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Mr. Ocean

Chelsea Boots Forever

No matter how much my style evolves over the years, the Chelsea boot always remains of my favourite pieces of footwear. There’s nothing I’d rather wear with a fitted pair of jeans and if you find the right pair, they’re no less comfy than your fave pair of sneakers if you buy the right pair. Really, read on.

Most Chelsea boots come in suede or leather and I’ve seen a dozen colours and while it’s nice to have a pair in black or a chestnut brown or even a navy suede, make sure to get a pale tan shade first as they work perfectly with every colour of denim. Now here’s the simple secret to a great Chelsea, the gum sole. This is an absolute, unequivocal no discussion for me. I do not want a dress shoe style boot click clacking down the sidewalk or hallway. I want thick, quiet and soft. The last thing to keep in mind is to find a pair with height as the shorter ankle style look allows your pant leg to pop off and actually find itself inside the boot. Not a good look, bro.

Here are a few of my favourites to shop.


The Cadillac of Chelseas. I have a pair from Mr Porter that have lasted years and are due for another clean up at the shoemaker.


Just can’t beat the price of these beauties. Almost a carbon copy of the CP’s and 1/5 the price. There’s a few pairs on sale now for under $100…


At a price in the middle of the others, Oro has some killer boots in some unique styles. The “Crepe” sole Chelseas are a great option.

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I am a Canadian-based entrepreneur, content creator, creative director, founder of the Loft 109 studio, co-founder of Platform Media & Management, founder + lead designer of Nightswim + aspiring realtor. With an unquenchable affinity for style, culture, and all things within the realm of design, I try to apply my experiences + skillset to nurture my own and my client’s projects. I am a dog dad to Frenchies named Junior, Fred + Elmer, a sucker for all things automotive and a longtime fitness + sport enthusiast.