Top 10 Boots to Wear with a Suit

As I’m sure most of you know by now, wearing boots with a suit has not only become acceptable practice but a move favoured by those in the sartorial know. It’s a great way to add a little something extra to your look and break up the monotony that is often associated with wearing a suit. While this may seem like a bold move for a lot of men out there I can assure it isn’t. When your pants fall over the tops of your boot they often end up looking like a heavier dress shoe, something like a brogue to the uninitiated.

There are many different styles of boots out there, and I could probably go 10 deep on different boots to wear with a suit. I think it’s a much more beneficial exercise to look at three categories of boots and break down how to wear the different styles among those categories. As much as I like a heavy winter boot it’s probably not something you’re ever going to throw on with your favourite suit so it seems like a waste of everyone’s time to discuss it.

With that in mind, let’s discuss the top 10 boots to wear with a suit. Within the discussion I’ll let you know the best way to style these and the suits and fabrics that work best with a particular style of suit. At the end of the day, this isn’t rocket surgery and it’s something that should be fun. Have an open mind and you’ll see that this is a fun and interesting way to spice up your suits.

Chelsea Boots:

Chelsea boots are the dressiest of the three categories we’ll be discussing today, which makes them a natural pairing for a suit. Chelsea boots have also seen a resurgence in the style world recently (not that they ever really went anywhere) with them being one of Kanye’s favourite pieces. What makes a Chelsea boot work so well with a suit is that they do tend to look like a dress shoe, which is great for those looking to not shake things up too much.

There are three different styles of Chelsea boots that work well with suits, and they are as follows:

  • Leather with a leather sole: this is going to be the dressiest option of the three and the one that makes the most natural pairing. This style will work well with traditional suits in navy or grey wool, lawyer style. If you’re a fairly buttoned-up guy or work in a stuffy office this is the best option for you;
  • Suede with a crepe sole: this is the style you see most frequently wore in a casual setting but they most certainly will work with a suit too. I would highly recommend going with a suit that’s off the beaten path a little bit; something in a Donegal or bolder plaid fabric;
  • Leather with a rubber sole: this is going to be the one you see most often and will work with pretty much any style of suit. Be sure to purchase a pair that’s relatively slender so they work in concert with your suit; you don’t want something that stands completely apart from the rest of your look.

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Combat Boots:

The idea of combat boots and a suit seems a bit ridiculous off the top, I know. Once you see the right pair on with a suit, however, it will change your tune. The problem with combat boots occurs when you see pairs that are adorned with all sorts of unnecessary accoutrement. If you happen to come across anything that has a strap or some piece that appears out of place, avoid them at all costs. The way you want to see combat boots is as an elevated version of the venerable favourite, Doc Marten’s. With that said, here are three styles of combat boots that are acceptable to wear with a suit (it should be noted that combat boots are best paired with heavier weight, winter suits. I highly recommend you cuff your pants as well. A cuff will provide balance to a heavier boot):

  • Black and simple: this will be the easiest way to wear combat boots with a suit. Find a pair that is inspired by Doc Marten’s but goes the extra step. Think higher quality leather, leather soles, and indiscriminate branding;
  • A little colour: you can occasionally find combat boots in a deep navy or oxblood and doing this is a great way to mix things up. Don’t overdo it with a white pair or anything too bright because then you’re venturing into fop territory; keep things simple;
  • The casual combat boot: try something with a rubber sole that barely fits under the banner of “dressing up.” Sometimes adding a shot of ruggedness to an otherwise refined look is a great way to achieve balance.

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Work Boots:

Work boots, like Chelsea boots, are easier to work with and pair with suits. I say this because now a day’s work boots are actually “work boots;” they don’t have a steel toe and they shouldn’t be worn on a job site. They’re going to be bulkier than a Chelsea boot and slightly less bulky than a combat boot, which means they’re going to work with just about any fabric and style of suit. Blending work wear and fashion is a fun way to dress and is simpler than you think. You can find works boots in all sorts of colours and styles, so here’s three that work best with a suit:

  • Tan coloured: this is a great way to add a shot of colour to your look without standing out too much. These often end up looking like dress shoes to the naked eye as well and is a great way to dip your toe in to the waters instead of diving in head first. Another additional benefit is that these work boots often come with brogueing or wingtip details for a little extra spice;
  • White soled: if you’re willing to really step out try something with a heavy white sole. Style icon Nick Wooster is a master at this. You don’t have to take all of his style cues either, but this one works if you’re willing to take the plunge. This one comes down to confidence.
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  • Oxblood: oxblood work boots are a very handsome and gentlemanly choice. Dark boots will hide imperfections and dirt fairly well too, so if that’s a concern these are a fine option. I think oxblood is best left alone, so don’t try and look for a wingtip oxblood. Let that deep colour do the talking on the boot.

The last boot to round things out to an even 10 here is the cowboy boot. I won’t go in to too much depth here, but suffice it to say the cowboy boot and suit look is not for the faint of heart. If you have the moxie, I say go for it.  

So there you have it, the top 10 boots to wear with a suit. It’s something that may seem intimidating at first but some thought and foresight should dissuade any fears. Try something simple first and work your way up. People will appreciate the effort and take note of your bold new efforts.