How to Style Chelsea Boots for F/W

ways to style chelsea boots for fall and winter puffer coat brown coat brown sweater jeans leggings

If you’re searching for a staple pair of boots to use through fall and winter, I highly recommend investing in a pair of Chelsea boots! With little to no heel, they offer all-day comfort and are versatile enough to suit a variety of styles. Many Chelsea boots are waterproof, making them perfect for rainy seasons as well.

Below, I’ve styled the chocolate brown Chelsea boots from Lands’ End in four different fall and winter looks. For an edgier option, my go-to has been the Sam Edelman lug sole Chelsea boots, which are durable, stylish, and my most-used pair.

A few things I’d like to mention about the chelsea boots from both brands:

The Lands’ End chelsea boots are a little shorter in the shaft and have a wider opening, so these are a better option if you have a thicker ankle. They’re very comfortable as well.
The Sam Edelman chelsea boots have a taller shaft and have a narrow opening, so these are more suitable for anyone with thinner ankles. Other than that, I love how comfortable and chic they are.

4 Ways to Style Chelsea Boots for F/W

Running Errands

If you’re needing to run some errands, but want to look chic and comfy — you can pair your chelsea boots with your favorite matching set, a chocolate brown coat [to go with the chocolate brown boots], and a sporty belt bag.

For the Weekend

ways to style chelsea boots for fall and winter cream sweater and jeans

EVERLANE SWEATER | LEVI’S 501 JEANS [SIMILAR JEANS] | SIMILAR SUEDE BAG | LANDS END CHELSEA BOOTS

For those Colder Days

For a cozy and athleisure-inspired look, I love pairing my Chelsea boots with the Aritzia Super Puff, an oversized sweater, and leggings. It’s the perfect balance of warmth and style, ideal for running errands or taking your dog for a walk on those chilly fall or winter days.

ways to style chelsea boots for fall and winter long puffer coat leggings

ARITZIA SUPER PUFF LONG | FRANK & EILEEN SWEATER | SIMILAR LEGGINGS | VARLEY BELT BAG | LANDS END CHELSEA BOOTS

For the Office

Chocolate brown is trending, so this outfit below is a perfect way to put together a chocolate brown look! This is also a great smart casual outfit for the office.