How to wear men’s boots

There’s a comfortable Samuel Windsor boot for every occasion

There’s a comfortable boot for every occasion
Image source: Samuel Windsor

Would you wear boots to the office? Offering a sturdier option than traditional shoes, a pair of men’s leather boots combines style with practicality and can be every bit as smart as a pair of Oxfords or Derbys.

From country walks to collecting your OBE from the queen, there really is a boot for every occasion. Here’s our guide to the best of men’s boots and how to wear them.

How to wear Chelsea boots

Good quality Chelsea boots like these Black Chelsea boots from Samuel Windsor feature a Goodyear welted sole

Good quality Chelsea boots feature a Goodyear welted sole
Image source: Black Chelsea boots from Samuel Windsor

Their two piece construction and elasticated gussets put Chelsea boots among the sleekest of men’s footwear options. With a slim profile and rounded toe, they’re an elegant and understated boot that perfectly suits a wide range of applications – think smart evening do or everyday office wear. Alternatively, choose a casual setting for your Chelsea boots by twinning them with a pair of indigo jeans.

If you’re wearing these iconic boots, you should pay attention to the way your trouser breaks. These boots look best with a quarter break or no break, so that the hem of your trouser sits neatly either slightly above or just touching the top of your foot. Go for a straight leg or slim fit too – Chelsea boots are a minimalist look that’s all about creating a clean silhouette.

Searching for a smart casual boot to wear with cords, moleskins or chinos? Try suede Chelsea boots which, with their textured nap, make them a tactile option that’s perfect for a softer ensemble.

How to wear monk boots

Prestige Monk boots from Samuel Windsor

A pair of monks offers a smart casual look with a difference
Image source: Prestige Monk boots from Samuel Windsor

So what if monk shoes were the footwear of choice for the fustier members of the medieval clergy? Today’s monks are at the cutting edge of menswear and look great on sharp-dressing young executives. If you’re a more conventional dresser however, there’s still a monk for you, and that’s the monk boot.

These stylish boots upgrade a casual look to smart casual, and elevate smart casual to smart. Take a pair of jeans which, when you wear them with your chukka boots, are purely casual. Switch to monk boots, add a blazer, and you’re good for a fancy lunch with clients. Similarly, sport a pair of monk boots with dark chinos, turtleneck sweater and velvet jacket, and you’re ready for a swanky evening on the tiles.

How to wear brogue boots

Prestige Country Boot from Samuel Windsor

Wear brogues for a versatile look that pairs perfectly with tweed
Image source: Prestige Country Boot from Samuel Windsor

Classic brogues are uniquely British. From their humble beginnings on the feet of the ghillies who tramped the wet peat bogs of Scotland, they became de rigueur among the aristocratic sporting set of the great estates. They’re now one of the most versatile styles of footwear you can own – country wear for townsfolk and smart boots for country folk. Brogue boots really are for all seasons and most occasions.

Wearing a tweed suit? Brogue boots are a great option – think tan for warm coloured tweeds and black brogues for the cooler tweeds like grey or blue. Alternatively, wear your brogues as part of your casual getup with pair of jeans, fisherman’s jumper, and a car coat. The cherry on top? A wax or cord flat cap.

How to wear Oxford boots

Deep brown Oxford boots from Samuel Windsor go well with dark jeans and grey jacket

Deep brown Oxford boots go well with dark jeans and grey jacket
Image source: Prestige Oxford Boot from Samuel Windsor

Like their country cousins, Oxford boots offer an excellent smart casual option that also looks good as part of a more relaxed ensemble. This take on the traditional Oxford shoe is a preppy look that works beautifully with texture. Think brown Oxford boots, moleskins and a cord jacket.

Going for a more contemporary feel? Oxford boots look great with denim. Try rolling the cuffs up to give your boots the chance to shine. Just never tuck your jeans in.

How to wear work boots

Prestige Cumbria Boot from Samuel Windsor

Rugged work boots are perfect for a country walk
Image source: Prestige Cumbria Boot from Samuel Windsor

Everyone needs a tough pair of boots for everyday adventures. Ideal hardworking footwear, these boots are made for walking, shopping, trips out with the family, cleaning the car, and everything in between. Our top tip: buy a pair with soles that will take you places.

You’ll look great wearing work boots with jeans, cords, moleskins or any other casual trousers. For your top half, think in terms of checked or plaid weekend shirts, as well as tattersall and twill shirts. For warmer weather, slip on a plain t-shirt. A proper old-school sweater is the perfect accompaniment for this casual look – a cable knit Fair Isle, fisherman’s jumper, or nordic sweater will do the trick.

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Posted in How To - Shoes, Leather boots.

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