Exactly How To Wear Your Winter Boots With Dresses This Season

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While jeans are definitely our trusted go-to wardrobe item as the weather cools, it can get a little boring to wear ankle boots with jeans and a jumper, day in, day out. But when denim has been your ride-or-die for decades, it can be pretty hard to feel confident in anything else — especially dresses in winter.

It’s not that all of us jeans-lovers have no idea how to wear dresses, we just get a bit overwhelmed by the idea of dresses in winter. When throwing on a pair of sandals and walking out the door isn’t going to fly in the chilly winter air, what does? Boots, that’s what. 

Here is exactly how to style dresses with boots in winter, so you can mix up that wardrobe and feel confident, even when you leave the jeans at home.

What Boot Styles Work With Dresses?

Look, we still love our ankle boots, but they’re not ideal for styling with dresses. Yep, even if that dress is long. Basically, you don’t want any skin to show if you’re wearing a dress that’s midi-length or longer (we’ll get to mini dresses later), so ankle boots are a risk. 

Jordan Boots

Sol Sana Jordan Boots. Image: Sol Sana.

Sol Sana makes some great knee high boots each winter, and this year, our pick is the tan Jordan boots ($349). That 10cm heel is perfect for giving summer dresses a bohemian feel.

Ives Boots

Billini Ives Boots. Image: Billini.

White boots used to be a niche market, but now they’re everywhere and with good reason; they work hard in a minimalist wardrobe and give basics a fun twist. The Ives by Billini ($139.95) is more of a cream-ivory shade, for anyone who’s scared of blinding white.

Haylex Boots

Wittner Haylex Boots. Image: Wittner.

Classic black, a sharp pointed toe and a structural heel — the Haylex boots by Wittner ($440) are a great wardrobe staple for anyone working in the corporate world, or for the all-black, everyday enthusiast.

How Can I Wear Summer Dresses In Winter?

You can absolutely re-purpose those floaty midi dresses you wore all summer in winter, but just make sure the pattern and style feels trans-seasonal. There is no blanket rule here, but you’ll know your dress is summer-only if it doesn’t look right with a coat or jumper over the top. Usually, it’s the pastel florals and brights that don’t make the cut, but that’s not definitive. A punchy, patterned summer dress can definitely work with some white cowboy boots and a fun knit, for example. 

Tie Dye Slip Dress

Bardot Tie Dye Slip Dress. Image: Bardot.

This effortless slip from Bardot ($139.99), plus some white cowboy boots, and an oversized knit makes the perfect weekend ‘fit.

Ginny Knit Jumper

Bec + Bridge Ginny Jumper. Image: Bec + Bridge.

Speaking of great oversized knits, this pick from Bec + Bridge ($240), with its great earthy hue, is going to work hard in your wardrobe as a layering piece for summer dresses.

What Boots Work With Mini Dresses?

I don’t know the science behind this, but for some reason, legs just don’t feel the cold the same way the rest of the body does. If you’re like me, then stop being scared of wearing a mini in winter. A velvet tunic or fun party dress looks amazing with knee or thigh-high boots, plus it means you’re going to feel totally temperate when you hit that cosy bar or dance floor. Rug up on top when you brave the elements, though — you’ll want a big coat, not a flimsy leather jacket.

Orbit Boots

Billini Orbit Boots. Image: Billini.

Chunky boots are still very much on trend, and these knee-high boots from Billini ($139.95) are the LBD’s best friend.

Moon Under Water Mini Dress

Alice McCall Moon Under Water Dress. Image: Alice McCall.

Not convinced about wearing your summer minis out in Arctic temps? Try a knit mini like this Alice McCall dress ($399).

What Winter Dress Style Is Best With Boots?

Boots are a great winter choice for rebooting (pun intended) your summer wardrobe, but for easy styling when you’re rushing out the door, pick up a few knit dresses. These are practically made to be worn with boots, and you can throw one on with minimal accessorising at the last second. 

Houndstooth Knit Dress

Veronika Maine Houndstooth Knit Dress. Image: Myer.

Everything about this knit dress by Veronika Maine ($289) screams corporate professionalism. If you’ve got an important meeting, this is going to be your wardrobe god-send.

Wide Rib V-Neck Dress

Glassons Rib V-Neck Dress. Image: Glassons.

On a more fun note, a fitted knit dress will work for weekends, workdays and everything in between. We love this v-neck piece by Glassons ($60) and can totally see it with some chunky boots at your next brunch date.

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