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Wearing Boots with a Suit: 6 Things to Keep in Mind

Wearing boots with a suit is awesome, and not just because “boots with a suit” sounds cool when you chant it. (We won’t judge you if you want to say it out loud a few times.) A pair of boots can bring your suit the kind of swagger that comes from stepping slightly outside of the box — not to mention that it can be a lot more convenient when you’re dressing for cold or wet weather.


To ensure a crisp look when you’re suited and booted, there are a few things to know beforehand. Just ahead, we’ll talk about six must-know tips for any guy rocking boots with a suit.

Boots with a Suit
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  1. Choose the right pair of dressy boots.

When we say “boots with a suit,” we don’t mean any random pair of hiking or work boots you can pull out of your closet. We (usually) mean a pair of men’s dress boots designed to work with formal and semi-formal outfits. Fortunately, tons of awesome dress boots are out there today, in a wide variety of styles and colors.


First, follow the fundamentals of matching footwear color with a suit. If you want to play it safe, that means black boots for a black or charcoal suit and brown boots for most other suit colors. Second, it’s typically best to avoid boots with features that feel too “outdoorsy,” like big lugs on the soles or big chunky laces.


Instead, you’re looking for something with the basic character of a dress shoe. That means leather construction, unobtrusive laces and eyelets (or none at all) and classic styling based on dress shoe designs like Oxford shoes or brogues. Of course, the more casual your suit, the more you can branch out into alternative stylistic choices like desert boots, cowboy boots or even combat boots.


  1. Think about the formality of the occasion.

Even dress boots aren’t right for every situation. If you’re going to a black tie wedding or another event with a highly formal dress code, go with a more standard style of men’s dress shoes like plain-toe Oxfords. These aren’t the kinds of events where you want your fashion choices to rock the boat — and boots will probably rock it.


On the other hand, if you’re wearing a suit to any dressy but less formal event (such as a night out or a friend’s party), boots are almost always acceptable. A semi-formal wedding is also a great chance to bust out your favorite dress boots with a well-cut suit. What about the office? It comes down to knowing your workplace. Very traditional offices like big law firms may frown on it, but many others will find it perfectly fine, or even applaud your sense of style.


boots with suit
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  1. Keep the break of your suit pants in mind.

The “break” in men’s dress pants refers to where the hems end and how wide the leg openings are. Generally, dress boots look best with suit pants that have a shorter, higher break since these pants have an overall slimmer and more streamlined profile. That’s especially important if you go with a sleek style like Chelsea boots, but it’s applicable for basically any type of boots.


You don’t want to go too short, of course. Whatever style of break you’re wearing, the top of the boots generally shouldn’t show when you’re standing or walking. At the same time, full-break pants (the longest style) will often create an unflattering rumpled effect. The best choice is typically half-break or quarter-break suit pants, which offer a solid balance between the extremes.


  1. Think beyond the standard business suit.

Dress boots can definitely work with a standard suit, but they’re often at their best when your suit itself is a little unconventional. If you’ve got something like a tweed or houndstooth suit in your closet, try matching it up with a pair of dress boots. It’s the kind of combo that looks a little offbeat in just the right way, and it’s a great fit for a party or a less formal wedding.


If you’d really like to explore the possibilities of boots with a suit, it’s also worth playing with suit separates in different color combinations. (A pair of medium brown boots is your best friend here — they go with almost everything!) Alternatively, you could wear something that’s not a suit at all. Boots also look excellent with a blazer or sport coat and a pair of chinos.


  1. Shine your boots before you suit up.

Almost all dress boots are made from leather, and that means they’ll look a whole lot better with your suit if you give them a good shine first. Get a basic shoe care kit and spend a little time learning to make your boots look good. It’s not too tough once you learn the fundamentals, and you’ll feel awesome knowing that your boots are at their best.


boots with suits
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Of course, if you chose boots because you’re walking through snow and ice on your way to work, your shine might not look so good by the time you get there. In such cases, it’s worth picking up some leather wipes that you can use to give your shoes a touch-up. Some large transportation centers like train stations even have on-duty shoe shine pros who will get your shoes looking right for a small fee.


  1. Make sure you’re well-accessorized.

Wearing boots with a suit will definitely make your outfit more noticeable, so make sure you’re fresh from head to toe! Adding a few well-chosen accessories is one of the fastest ways to complete your look and make sure your boots are truly working for you.


The right accessories, of course, depend on the look of your boots and suit. First, unless you’ve chosen to go with suspenders, make sure you’ve got a high-quality leather belt that matches the color of your boots. Beyond that, you’ve got tons of options, ranging from staple accessories like a watch or a pocket square to bold statement pieces like a cravat or bolo tie. Try a few things out and discover what feels right!

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