How To Wear Dress 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.

Properties of the Chukka Boot

  • 3 eyelets
  • Short shaft which makes it easier to wear with different outfits
  • Calfskin or suede material
  • Rounded toe
men chukka boots with jeans


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


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.

Properties of the Chelsea Boot

  • Close-fitting style
  • Elasticated panels

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


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. 

brown brogue boots for men


Properties of the Brogue Boot

  • Low heel
  • Decorative perforations
  • Toe and heel caps
  • Lace panel

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


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 formalwear. 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.

men's dress boots with suit


Properties of the Derby Boot

  • Open-lacing – The Derby boot has open lacing which means the eyelets are stitched on top of the shoe vamp.
  • Versatility – Because of this particular lacing system, the Derby boot can be adjusted to a tight or loose fit, depending on your preference.

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 black Derby boots paired with a skinny fit navy suit will make you look sophisticated and ready for any important occasion.

While we would stick to men’s black boots you could be a bit more adventurous with a pair of tan grained 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.

black derby boots for men


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 wingtips to help add some subtle interest to the look, but the overall style will still be smoother and more refined.

oxford shoes men


Properties of The Oxford Boot

  • Closed-lacing system – Unlike the Derby boot, the Oxford boot has a closed lacing system, therefore the vamp is sewn on top of the quarters. The difference between closed lacing and open lacing lies primarily in the instep. For those with a high instep, the closed lacing system doesn’t have much room as opposed to open lacing where the eyelet tabs are stitched on top of the vamp rather than under, allowing a roomier instep.
  • Elegance – Between the two lacing systems, closed-lace boots are the most formal option so keep that in mind when you pick your outfit.

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, the traditional material keeping things classic and neat, and the colour adding a warm depth to an outfit. 

men oxford boots with chinos
PHOTO CREDIT: Articles of Style


5 Reasons Why You Should Invest in Cold Weather Dress Boots

There are various reasons why men love wearing dress boots but we’ve listed the main ones.

  • Waterproofing: One reason that would prompt you to switch your thin formal shoes for a chunky sole is probably going to be weather-related. No one wants to turn up to work or to a fancy event with shoes filled with water and a very uncomfortable walk.
  • Durability: Because dress boots usually have a multi-layered sole and inner insulation they do tend to last longer than your average pair of shoes. This means you get to look stylish for longer and get to save part of your wages by not having to replace ruined shoes all the time.
  • Versatility: Dress boots are far more versatile than you’d think and as you read on you will realise how you can dress them up, down and everything in between. We focus particularly on how to wear dress shoes with both casual and smart attire.
  • Protection: With a pair of solidly built boots you will be less likely to feel threatened by cold weather or icy roads. Also, have you ever felt the crushing experience of a weight falling on your foot? If you have then you will regret nothing when wearing dress boots at the time.
  • Style: There is no denying that boots have come a long way from their original strictly utilitarian purposes. Nowadays there is such a wide variation to choose from and with refined options, you simply can’t say it’s difficult to find the right one.
mens black chelsea boots jeans
PHOTO CREDIT: Highsnobiety


What To Look for In A Dress Boot

First things first, let’s focus on what you should really be paying attention to when you’re looking to wear a dress boot. Ideally, you should focus on the exterior, interior and the soles of the boot. There is so much more to the anatomy of a boot, but we want to keep it short and simple, so here are the key things you will want to think of when deciding on what footwear to go for.


The exterior or upper part of dress boots can be made of leather, suede or other more synthetic alternatives. When buying a pair of dress boots always make sure they are of high quality as it will be worth it in the long run. Try and opt for cordovan leather or Church’s as the material will be much more durable.

Remember to regularly polish and shine the outer part of your boots as well so that the leather doesn’t crease over time. If you need some shoe kits, we have you covered.


A boot’s lining is really important for two reasons: comfort and warmth. It is not necessary that your dress boot has a fancy lining, however, if it is fleece lined or has some form of padding then you’ll notice a big difference. Insulated interiors will trap the heat and stop the cold from affecting you which is ideal on those windy days.


The sole of a boot is designed to be long-lasting, although it tends to be the part of the boot that wears out first. The best thing you can do before you start wearing a brand new pair of boots is to work out how often you will be on your feet and walking about so that you can properly take care of its inner and outer components.

How to Wear Dress Boots

When it comes to wearing trousers or jeans over boots, they should typically sit either on or over your shoes for a clean finish. Versatile by nature, most boots can be easily matched with some jeans and a t-shirt for a casual ensemble or elevated with a suit or smart separates.

mens dress shoes
PHOTO CREDIT: Article of Style


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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