How To Wear Chelsea Boots With a Sweater Dress

Chelsea Boots might be one of those things that you don’t know that you actually like…or maybe you don’t know that what you’re looking at is considered a Chelsea Boot!

By definition, these boots are “close-fitting, ankle-high boots with an elastic side panel that often have a loop or tab of fabric on the back of the boot, enabling the boot to be pulled on.” They were made popular in 1960s Britain, which is likely why we see them come up in Fall Fashion every year.

Until recently, I’d considered Chelsea Boots to be a bit more masculine than my personal style would allow…until I actually tried them on! I tried a few different pairs but settled on these gorgeous UGG Bonham Boots for a ton of different reasons…

About My UGG Chelsea Boots

Shown: UGG Women’s Bonham II Boot (Black)

First of all, these aren’t your traditional UGG boots! Although they are cute with leggings and insanely comfy, these boots are more grown up. These boots are tailored, they have a slight heel (makes your legs appear more toned!) and they’re made of waterproof leather.

They still have the same quality and warmth that you’d expect from UGG footwear but with a modern feel. I love the texture of the black “sueded” leather because I feel like it adds some dimension to my outfits.

Also, let’s be honest. I live in a cold climate and I spend a lot of time in hockey rinks. These boots are super warm and really grippy, so they’re great for my day-to-day activities and because they’re waterproof, sometimes I can wear them in lieu of snow boots.

P.S. These come in a super cute grey/brown shade, too: Bonham II Boot (Dove)

How to Style Chelsea Boots

My Fave: With Cuffed Jeans + Sweater

Shown: UGG Women’s Bonham II Boot (Black) | Lolë Mika Dress (Gelato Heather)

This is my favourite way to wear these boots because well, I live in jeans, sweaters and boots from October to March! I love cuffed jeans and this Lolë sweater dress was just short enough to wear as a top!

Sweater Dress + Tights/Leggings

Shown: UGG Women’s Bonham II Boot (Black) | Lolë Mika Dress (Gelato Heather)

I chose to wear this dress with tights, but it is equally cute (+ slightly warmer) with leggings and these boots. You could also try adding wool socks over the leggings/tights for a more Canadiana look!

Looking for a similar dress but in a darker shade? This Lolë Mika Dress comes in 3 other “heathered” colours: Grey (Light Grey Heather), Burgandy (Windsor Wine Heather) and Black Heather!

Sweater Dress Alone!

Shown: UGG Women’s Bonham II Boot (Black) | Lolë Mika Dress (Gelato Heather)

Think of this as a Fall-Transition look! I did shoot this on a cold day (can you tell?!) but on a pleasant fall day, this look is great. Add a cute cross-body bag or a big scarf and you’re gtg. I love how this dress features different knit patterns/textures and a slight cowl neck making it oh so cozy!

Other Dress Ideas: Why not try a cute knit midi dress or a midi skirt with a cable-knit turtleneck?

New Fave Shop: Altitude Sports

I purchased these boots and this dress from Altitude-Sports. It was my first time ordering from them and it was excellent. I’ll definitely be ordering from them in the future – they have a ton of options, super fast shipping and they’re based in Canada! My S.I.L. brought them to my attention when shopping for outerwear for my little niece and I was hooked immediately! You might hear the word “sports” and think it’s all parkas and backpacks (don’t worry, they carry those, too!), but the they are So.Much.More. Take a gander through their brands list and you’ll know what I’m talking about!


Love This Post?

Subscribe to get posts like this delivered to your inbox every week

Carlee Krtolica
Carlee Krtolica