Home Jeans Baggy Jeans 5 Winter Outfit Ideas With Sorel’s Brex Chelsea Boots

So when I got the Sorel Brex Waterproof Chelsea Boots in, with their non-slip, grippy bottoms & squishy walkable sole, I knew these would be in heavy rotation...as long as I could figure out some go-to outfit formulas.

5 Winter Outfit Ideas With Sorel’s Brex Chelsea Boots

December 26, 2021

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I almost always dress from the shoes up. Shoes (or boots) are the most weather- and activity-dependent, and I’m not one to suffer for fashion. So for each pair of shoes (or boots) that I own, I like to have a handful of go-to outfits I can rely on. That’s not to say that I don’t branch out, but it certainly makes getting dressed that much easier.

So when I got the Sorel Brex Chelsea Boots in, with their non-slip, grippy bottoms, and squishy walkable sole, I knew these would be in heavy rotation…as long as I could figure out some go-to outfit formulas. (Oh, and did I mention they’re waterproof, too?)

So I played around with some outfit ideas, trying to figure out which styles of jeans were well-suited to these boots, as well focusing in on my beloved joggers and leggings — could they, too, be worn with these chelsea boots?

Where To Buy Sorel Brex Waterproof Chelsea Boots

Before we get into it, these boots are selling fast. Below are a few places that still have an assortment of sizes in stock. In addition to the black with red bottoms, there’s also a white version available, a plain black version, and…and a really pretty olive green.

How To Style Sorel Waterproof Chelsea Boots With Jeans, Leggings & Joggers

I tested out the Sorel Brex Chelsea Boots with all of the different styles of jeans (wide-leg, straight-leg, skinny, cropped, flare, etc.,) and narrowed it down to my favorites. I also messed around with joggers and leggings, knowing that I’d get a ton more use out of these boots if they worked with some comfy pieces.

But the biggest hurdle? Coats. Trying to get the proportions of jean/boots/coats exactly right took some trial and error.

Lastly, a shout-out to this Clare V bag. It literally is the best bag to pair with Sorel’s red-bottomed chelsea boots. Foolproof.

1. Baggy, Wide-Leg Jeans + A Short Puffer Jacket

exact puffer, similar puffer | jeans (26) | bag | boots

My favorite jeans of late are these J.Crew high-rise boyfriend jeans. Because they’re so slouchy, a jacket that hits just past the hips isn’t nearly as flattering as a fitted, shorter one.

I love how these boots look peeking out from baggier denim. I finished the look off with a sporty, fitted sweater. The resulting outfit is easy, practical and cute.

sweater (s) | jeans (26) | bag | boots

Shop Short Puffer Coats

If you’re looking for loose fit jeans, I rounded up my favorites at the end of this article (including some with 34″ inseams for tall mamas).

2. Monochromatic With Joggers + A Fancy Coat

exact jacket, also in black & camel | sweater (s) | joggers (s) | boots

The exact pieces here aren’t important. The key to this outfit is that it starts with a base of casual, monochromatic pieces…and then a fancy(ish) coat is added. It’s like those ‘airport style’ photos all over Pinterest (think: matching sweatsuit with a long wool coat.) Same idea.

I also love how baggy joggers look with chelsea boots. It’s a newer silhouette that looks surprisingly polished, but in a totally effortless, nonchalant way.

exact jacket, also in black & camel | sweater (s) | joggers (s) | boots

Shop “Fancy” Coats

There’s a ton of different directions to take with this one…here are a few that caught my eye, all that I’d be willing to wear.

3. Cropped, Straight-Leg Jeans + A Long Parka

I love how jeans look just cuffed over the top of these boots; it really lets the pop of red shine. To get the proportions right, however, I found that a longer, 3/4 length coat works best. It hits exactly the right note of polished without overwhelming.

The longer coat also works with a longer top, too. In this case, I tucked Quince’s cashmere bat-wing sweater (a dead-ringer for the more expensive AllSaints one) into my jeans, but I could just as easily have left it untucked — the proportions would still work.

Shop Long Puffer Coats

This is probably one of my most-worn coats. It’s just the exact right shape and color to go with everything in my winter wardrobe, and is uber-practical, too. So it makes sense that THIS particular type of coat was really hard to find…almost everything is sold out. I rounded up my favorites, below. Many only have a few sizes left.

4. Leggings + A Short Puffer Coat

This combo works so well because everything is sporty: the boots, the coat, the leggings. And a peek of cozy sock helps the transition of the legging into the chelsea boot. (The leggings are those fleece-lined ones, too, for extra warmth.)

Shop Socks To Wear With Leggings & Chelsea Boots

5. Skinny Jeans + Hoodie + A Tailored Wool Coat

coat (6) | sweatshirt – more colors here | jeans (27) | bag | boots

While I think these boots do pair well with skinny jeans, the vibe is decidedly sporty. So a very tailored coat, on its own, looked a little silly with the boots, especially because the skinny jeans showed off the boots’ sportiness in all their red-bottomed glory. The leggings outfit (above) did as well, but that outfit was made of sporty pieces already, even without the boots.

A simple fix? I just need one more sporty piece to balance the look: a hoodie.