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Our Definitive Guide on How To Wear Chelsea Boots

Male wearing Brown Leather Chelsea Boots, legs crossed at the knee, sitting in a sun room.

So you bought yourself a new pair of Chelsea boots — maybe even one of the best boots of the year — to wear out and about this season? Congratulations, you’ve made a great choice. Not only are Chelsea boots one of the more comfortable styles to slip into due to their elastic side panels and lack of constricting laces, but they’ve also got this uncanny ability to elevate any outfit. You can thank their modern minimalist leather design for that.

If you’re new to the style, you may be wondering how to wear Chelsea boots exactly. Can you only wear formal or business casual outfits with Chelsea boots, or can you go full casual? Can you just throw them on with any old pair of jeans, or do they look best with a certain cut and wash? How about with a suit, is that an option?

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Good news: Chelsea boots are really quite versatile. Like, ridiculously so. Find your favorite pair and they’ll look just as stylish on a patio drinking frozen margaritas as they will delivering an important presentation at the office. It all comes down to being intentional in how you style them. And that’s what we’re here to help you figure out. So consider this an intro course on how to wear Chelsea boots, complete with model Chelsea boot styles and a handful of outfit examples. Study up.

How to Choose A Chelsea Boot

When you boil it down, the Chelsea boot is a relatively straightforward shoe. It’s just two pieces of leather (or suede) connected by a band of elastic and attached to a sole of some sort. You’d think that would mean that there shouldn’t be that much variation between Chelsea boots. But that just means that every little detail becomes that much more important.

So here are the things you should be paying most attention to: Material, color, and the shape of the toe. In terms of material, you’re looking for high quality leather or suede. Both are totally fair game, though keep in mind that leather leans a little more formal, generally speaking. Color is also up to you, but we’d keep them neutral, at least for your first pair. Finally, the shape of the toe — shoot for a happy middle ground between pointy and rounded. Think kind of egg-shaped. Anyway, here are two options that neatly fit our criteria.

Shoe the Bear Dev Suede Chelsea Boots

Shoe the Bear Dev Suede Chelsea Boots.

Over the past few years, tan suede boots have had quite the moment. Shoe the Bear makes a solid pair for under $200, perfect for those just dipping their toes into wearing outfits with Chelsea boots.

Giorgio Armani Gored Leather Chelsea Boot

Giorgio Armani Gored Leather Chelsea Boot.

For a look worthy of a rockstar — take your pick who — slip on a pair of black leather boots. Like these sleek Chelseas by Giorgio Armani.

Outfit #1: Weekend Warrior

Headed out for a Saturday packed full of activities? Wear your Chelsea boots — we’d go for a suede pair here — with a lightweight jacket, a well-tailored tee, and dark wash denim jeans for a handsome all-day outfit.

Club Monaco Bomber Jacket

Club Monaco Bomber Jacket.

Inspired by a classic military design, the bomber jacket marries form and function like no other. Look at this Club Monaco version: it’s clean and modern, cut for comfort and style, and will look great with a fresh pair of Chelseas.

Everlane Premium-Weight Crew

Everlane Premium-Weight Crew.

Keep things simple underneath your jacket with a solid t-shirt. Everlane’s crafted their Premium-Weight Crew from a 6.2-oz cotton in a dense, durable knit that’ll drape beautifully layered or on its own.

Uniqlo Stretch Selvedge Slim Fit Jeans

Uniqlo Stretch Selvedge Slim Fit Jeans.

Uniqlo makes some of the best, most affordable selvedge jeans around, which makes them a no brainer for everyday weekend wear.

Outfit #2: Suited and Booted

On the opposite end of the spectrum from the above, wearing a suit with your Chelsea boots is totally an option. And essentially, the same rules apply to Chelsea boots as they do to any other dress shoe — match your leathers, darker means more formal and, well, don’t overthink it. As long as you’re dressing with confidence, you’re golden.

Suitsupply Dark Grey Check Sienna Suit

Suitsupply Dark Grey Check Sienna Suit.

Since they came on the scene, Suitsupply has been one of our go-tos for well-made suits that don’t break the bank. Their Sienna suit, with its soft natural shoulder, is a favorite of ours. Wear it with a black leather Chelseas for a clean, modern look.

Eton Textured Slim Fit Dress Shirt

Eton Textured Slim Fit Dress Shirt.

Sure, you can never go wrong wearing a white dress shirt under your suit. But we say, why not be bold and wear something like this Eton shirt with more texture and pattern?

Outfit #3: All Black Everything

When Chelsea boots first came back into fashion in the ‘60s, they were popular in the mod scene — musicians like the Rolling Stones and Beatles loved them. Channel those retro rocker vibes by wearing them with an outfit that’s all black head to toe. As for which pair to wear, you can keep the dark shade going by going black leather, or wear light suede Chelseas for a bit of contrast

Schott NYC Cowhide Motorcycle Jacket

Schott NYC Cowhide Motorcycle Jacket.

There’s nothing more rock and roll than a black leather jacket, and Schott makes the O.G. leather jacket out there.

Comme De Garcons Play Crewneck T-Shirt

Comme De Garcons Play Crewneck T-Shirt.

A graphic printed tee is the perfect spot to have a little fun with an otherwise all-black outfit. This Comme de Garcons may be subtle, but the spot of red will definitely stand out from all the darkness.

Acne Slim-Fit Stretch-Denim Jeans

Acne Slim-Fit Stretch-Denim Jeans.

Elevated essentials are the name of the game when it comes to Acne Studios and this pair of black denim jeans are no exception.

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