Chelsea Boots Outfit Inspiration: 13 Ways to Style this Iconic Boot

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William Barton Avatar by  William Barton | Last Updated:  Nov 16, 2020
Chelsea boots outfit

I get it. 

Sometimes you get stuck in a fashion-rut and end up wearing the same thing every day. It’s not that you don’t have a decent wardrobe. It’s not that you don’t want to put a little effort in. 

A gentle nudge in the right direction with some style inspiration never hurt. 

Chelsea boots are my go-to because they make any outfit look more chic and stylish. Even a simple t-shirt and jeans look better with Chelsea boots. 

So to honor this timeless style classic, I put together five of my favorite Chelsea boot outfits. And make sure you read to the end because I’ve added a ton of other outfit examples from stylish dudes who know how to rock a pair of boots. 

What You’ll Need to Build the Perfect Chelsea Boots Outfit

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I’m going to come right out and say it. If you’ve got a bunk pair of discount dollar-store Chelsea boots, no amount of style-hacks and fashion-tips are going to help you. 

My most recent pick up is the Ace Marks Troy Chelsea boots, and I’m a big fan. Ace Marks manufactures their shoes in boots in Italy, so you can count on top-level craftsmanship. 

Chelsea boots outfit 8

These boots are Blake stitched with a full grain leather upper and a classy leather sole. 

I like the leather sole because it allows me to dress my boots up more than I would with a rubber sole. And because of the slim silhouette, these Ace Marks look at home with a suit. Basically, that allows me to crush it on the dance floor at weddings, and steer away from ubiquitous oxfords. 

Ace Marks Troy Chelsea Boot

The Ace Marks Troy Chelsea Boot is made with premium Italian calf-skin leather and a Blake stitched construction. It's lightweight, creamy-smooth, and has a stunning profile.

Check Best Price How We Style It
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Besides a killer pair of Chelsea boots, you’ll need at least one slim pair of pants, preferably with some taper below the knee. 

Let’s take a minute to talk about what won’t build a stylish outfit:

  • Shorts
  • Relaxed-fit jeans
  • Speedo

Shorts and Chelsea boots don’t mix. The only exception is for pairing Blundstone boots with shorts, but you have to be Australian to pull it off. Or at least have the subtle smell of Vegemite on your breath to make it authentic. 

Relaxed-fit jeans are also a no-no with Chelsea boots. For bulkier jeans, I recommend something like a service boot. A few popular options are the Red Wing Iron Ranger or the Oliver Cabell SB 1.

How to Style Chelsea Boots: 5 Simple and Stellar Outfits

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Chelsea boots are super versatile, which is part of the reason I love them so much. The following five ways are how I end up styling them most often. 

There are plenty of other ways to wear them, whether it’s more formal or more rock-and-roll. To get a glimpse beyond what I’ve posted, scroll down to find how some of my favorite style bloggers crush the look. 

Chelsea Boots with a Suit

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Chelsea boots go with a suit like bread and butter. If you’re going with a tailored suit, make sure your boots are the slimmer style.

In the picture above, I could’ve also gone with brown Chelsea boots and a different shirt, but I like the uncommon pairing of green and black. 

Chelsea boots outfit

I’m wearing the Ace Marks Troy, which is the only Chelsea I own that really pairs well with a suit. I have another pair of Chelsea boots from M.Gemi, and I’m a fan of those too, but the almond toe doesn’t lend itself as well to more formal wear like the Ace Marks Troy. 

Now, I’m not suggesting a green suit is formal—it’s not—but since I don’t have many formal events and I don’t work in an office, I like to have a little fun with the color. 

Black Chelsea Boots with Jeans

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Black shoes and boots are generally more formal, but that doesn’t mean they should always be paired with a suit. A crispy pair of slim jeans looks terrific with polished black Chelsea boots. 

If I’m wearing a pair of black boots, I make sure the rest of my outfit has a little snazziness. Collared shirts, stiffer jeans, shinier watches: these details add up to a clean outfit. When you top it off with a beautiful pair of boots, you look like you’re a man in charge. 

Brown Chelsea Boots with Jeans

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Brown Chelsea boots with jeans is my most common pairing. It’s relaxed and not too serious, but still looks classy and refined. 

