The Best Chelsea Boots to Wear With Everything

Preppy style has gotten a little pretentious over the years. So Sperry recently launched a campaign to redefine preppy style. I actually mentioned it in a previous post you can read here. It’s awesome that Sperry is rolling out shoes that are still timeless. But they’re less stuffy than you’d associate with preppy style. In this post, I’ll share the best Chelsea boots to wear with everything.

I am a huge boot guy, especially Chelsea boots. Instead of wearing tennis shoes, I’ll throw on a pair of boots. You’ll look like you tried even if you rolled out of bed and literally slipped the boots on. I love Chelsea boots because they’re sleek enough to wear with a suit but can also dress up your toughest jeans. Plus they’re lighter than most boots. So they’re a shoe that you’ll wear year-round.

If you’ve never worn Chelsea boots before, I’d recommend testing the waters with a suede pair. But the best Chelsea boots to wear with everything would be a black leather Chelsea boot. Sperry sent me a pair of their Gold Cup Exeter Chelsea boots to style. Because the shoes are such a classic, I wanted to pair them with pieces that were as timeless. People associate Sperry with preppy styles. That’s why I wanted to style an outfit that was a little more rebellious. There’s nothing more classic than a button-down, leather jacket, and Chelsea boots.  

I already own a pair of Chelsea boots. I’m not going to lie, they’re little uncomfortable. When I slipped on this pair, they were super comfortable right out of the box. They’re lined with lambskin so these are a pair of shoes you can stay in all day long. Click the links below to shop the post!

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