Barrel Overalls Are A Thing! Here’s How I’m Wearing Them For Winter.


I adore a barrel pant, and I’ve talked at length about their beefier cousin, the horseshoe jean. The exaggerated bow-leggedness makes everything they’re paired with more interesting, which manages to make getting dressed, in general, more interesting.

And that’s really the goal with personal style, isn’t it? To surprise and delight and attract interest via your clothing — even if only from yourself? Let’s go with yes.

Free People barrel overalls, camel coat, lady cardigan, western boots, quilted bag, pom beanie, winter outfit idea

overalls (s) | cardigan (xs) | similar coat | similar boots | similar hat | similar bag

I also, as the record has shown, love overalls. I wore the hell out of them when pregnant, but they’re also one of the first things I reach for when I genuinely don’t know what to wear. Overalls are almost never too try-hard. And as long as you have a little patience for getting in and out of them come when nature calls, they’re an intriguing match for just about everything.

They are, for lack of better word (and, again, potty function), easy.

Little Bit Obsessed With: These We The Free Good Luck Barrel Overalls

So it comes as absolutely no surprise that these We The Free Good Luck Barrel Overalls were more or less made for me. So clearly, in fact, that I didn’t even have to buy them for myself. Nope. They were a Christmas gift from my mom, who (thanks to an Instagram ad, no doubt — that woman is an admitted sucker for in-feed ads) saw them and instantly thought “oh, these would be right up Em’s alley.” And she (with a little help from the algorithm, as it may have been) was so very right.

So far, I’ve paired these guys with everything from a ribbed tank bodysuit and Birkenstocks to a cropped hoodie and ballet flats, but the combo I’ve been donning most on these cool winter days is exactly what you see here:

Together, the entire ensemble strikes that perfect balance of masculine and feminine. Functional and funky. Understated and intentional. And thanks to the volume of the pants? They’re almost a little…well, dressy isn’t the right word. Nor is fancy. But dressy-adjacent? Luxe? You know what I mean.

Free People barrel overalls, cropped sweater, western boots, winter outfit idea
Free People barrel overalls
Winter outfit idea, pom beanie, camel coat, cardigan
Free People barrel overalls, camel coat, lady cardigan, western boots, quilted bag, pom beanie, winter outfit idea

overalls (s) | cardigan (xs) | similar coat | similar boots | similar hat | similar bag

An Easy, Elevated Winter Outfit Featuring Barrel Overalls? Yes Please.

I always love the challenge of dressing for real winter. We don’t get a lot of it here, but we get plenty of year-round cold, so taking pieces that are fun and a little bit funky and adapting them for brisk wind and mucky dirt trails and, uhhhh, real life is still a thing.

This is an example of the kind of outfit that just tickles me when the temps drop. Warm, comfortable, playful and a little bit elevated. It’s all I can ask for. Here’s how it breaks down.

1. Start With These We The Free Good Luck Barrel Overalls

Playful and utilitarian and, like everything Free People, a little bit boho, these We The Free Good Luck Barrel Overalls have enough personality that you don’t have to think much about the rest of your outfit. The denim is heavier weight than many of the overalls I own, which makes them ideal for fall and winter, but I’ll absolutely still be wearing them with a tank top and vans or Birkenstocks come summer. (Even now, that’s how I’ve been wearing them around the house or for quick jaunts to the park when the winter sun decides to show its shockingly warm face.)

Unsurprisingly, they’ve got the same exaggerated profile of the We The Free Good Luck Barrel Jeans, with the structured seams adding even more volume. And they have a truly nipped-in waist, as far as overalls go. I actually have to release a side button or two to get them over my hips, but then once they’re on, they’re loose and roomy and comfy as can be.

Free People overalls, lady cardigan, western boots, winter outfit idea

overalls (s) | cardigan (xs) | similar boots | similar bag

As far as sizing goes, my mom ordered both an XS and a small for me to try. Typically, Free People everything errs a little on the larger side, but I was surprised to find that these rode up a bit in the XS and I had to let the straps out more than I’d like to have them hit just right. (For the record, I’m 5’5″, slightly long-waisted.) So I went with the small here, which is perhaps a little roomier everywhere else but fits perfectly in the length, with wiggle room to boot. If you’re typically between sizes and you’re either tall or long-waisted, I’d go with the larger of the two.

2. Add A Flirty, Feminine Cardigan

lady cardigan, quilted bag, winter outfit

overalls (s) | cardigan (xs) | similar bag

As someone who more or less collected vintage, embellished cardigans and little lady jackets in high school, the return of tiny feminine toppers makes me very excited. My style is admittedly very casual, but the addition of a piece like this pearl button cardigan goes a long way, injecting a little flirty effort without requiring any real effort at all. It’s a nice complement to the masculinity of the overalls.

Really, any softly structured piece with a little bit of “lady”-ness will do. I’ve rounded up a few more I really love, below.

3. Keep Things Grounded (And Functional) With Western Boots

Free People barrel overalls, how to style

overalls (s) | cardigan (xs) | similar boots

I think my biggest takeaway from that video I did about styling horseshoe jeans is that the accompanying footwear really isn’t as tricky as you’d think. So many styles of shoes work here, but for drop-off or wet weather errands, I’ve been reaching for a pair of not-overly-gimmicky western boots.

These are 10 years old, with a softer, more almond-shaped toe, and they’re comfy. They feel naturally made for the barrel silhouette and, when paired with softer pieces, aren’t as costumey as you might think. If I had to buy something similar today, these Tecovas boots have a super similar vibe and are, in fact, just plain gorgeous. (I’m obsessed with them in the Sequoia color, too.)

4. Bundle Up With A Belted Wrap Coat

Free People barrel overalls, camel coat, lady cardigan, western boots, quilted bag, pom beanie, winter outfit idea

overalls (s) | cardigan (xs) | similar coat | similar boots | similar hat | similar bag

Adding something soft and slouchy to an otherwise utilitarian situation just seems to work (while simultaneously looking even a little but chic). Bonus points if that something souchy is a rich neutral. Plus, hiiiii, it’s actually warm.

If you don’t have a wrap coat (either a lined one or an unlined blanket coat that’s even easier to layer up in moderate climates), this one is very similar to mine. And the butterscotch color of this one looks so rich (it’s also on sale!).

Hell yes, overalls.


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Photos by Carolyn Stockman. Thanks, friend!

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