Style Deep Dive: How To Wear Horseshoe Jeans (Spoiler: There’s No Wrong Answer)


This probably comes as no surprise, but I own a lot of jeans. And while I definitely have a few tried and true favorites that I turn to again and again (and again…hiiii, 501’s!), I’m pretty agnostic when it comes to worshipping any one style of denim. Which means this anything goes moment that’s happening with jeans right now is strangely, quietly thrilling.

It’s afforded me the opportunity to look at the meticulously stacked rows of denim lining my closet with fresh eyes. And it’s inspired me to collect a few new pairs of denim in silhouettes that are shockingly fun and easy to wear. Wide legs, cargos and barrel jeans — oh my.

What Happens When My Favorite Jeans Ever Go On Steroids? All Good Things.

The latter of that trio — barrel jeans — are some of my favorite jeans I’ve ever worn. They feel effortlessly cool, are equal parts fresh and nostalgic (there’s a vintage vibe to them, for sure), and wear almost more like trousers than jeans.

So when the next wave of barrel jeans, made their way into my feed — this time called “horseshoe jeans” and featuring an even more exaggerated bowed leg shape made possible with dramatic darts and seaming — I was almost immediately sold.

I mean, of course I was. They’re like barrel jeans…on steroids.

top (S) | jeans (TTS, 25)

A few weeks ago, I finally snuck into an Anthro fitting room to try on the pair that has been stalking me most successfully around the internet: the Pilcro Heritage Curve Mid-Rise Wide Leg Jean (say that 10 times fast). While these don’t technically have “horseshoe” in the name — ahem, here’s where I admit that very few jeans of this style actually have horseshoe in the name, but Citizen uses that name for their very similar silhouette, and it seems the most aptly descriptive — they’re absolutely the pants that come to mind when you hear phrases like there’s gold in them thar hills. And if Yosemite Sam were content to wear his boots under his jeans rather than tucked inside, I’m fairly certain these would be his No. 1 choice.

top (S) | jeans (TTS, 25)

Shop More Barrel and Horseshoe Jeans

In short, these Pilcro Horshoe Jeans (yes, I’m just going to call them that) and others like them are super freaking fun, with a whimsical quality unlike anything else I own. And the best surprise of all — they’re almost foolproof to style.

To be clear, that realization didn’t strike until after the jeans came home with me. I fell in love with them in the fitting room wearing little more than a cropped white tee and flip flops, but as soon as we shared that image on social, people began asking: how else would you wear these?? And, more timely, which shoes would you wear these with for fall?

So I pulled out some of my favorite fall pieces — really, just some of my most-worn items that were either fresh out of the wash (or living at the foot of my bed, if you need a true testament to how often I reach for them) — and did a bit of a deep dive into the best footwear, tops and fall layers to pair with all jeans barrel and/or horseshoe.

How To Style Barrel or Horseshoe Jeans For Fall (It’s Simpler Than You Think)

I’ll drop a few a-has! below, but what I really learned is that, for my personal style, at least, horseshoe jeans add a quirky, cool element to just about anything, despite their seemingly tricky proportions.

Here are some quick takeaways for what pairs exceedingly well with barrel jeans, big and small:

  1. Cropped(ish) tops. Fitted or boxy, a cropped top highlights the nipped in waist on horseshoe jeans and allows you to appreciate the full, balloon silhouette of the leg and any fun tailoring details at the waist (like the darts on mine). I loved the look of these jeans with a cropped white t-shirt, but for more practical fall layering, a short, boxy cotton or cashmere sweater would be easy. If cropped isn’t your thing, try a tuck with a belt.
  2. Higher shaft boots. If the jeans you’re eyeing are a little cropped, like mine, a higher shaft boot keeps the draft out while also making for some nice continuity in the ankle zone. I like the look of something with a heel for a little drama, but that’s personal preference. These jeans are even voluminous enough that you could put a full pair of knee-high boots underneath and no one would be the wiser. 
  3. Just about any sneaker. A chubby dad sneak for a bit of trendier look, checkered Vans or skate shoes for a casual, California vibe or high-top Converse for an off-duty model thing. Easy.
  4. A voluminous top layer. I played around with an oversized camel blanket coat, but I think anything up top that’s a bit shapeless pairs well with the bowed shape of the pants. A chunkier oversized cardigan or a masculine plaid blazer could be cool for a casual office look. If you plan to wear the top layer open, keeping anything underneath cropped or tucked and belted (see: #1) helps balance things out.

7 Easy Outfit Ideas Featuring Horseshoe Jeans

If you’re still reading at this point, congrats! Your reward is now the eye candy that is me standing in more or less the same pose in seven outfits that prove just how versatile barrel jeans can be. Hurrah! Here we go.

