Seasonless dressing: 5 Style Panel tips for wearing your favourite summer pieces all winter long

We may be mid-blizzard season, but thoughts of tank tops and sunny weather have us wishing we were a million miles away. And while we can’t deny that winter’s demise is still at least a month away, one creative way to wish winter away is by wearing some of our most beloved summer pieces while it’s still cold outside.

But how to master seasonless dressing without dying a million blizzard deaths? Take a cue from our Style Panel, who has seamlessly integrated summer pieces into winter wardrobes.

Kira Paran takes a page out of Prada’s fur-for-spring book by pairing her cozy fur topper with a sporty baseball cap. Meanwhile, both Kayla Short of Short Presents and A Fashion Love Affair’s Cara McLeay layer summer dresses overtop long sleeve tops.

The end of winter can’t come soon enough, but trying some of these Style Panel-approved tips might speed up the process. Come spring time, you’ll already be ahead of the game.

Challenge 91: What are your tips for wearing summer pieces during the winter? Read the answers now! »


Alexandra Grant, 26
Vancouver | To Vogue or Bust

As the weather warms up here in Vancouver, I find the crossover with my spring and winter pieces is growing larger and larger each day. To keep the transition seamless, I only ever incorporate one piece at a time – for instance, these lightweight printed pants look completely at home in a winter-apropos look thanks to the layered leather and cashmere pair. Whether it’s a sundress or a light silk blouse, keep it to one item while it’s still cold out and work your outfit around it!

Alex’s wearing: Leather jacket, Walter Baker. Cashmere sweater, Joe Fresh. Pants, Scotch + Soda. Heels, J.Crew. Bag, Roots.

Photography by Trevor Negin

 Barbara Ann Solomon, 26
Toronto | Barbara Ann’s Style Blog

A winter wardrobe can be very limiting, as there are only so many shirt and sweater, skirt or pant, combinations you can do before even the biggest wardrobes get boring. To add interest into your look, add some pieces from your summer closet to create an unexpected layered look. The key thing to ensuring your summer pieces look appropriate in the colder weather is the layers. Layer to add texture and drama, the majority of your look should still be seasonally suitable.

Barbara is wearing: Sweater dress, American Apparel. Summer dress, Banana Republic. Shoes, Topshop. Jacket, Danier.

 Cara McLeay, 28
Vancouver | A Fashion Love Affair

I love easy summer dresses and often wear them during the cooler months layered with other pieces to stay warm! A strapless dress is usually off-limits in the winter, but by layering a denim shirt underneath, it instantly updates to a winter appropriate look!

Cara is wearing: Shirt, American Eagle. Dress, Zara. Bag, Prada. Shoes, Shoemint. Watch, Fossil.

Kira Paran, 29
Edmonton | Northern Style

I am a strong believer of utilizing SOME of your summer pieces in the winter months. My two rules: 1) If the summer item is a neutral colour and doesn’t involve a crazy summery print 2) The material is substantial enough to be wore in colder temperatures. It could be a thick knit maxi dress or in my case, a baseball cap can transition to the colder months if it can still function in winter temperatures.

Kira is wearing: Fur popover, Banana Republic. Shirt, Club Monaco. Pants, J.Crew. Baseball cap, J.Crew. Boots, Sperry.

Kayla Short, 26
Halifax | Short Presents

Ordinarily this stripped summer skater dress would never see the the light of day in winter, but layering it over a long sleeved shirt, tights and boots makes it more weather (and season) appropriate. Rather than pair the dress with an over-sized cardigan (and cover up the dress) I decided to layer under it, so the dress still gets its shinning moment. It didn’t wait all season just to play peek-a-boo.

Kayla is wearing: Necklace, Shop for Jayu. Dress, Old Navy. Waffle T-Shirt, Gap. Tights, Joe Fresh. Boots, Very Volatile. Cross-Body-Bag, Forever 21. Sunglasses, Polette Eyewear.

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