How To Wear Dress Boots

mens dress boots blue jeans brown boots

Whether you want to break the norm and try out wearing boots with a suit or you just feel like smartening up some relaxed jeans with some classic dress boots, we’re here to guide you through the dos and don’ts of these versatile shoes. 

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How To Wear Men’s Dress Boots with Jeans

Wearing a pair of casual jeans with the more formal dress boot might seem like a tricky thing to achieve but fret not – we’ve compiled a list of the best dress boots to team with denim, along with how to wear them.

Men’s Chukka Boots

Let’s start with the basics. The Chukka boot (also known as the desert boot) was introduced in WWII by British soldier Nathan Clark as a lightweight alternative to the original military boots. Once the war ended, Nathan Clark presented his design to his father, who also happened to run a shoe company, and eventually became the Clarks retailer we all know today.

men chukka boots with jeans
PHOTO CREDIT: Pinterest

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How To Wear Chukka Boots

Chukka boots for men come in a whole range of colours, each one providing a slightly different vibe and style to your outfit. Black desert boots go with most things, so if you’re looking for something that doesn’t require colour coordination, they might be a good choice.

If however, you prefer a warmer look, then a pair of brown chukka boots will help to give a softer finish. Chukka boots for men tend to be made from a light suede, so they’ll give off a more relaxed look than other boots. Match them with a pair of blue jeans and a light top, like a simple white T-shirt, for a classic, flattering style.

mens brown chukka boots jeans
PHOTO CREDIT: Pinterest

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Men’s Chelsea Boots

If you’re looking for dress boots to wear with a suit, then Chelsea boots are a safe option. Their smooth, slip on design gives them an elegant finish that’s perfect for complementing, rather than overpowering, a classic suit. Their close fit also ensures that your feet are kept secure and protected, and makes them perfect insulated dress shoes. 

Men’s Chelsea boots can be paired with an endless array of outfits, smartening up a casual jeans and T-shirt combination, or adding an unconventional twist to a formal suit. Because of their simplicity, they’re generally ideal for a range of looks, and if you choose a pair in a dark brown or black, they’ll go with most colour combinations.

How To Wear Chelsea Boots

While traditionally made from leather, men’s suede Chelsea boots are now a popular design, with the matt texture of the suede helping to tone down the overall look of the boots. Men’s suede boots are therefore a good choice if you’re looking for something to wear with a casual outfit and give a less polished finish.

Of course, leather Chelsea boots are a classic for a reason, and if you want to create a more striking look, then a pair of high shine Chelsea boots will help with this. A pair of black skinny fit jeans with a muted top paired with them will help to emphasise the shine of the boots without creating too much of a contrast.

mens chelsea boots black jeans black chelsea boots
PHOTO CREDIT: Yoka

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Men’s Brogue Boots

The Brogue boot has made a huge comeback over the last decade, and you can go as simple or elaborate with the detailing as you want. A clean black pair of brogue boots in a smooth leather is great for a simple look, or when you want to draw attention to the rest of your outfit.

They’re also secure but because of their lace-up design can be loosened or tightened with ease. This makes them effective winter dress shoes, as you can wear a pair of thick socks without having to squash your feet. So, while there aren’t really men’s dress snow shoes per say, these are probably the closest thing you’re gonna get. 

How To Wear Brogue Boots

There’s plenty of ways to pair brogue boots with jeans, and it’s really up to you how much you want to show off your shoes. Brands like Hudson and Grenson sell the best wingtip boots, giving even simple black brogues an elegant finish. Give your jeans a quick hem at the bottom to help to accentuate your boots, but make sure that you only do this with slim fit or skinny fit jeans, otherwise you’re just gonna end up dealing with loose flappy jeans.

A timeless look is to pair some detailed black brogues boots with some black or navy jeans, and finish off with a bold top. A lot of the time this consists of something like a lumberjack shirt, but anything from a graphic T-shirt to a textured blazer can keep your outfit from looking too simplistic.

black brogue boots for men
PHOTO CREDIT: The Looksmith

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How To Wear Dress Boots with A Suit

We have included the best ways to make your boots suit-worthy. There are so many different types of dress boots out there that it’s not too hard to find a pair to work with formal wear. Boots and suits may seem like a big step for some people so if you’re unsure about the combination, just keep it simple.

Men’s Derby Boots

Very similar to the Brogue boot, but with a slightly smoother finish and slimmer form, the Derby boot is ideal if you’re hoping to create a polished boot and suit combination. As you’re working with dress pants and boots here, you don’t want to go too overboard with contrasts and colours, so it’s best to stick to dark brown or black boots depending on your trousers.

How To Wear Derby Boots

This style of boot is perfect to winter-proof your more formal looks which you will need if you live in a country where you see rain daily (if you’re British you’ll know). Stylish men’s winter dress boots can be difficult to find, but some shiny brown Derby boots paired with a pair of skinny navy jeans, a light mac and a simple white T-shirt.

While we would stick to brown boots during winter, you could be a bit more adventurous with a pair of black leather boots that would work well with a tweed suit. If you wish to stand out even more, then you could also consider warmer tones such as grey or burgundy.

mens blue jeans derby boots-min
PHOTO CREDIT: Pinterest

Men’s Oxford Boots

Every man should own at least one pair of Oxfords in black or brown to wear on formal occasions. Oxford boots generally have neater finishes than brogue or Derby boots, with closed eyelets and smooth, shined leather that gives them a slimmer look. You can get brogue like detailing such as wing tips to help add some subtle interest to the look, but the overall style will still be smoother and more refined.

How To Wear Oxford Boots

Oxford boots are made in a variety of materials that can include canvas, leather, and suede. If you’re looking for something that will work with a formal look, however, then a pair of men’s brown leather boots will work perfectly with some navy trousers, the traditional material keeping things classic and neat, and the colour adding a warm depth to an outfit. 

PHOTO CREDIT: Pinterest

How to Wear Dress Boots

  • Styles – there’s a whole variety from Chelsea, Chukka, Brogue and Derby, there’s a certain style for you
  • Colour – this style traditionally only comes in black, brown and tan
  • Smart – dress boots are perfect for any formal occasion and have become a fashion statement
  • Casual – although they may be called dress boots, you can wear them casually with a nice pair of jeans and a mac
mens black chelsea boots jeans
PHOTO CREDIT: Highsnobiety

On That Note

So there you have it. We have included everything you need to know about the dress boot right from its history through to its modern day use. You should know how various dress boots originated and how they should be worn so that you can too, wear boots confidently and match them with your day or evening attire.

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