Skip to Main Content
chelsea boots outfit 2020
chelsea boots outfit 2020

The Chelsea Boot and Why Everyone Should Own a Pair

February 24th, 2020

The Surprisingly Versatile Chelsea Boot.

One of the things that I admire most about suits is their incredible ability to always look different when worn with a variety of other garments. The same goes for your footwear. When I’m looking to add versatility and a little edge to my look, I almost always reach for a pair of Chelsea boots.

We’ve written pretty extensively about the Chelsea boot and even featured it in our He Spoke Style Boot Guide. With their simple design and construction, the Chelsea boot is a deceptively comfortable boot that has a modern look and can be slipped on and off with ease.

chelsea boots outfit 2020

Weekly business attire can get monotonous. I’m certainly not the type that wants to blend in. From time to time swapping a pair of Chelsea boots, instead of your standard oxford shoe, can give your suited looks the punch it often needs.

chelsea boots outfit 2020chelsea boots outfit 2020

| WEARING |Suitsupply Classic Gray Suit, Black Topcoat, Brooks Brothers Pinstripe Shirt, Navy Paisley Tie, Jack Erwin Black Chelsea boots, White Cotton Pocket Square | PHOTOGRAPHY | by JayPKing

A few easy tips for wearing Chelsea boots with a suit:

1. If you’re wearing a suit for business, be sure that the boot reflects that. A clean and polished pair should always be a top priority. Similarly, make sure your suit trousers are tailored appropriately and aren’t found bunched up or worse, tucked into the boot.

2. Prefer wearing a suit casually? Try experimenting with color and texture. Chelsea boots are also sold in luxurious suede leathers. Suede can look great, but is generally a more causal option that reduces the formality of the look overall.

chelsea boots outfit 2020

3. The Chelsea boot has had a rock star history. Associated with big names, like The Beatles and The Rolling Stones, this edgy boot can transform the look of wearing a suit. Try ditching your normal shirt and tie, for a cashmere turtleneck, and start looking more like your pop icon.

4. Planning a night out? The key is finding the delicate balance between looking dressed up and effortlessly sophisticated. A pair of black Chelsea boots can do this but can also break you out of the office mentality of your typical dress shoe.

chelsea boots outfit 2020

There’s a reason the Chelsea boot has been a staple in men’s wardrobes for decades. When worn with a suit, their versatility is only matched by their one-of-kind style and longevity.

Thanks for reading.

Stylishly Yours,

Steven D. Elliott
He Spoke Style

Photo of Steven Elliott

Steven Elliott

All Posts