How to Wear Your Summer Dresses Through Winter

I have an inability to decipher between “winter clothes” and “summer clothes”. Blame it on two years of living in Sydney and never really having a winter, or blame it on the fact that I hate having to stop wearing bright colors and flowy skirts just because of sub-zero winds and a little bit of snow. Either way, I used to think just throwing a pair of tights on under a light summer dress in the middle of winter was enough. Then I’d get outside and be all WHY AM I SO COLD?

It wasn’t the fact that some thin little dress and a pair of black tights under my coat was never gonna to cut it. It’s just that it was too cold. duh.

So I keep wearing them. I love how unexpected it is to walk out of the house on the 1st of December in a bright orange dress. I love how it adds a pop of color to an otherwise dull seasonal color palette. Plus I love my dresses and I want to wear them all the damn time because jeans aren’t actually that warm in winter either.

Here’s how I’ll be clinging onto styling my light weight dresses through my least favorite season.

With Boots

How to wear summer dresses through winter

How to wear summer dresses through winter

How to wear summer dresses through winter

Dress – Terminal 21 Bangkok // Boots – Banana Republic (similar) // Boot Socks – Old Navy

Boots are an essential in winter – heeled or not, they’ll keep your legs warmer than any pair of jeans or thick tights ever could. Wear them with a pair of boot socks for a cute layered look (and added warmth obvi). I LOVE these grey boot socks because they go with all my boots and all my dresses. Best color decision made by me like 5 years ago ever.

With Layers Underneath

How to wear a cowl neck

How to wear a cowl neck

Details for this outfit are in THIS POST

This is an essential that I’ve only just started playing around with. I LOVE layering a long sleeve or roll neck underneath a lighter dress for so many reasons, the main one being it makes the dress SO much warmer. It’s also such a nice contrast of textures and weight. It’s made me really want to go out and buy a few more long sleeve knits.

With Cardigans

How to wear summer dresses through winter

How to wear summer dresses through winter

How to wear summer dresses through winter

Dress – Korea // Shoes – Clarks // Cardigan – J.Crew // Belt – Lord and Taylor

Add a cardi, belt it. Play around with different colors. Throw different patterns top. The whole point of wearing your summer pieces through the winter is to keep things fun and exciting. To make yourself feel like it’s not minus 5 outside and that that’s only a bit of snow and it totally isn’t going to turn into ice overnight.

With Sweaters

How to wear summer dresses through winter

How to wear summer dresses through winter

How to wear summer dresses through winter

Dress – Korea // Boots – Michael Kors (only available in DSW Stores) // Sweater – Talbots (currently 40% off!)

I never understood this one until I started trying it. The key, I think, is to get a sweater that falls right at the waist of the dress (or roll it underneath and belt it to make it sit in that spot). It keeps the shape of the dress and defines the skinniest part of your middle all at the same time.  I also like this combo because this dress has a collar which sticks out of the top, so you’re getting the color contrast from both ends of the sweater. I feel a bit like a sassy little school teacher in this (although, having been a teacher, I would never wear this to work because children have sticky hands and ick).

The most important thing is to have fun with it. If you feel comfortable and confident in what you’re wearing, you’ll look good.

Do you cling onto your summer clothes through all the seasons? Or do you prefer to ditch the brights and ease into winter in neutrals? 

Laura Bronner

6 Comments

  1. I started wearing sweaters with my dresses last winter and it was straight up life changing. Thanks for all the tips!

    • RIGHT? Where have I been? It’s hard to change your ideas about how something is going to look – I’m glad I’ve finally started doing it!

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