting boots with smart casual, business casual, and business professional looks.

Plain toe boots are a good choice if you’re looking for a boot that will go well with your suits and slacks and keep your feet dry on the way to the office. Plain toe boots don’t have a toe cap, so they’re a sleek and stylish option for pairing with more formal outfits.

Herring Exmoor Tweed Brogue boots

Herring Exmoor Tweed Brogue boots

However, if you want something a bit fancier, you can buy leather toe cap boots with broguing details around the toe cap, or a plain toe boot with broguing. Broguing lends a more formal appearance to a boot, because it suggests the look of a wingtip or brogue dress shoe. Pair your brown or black brogue boots with a navy or black suit or throw on dark brown or black plain toe boots with slacks and a button-down dress shirt for a more business-casual look.

Work Boots Lend a More Rugged Aura to Your Outfits

There are several types of work boots that you can wear for that rugged, masculine, lumbersexual look. Cap toe boots have a visible leather cap over the toe, while moc-toe boots have a moccasin-like seam that runs around the upper part of the boot. Chukka boots are an ankle-length, suede, lace-up boot that is particularly popular in the United Kingdom. And, of course, there are work boots like those made by Timberland, Chippewa, and Red Wing that offers durability for the man who does need to protect his feet during manual labor.

Suede Chukka Desert boots Sutor Mantelassi

Work boots aren’t just for the job site, though. It’s recently become trendy to wear Timberland-style work boots as a fashion statement, but you shouldn’t pair those with slacks or suits. You should probably avoid most types of work boots when styling suits or slacks, with the possible exception of chukka boots, which usually come in light brown colours and can look good with a light grey suit. Instead, pair your Twisted X men’s work boots with raw denim in dark blue or black. Complete the look with a t-shirt under a flannel or a nice pullover sweater. Remember that trousers should come down just to the top of a boot, so cuff your trouser legs to show off the tops of your boots if necessary.

Chelsea Boots Are Good for Understated Elegance

If you’re looking for a casual boot that can nevertheless add elegance and sophistication to your outfit, go with a Chelsea boot. Chelsea boots trace their history back to the days of London’s mod subculture, and they still carry that sense of modern style. They’re a laceless boot with an elastic panel in the side so that you can easily slip them on and off. They go well with jeans and a jacket, but they’re sleek enough to wear into the boardroom, too. Wear your Chelsea boots with dark denim and a jacket, a button-down shirt, or a knitted sweater.

Ted Baker Trallic Leather Chelsea Boots

Ted Baker Trallic Leather Chelsea Boots

Choose Boots in Neutral Colors

Most boots come in black, brown (either dark or light), and navy. Stick with neutral colours for your boots, as they’re more versatile that way – you can wear a pair of dark brown or black boots with just about any outfit, but silver sparkly boots or bright orange boots will require a lot of confidence and a much more developed fashion sense to pull off.

Boots are a versatile and sturdy traditional footwear choice for men but don’t just settle for the first pair of boots you see in the shoe store. Try some different styles – you’ll be surprised at how much a different pair of boots can elevate your look.