How to Wear Your Summer Dresses Now If It's Still Chilly Where You Live

I’m getting a little impatient to wear my favourite spring and summer pieces, and the Toronto weather isn't really cooperating, so I’m getting creative with layering.
Publish date:
May 19, 2014
dresses, layering, Spring Fashion, cardigans, summer dresses, How-To

For a long time I hardly ever wore dresses, feeling like something so feminine clashed with my queer identity. I always felt like I got a lot more unwanted male attention when I wore a dress or high heels, so I pushed them to the back of my closet to gather dust. Over the past few years though, I've found I'm happiest when I embrace my girly, cutesy femme style, regardless of the way I'm read when I do so. These days, I find myself reaching for dresses more than any other item in my wardrobe.

I love dresses so much that I have contemplated moving to California just so I can wear them year round. I love the freeing feeling of having bare legs, the swooshy feeling of the fabric as I walk around, the darling sweetheart cut necklines -- I love it all! Nothing quite makes me feel like a cutesy little fairy more than a pretty dress, and I actually find them more comfortable than pants and shorts most of the time.

The only problem is, wearing dresses when it’s not warm outside can be a bit of a challenge. I am definitely on Team Bare Legs when I can be, but even I’ll admit tights and high socks are necessary in the dead of winter and early spring... or in this year's case here in Toronto, very late spring. The weather here (and many other places) is still too cold to wear just a dress like all those lucky California people seem to be doing.

As a result of my undying love for dresses, coupled with me living in a place with very cold winters that last way too long, I’ve become a bit of a dress layering master, and have found a way to make almost every dress in my closet wearable year-round, day and night. It’s all a matter of finding the right layers:


Cardigans are the most obvious choice when trying to warm up your favourite summer dress. Long or short, thin or chunky, neutral or bold, cardigans go with pretty much everything your heart desires. I like pairing my cropped vintage cardi with feminine dresses, and my chunky long black cardigan with silky, dressy ensembles for contrast.


Another easy go-to, blazers are the answer if you don’t want to look too dressed down. I invested in a long, crepe blazer a few years ago and I love it so much for dressy occasions. a boyfriend blazer or fitted blazer can also do the trick, but comes off a bit more business, so might not be the ideal going-out option.

Collared shirts

Putting a shirt under or over a dress is one of my favourite layering tricks. In the summer, tying a sheer shirt over your dress can give you extra coverage, and in the winter, layering a thicker shirt with the right dress can help keep you warm and cute.

Warm hats

A knitted hat or faux fur cap, when matched with the right kind of dress, can help you keep heat in if the weather isn't quite up to snuff. I love wearing this light denim loose Fidelity dress with a casual sweater, loafers, and a warm chunky toque. Right now my favourite is this cozy grey number by Muttonhead, a Toronto brand that makes the comfiest clothing ever!

Tights and socks

I've discussed my love of high socks and tights before, but I felt the need to reiterate it here because these accessories really are so important when it comes to premature dress wearing. Invest in some fancy black knit tights for dressy occasions, and save cute patterns and thicker socks for more casual outfits.

Now go shop and get those dresses out of your closet!

Did I miss anything? How do you wear dresses when it's still chilly out?