Style Notes with Sim: What Shoes to Wear With Barrel Jeans
Featuring Sim from @sim.spys.stylist
You’ve probably spotted them popping up everywhere — that cool, slightly quirky shape of the season: barrel leg jeans.
This week, I asked Personal Stylist — Sim, aka @sim.spys.stylist — to break it down in her signature no-fuss, real-mum-friendly way. If you’ve got a pair of barrel legs sitting in the wardrobe, this one’s for you.
How to style barrel leg jeans with the right shoes (without overthinking it)
By Sim from @sim.spys.stylist
If you’ve been here a while, you’ll know I love a good barrel leg jean. They’re comfy, a bit edgy, and they instantly make an outfit feel fresh. But one of the most common questions I get is: What shoes do I wear with them?
Let’s break it down in the simplest way possible, so you can actually wear them (instead of letting them collect dust in the wardrobe).
1. Cropped barrel leg & open shoe (but not open toe)
This is one of my favourite combos. In my recent reel, I styled a cropped barrel leg with a shoe that’s open on top of the foot — not an open-toe sandal, but something that shows a bit of skin across the foot.
Why? Showing that bit of the foot helps balance the volume of the jeans and gives the outfit a lighter, more effortless feel.
I also chose a pointy-toe option here to elongate the leg. A pointy or almond-shaped toe draws the eye down and gives the illusion of extra length — especially handy with a barrel leg shape that can sometimes cut you off visually.
Suggested styles below:
Tony Bianco | Cherry | $199.95 > (The exact style that Sim is wearing in the reel)
2. Cropped barrel leg + boot
When you’re wearing a boot, think about the shaft (the part of the boot that hugs your ankle and lower leg).
The trick here is to make sure the shaft of the boot tucks nicely underneath the denim. We don’t want that awkward bunching or gaping.
A slim-fitting shaft helps keep the silhouette clean, so the jeans still feel relaxed and modern without swallowing your legs.
Suggested styles below:
Witchery | Kate Boot | $249 > (The exact style that Sim is wearing in the reel)
3. Longer barrel leg + pretty much any shoe (but let’s be smart)
If your barrel leg jean is longer, the good news is — you’ve got more flexibility.
The length covers more of the leg, so there’s less focus on where the hem ends and more on the overall vibe. But that doesn’t mean you can throw on any old shoe and call it a day.
Even with a longer length, if you want that elongated leg line, stick to a pointy or almond toe where you can. It’s such a small tweak, but it really does make a difference.
Suggested styles below:
A quick summary from Sim…
Barrel legs can feel tricky, but they’re actually super versatile once you get the footwear right. It’s all about balance, showing a little skin where it counts, and paying attention to those small details that help you feel more put-together.
Have a pair sitting in your wardrobe waiting for a moment? This is your sign to get them out and have a play!
Want more easy outfit formulas and clever styling advice?
Follow Sim on Instagram @sim.spys.stylist — she's a go-to for chic looks that actually work for real life (think kinder drop, errands, and the occasional date night).
And if you loved this post, hit the ❤️ or forward to a friend who’s also baffled by barrel jeans.
Mum Mode x