I own two pairs of brown Chelsea boots: one is my beater pair that I throw on when I’m heading out on errands or if it’s just rained, and the other I wear out on casual date nights with my wife or when I want to step up my style a little. 

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Here I’m rocking rag + bone jeans with the M.Gemi Dritto Chelsea and an open oxford shirt from Everlane.

If I could only wear one type of outfit for the rest of my life, this would be it. 

And I don’t know who needs to hear this, but it certainly applies to me: if you occasionally go ham on the drinks and end up eating too much pizza and look larger than your normal self, an open oxford over a t-shirt is an excellent way to mask a night (or many nights) of overindulgence. 

Obviously, you’ll look much better with exercise and a solid diet, but I know how it goes. 

Chelsea Boots with Chinos

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Jeans can start to get boring if it’s all you wear. You’d do well to have a nice pair of chinos in your wardrobe. And don’t think that chinos are only for the office or date nights. 

Chinos aren’t very common in American casual dress (at least not compared to jeans), but they definitely don’t look out of place.

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If I’m going for a casual look and want to wear chinos, I keep it more relaxed on top. In the picture above, I’m going with that same open oxford over t-shirt look. I’ve also rolled the chinos a bit to show off some more leather. Quality boots like the Ace Marks Troy become the star of the show, so give them the spotlight. 

Business Casual Chelsea Boots

Chelsea boots

This is a less-common pairing for me, but if you’re looking for a way to rock your Chelseas at the office, I put this outfit together as a suggestion. 

I’ve got the same black chinos as the outfit before, but I’ve styled them a little more office traditional. 

Layering a vest on top of your dress shirt is an excellent way to add some intrigue and the Chelsea boots give a boost of sophistication. 

More Chelsea Boots Outfits Inspiration

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In this more fashion-forward look, Tim’s rocking short inseam pants with black Chelsea boots and a technical fabric overcoat. 

By now, you should be starting to see just how versatile these boots can be. Where my styles are more conventional, you can use these boots to venture into your own style territory.

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A post shared by Tim Dessaint (@timdessaint) on

Here’s another black on black look that adds a touch of class to the military inspired bomber. 

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A post shared by One Dapper Street (@marcelfloruss) on

Feel free to go a little lighter with your look. Suede Chelsea boots are an excellent choice through the warmer months and transition well into fall wardrobes. 

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A post shared by He Spoke Style (@hespokestyle) on

This outfit is put together and clean, and it’s one of those looks that you can throw on in a pinch and still look better than most folks on the street. 

Here are a few more outfits you can peek at for inspiration from our favorite style bloggers:

Have a Favorite?

The 13 outfits above are just the beginning of what you can do with Chelsea boots. If you don’t already have a killer pair, I recommend getting something top quality. A nice set of Chelseas will serve you well through fall, winter, and into spring.

Most of my outfits were styled with the Ace Marks Troy Chelsea boot. Blake stitched, full grain leather, and a sleek silhouette: they’re exactly what I’m looking for in a classier boot. 

Ace Marks Troy Chelsea Boot

The Ace Marks Troy Chelsea Boot is made with premium Italian calf-skin leather and a Blake stitched construction. It's lightweight, creamy-smooth, and has a stunning profile.

Check Best Price How We Style It
If you click this link and make a purchase, we earn a commission at no additional cost to you.

Which of these Chelsea boot outfits fits your personal style? Pop over to our Instagram (@theadultman) to see a few more variations and let me know how you’re rocking Chelseas through our DMs.

FAQs

What shirts go with Chelsea boots?

Chelsea boots can elevate a simple t-shirt, and they also pair well with dress shirts and oxford cloth button downs. So long as your shirt matches your pants (casual or formal), your Chelsea boots should match well.

Are Chelsea boots formal?

Chelsea boots aren’t technically formal boots, though they’ve become more popular in dressy occasions. Now, no one will think twice if you wear Chelsea boots to a formal event. Just keep your Chelseas black with a leather sole and you’ll be fine.

Do you tuck jeans into Chelsea boots?

We don’t recommend tucking jeans into your Chelsea boots. This style is more common for women, and can only be pulled off with a skin-tight taper below the knee. Sophisticated gentlemen don’t typically choose skin tight anything.

What jeans go best with Chelsea boots?

Blue jeans with a taper below the knee go best with Chelsea boots. Choose to cuff the jeans if they have a flatlock stitch, or just let them break along the boot instep.