Our definitive guide on how to wear Chelsea boots



So you’ve bought yourself a new pair of Chelsea boots – maybe even one of the best boots of the year – to wear this season? Congratulations, you have made an excellent choice. Not only are Chelsea boots one of the most comfortable styles to slip on due to their elastic side panels and lack of tightening laces, they also have this weird ability to elevate any outfit. You can thank their modern minimalist leather design for that.

If you are new to the style, you might be wondering how exactly to wear Chelsea boots. Can you wear only formal or casual outfits with Chelsea boots, or can you be completely casual? Can you just slip them on with any old pair of jeans, or do they look better with some fit and wash? And with a costume, is that an option?

Good news: Chelsea boots are really versatile. Like, ridiculously. Find your favorite pair and they’ll look just as stylish on a patio drinking frozen margaritas as they’ll make an important presentation in the office. It all comes down to being intentional in the way you style them. And that’s what we’re here to help you understand. So think of this as an introductory lesson on how to wear Chelsea boots, complete with Chelsea boot pattern designs and a handful of outfit examples. Study.

How to choose a Chelsea boot

In summary, the Chelsea boot is a relatively simple shoe. These are just two pieces of leather (or suede) connected by an elastic band and attached to a kind of sole. You would think that would mean that there shouldn’t be as much variation between Chelsea boots. But it just means that every little detail becomes all the more important.

So here are the things you should pay the most attention to: the material, color and shape of the toe. Material side, you are looking for high quality leather or suede. Both are a totally fair game, but keep in mind that leather looks a bit more formal, generally speaking. The color is also up to you, but we’ll keep them neutral, at least for your first pair. Finally, the shape of the toe – aim for a happy medium between pointed and rounded. Think of some kind of egg. Either way, here are two options that fit our criteria perfectly.

Shoe the Bear Dev suede Chelsea boots

Put on the Bear Dev suede chelsea boots.

In recent years, beige suede boots have had their time. Shoe the Bear makes them a solid pair for under $ 200, perfect for those who are just dipping their toes into outfits with Chelsea boots.

Giorgio Armani godet leather chelsea boots

Giorgio Armani Gored Chelsea boots in leather.

For a rockstar look – take your pick – slip on a pair of black leather boots. Like these elegant Chelseas by Giorgio Armani.

Outfit # 1: Weekend Warrior

Are you going for a Saturday full of activities? Wear your Chelsea boots – we’d go for a suede pair here – with a light jacket, a well-fitted tee and dark wash denim jeans for a nice all-day outfit.

Club Monaco aviator jacket

Club Monaco aviator jacket.

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

Everlane Premium Weight Crew

Premium Everlane Weight Crew.

Keep it simple under your jacket with a plain tee. Everlane crafted their Premium-Weight Crew from 6.2 oz cotton in a dense, durable knit that will drape beautifully in layers or on its own.

Uniqlo stretch selvedge slim jeans

Uniqlo Stretch Selvedge Slim Fit jeans.

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

Outfit n ° 2: Adapted and kicked

The opposite of the above, wearing a suit with your Chelsea boots is totally an option. And essentially, the same rules apply to Chelsea boots as any other dress shoe – match your leathers, darker means more formal and, well, don’t think too much about it. As long as you dress confidently, you are golden.

Suitsupply Sienna Dark Gray Check Suit

Suitsupply Sienna Dark Gray Check Suit.

Since they first hit the scene, Suitsupply has been one of our go-to for well-made costumes that don’t break the bank. Their Sienna costume, with its soft, natural shoulders, is one of our favorites. Wear it with black leather Chelseas for a clean and modern look.

Eton Textured Slim Fit Dress Shirt

Eton textured dress shirt.

Of course, you can never go wrong wearing a white 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 in black

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

Schott NYC cowhide motorcycle jacket

Schott NYC cowhide motorcycle jacket.

There is nothing more rock and roll than a black leather jacket, and Schott makes the OG leather jacket.

Comme De Garçons Play Crew-neck T-shirt

Comme De Garçons Play crew neck t-shirt.

A graphic print tee is the perfect place to have a little fun with an otherwise all-black outfit. This Comme de Garçons may be subtle, but the patch of red will definitely stand out in any darkness.

Acne slim-fit stretch denim jeans

Acne slim fit stretch denim jeans.

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

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