1. Horseshoe Jeans With A Boxy Sherpa Jacket + High Shaft White Boots

top (S) | jeans (TTS, 25) | boots (TTS, or here)

top (S) | jeans (TTS, 25) | boots (TTS, or here) | jacket (XS, try your luck here)

Shades of white and denim, yes please. I shouldn’t love the way the ivory boots accentuate the cropped length of the jeans rather than elongating the whole look, but I do. Subtle western vibes in the boots and jacket mirror the barrel silhouette, so there’s a natural ease about this look that, unsurprisingly, gets a big ol’ thumbs up from me.

2. Horseshoe Jeans With A Black Turtleneck + Statement Boots

top (XS) | jeans (TTS, 25) | boots (or here) | similar sweater | similar belt | bag

These boots. I know this post is not about them, and, frustratingly, they’re a bit hard to find in stock at the moment (wait!! I just found them here and here!), but these boots. They’re a gorgeous tapestry fabric with a leopard print heel, and they just beckoned. But that’s beside the point. Grab any pair of high-shaft booties in a punchy color or a luxe fabric, pair it with an all-time classic black top and call it a day. For an added layer of warmth (and interest), I pulled over an almost open-knit shaker stitch sweater in 100% cotton. And I don’t hate it.

3. Horseshoe Jeans With A Black Turtleneck + Ballet Flats

top (XS) | jeans (TTS, 25) | ballet flats (TTS) | similar belt | bag

Little bit of Wrong Shoe Theory here, where we’re matching the tougher, more structured denim with a daintier flat and that same tissue turtleneck. All of a sudden we’re shopping. We’re brunching. We’re school conferencing. We’re trying just hard enough, which is hardly at all.

top | jeans (TTS, 25) | ballet flats (TTS) | similar coat | bag

Does she work with an oversized wrap coat? Well yes, she does. And I have to be frank here: I almost like this look best of all, if only because the wide denim is almost evocative of a skirt the way it’s peeking out from beneath the blanket coat. There’s something that’s equal parts sophisticated and carefree and maybe even a little French about this one, and that’s never a bad thing.

4. Horseshoe Jeans with A Cropped Black Tank + Western Boots

similar top | jeans (TTS, 25) | similar boots | similar belt | similar cardigan | similar bag

There’s something undeniably hopeful and romantic, even, about black western boots and a little cropped top. The ideal date night outfit.

similar top | jeans (TTS, 25) | similar boots | similar belt | similar cardigan | similar bag

And since it’s highly unlikely that I’d step out for date night in Half Moon Bay without a layer, this look works with a longer cardigan, too (in an ideal world, I’d pair it with something even more oversized). A little bag that matches the teenyness of the top feels fun here (and I’ll take any opportunity to rock a small bag when I’m sans baby). I’d love this outfit just as much with high tops, too.

5. Horseshoe Jeans With An Oversized Puffy Vest + Ballet Flats

sweatshirt (S, or here) | jeans (TTS, 25) | ballet flats (TTS) | vest (S)

Some iteration of this outfit has been my drop-off uniform for the past month or so. The oversized vest is absolutely clutch — the pockets keep my phone handy and my hands warm on the walk to school, and it feels on-trend despite the fact that it’s not at all trendy. And adding these flats to almost any outfit always makes me feel a wee bit more dressed. The fact that it all works just as well with these jeans makes my little “here for the smallest of thrills” heart absolutely sing.

6. Horseshoe Jeans With A Sweatshirt + Vans

sweatshirt (S) | jeans (TTS, 25) | vans

Unapologetically here to report that yet another iteration of a sweatshirt works here. Think of this outfit as the “before” in those “wearing vs. styling” posts. This is, of course, fine for the playground, but to up the effort, add a skinny black belt, a big functional tote, and sunnies and/or a ball cap. Done.

7. Horseshoe Jeans With A Sweatshirt + Dad Sneaks

sweatshirt (S) | jeans (TTS, 25) | sneakers (size down half) | similar coat

Of course, I couldn’t not swap in a pair of dad sneaks, and I’m pleasantly surprised to say that they’re just as good with these horseshoe jeans as they are with some of my favorite full-length baggy jeans. I kept white socks in the equation (file under: things I never thought I’d be caught dead saying) and topped it with that blanket coat again, but a big plaid shacket would be cool here — and while I’m genuinely sad to report that I rarely feel I can pull off a ball cap, one would be an excellent addition here, too.

Obviously there are countless other ways you could style these — with truly dressy heels (these perfectly minimal slingbacks!), or loafers, or those plush sherpa UGGs that we hate to love. Consider a utilitarian trench, or even a structured, corset-y number for an over-the-top date night. I genuinely think it would all fly with these, and can’t wait to see — and wear! — more of it all in the real world this season.


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