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Seasonal Fashion: How to Transition Summer Pieces into the Fall Months


Transitioning Summer Clothing into Fall

Before you know it, summer’s long days will be fading away while cooler weather gradually creeps up on us. Cue the yearly wardrobe panic and sudden lust for cozy knit sweaters, hardy denim and fur-lined parkas. But hold on just a second: don’t relegate your summer lineup to storage just yet. Most of those seemingly flimsy pieces are actually highly versatile transitional wardrobe assets in disguise. Don’t believe us? Check out our tips for transitioning summer apparel to fall, and thank us later.

  1. Try an unexpected pairing

Transitioning from Summer to Fall in an Unexpected Pairing

Photo credit: Memorandum

Pairing summer staples with fall-weather-appropriate pieces not only allows you to increase your potential outfit options, it also creates unexpectedly fresh mid-season looks. Not sure what we mean? Here are some perfect pairing examples.

Summer Dresses

That perfect summer maxi dress you wore all summer long? Pair it with a chunky sweater, belted blazer or leather jacket and throw on a pair of heeled ankle boots for the perfect casual fall outfit.


Bright summer shorts, paired with the right dark or neutral fall colours, can provide a welcome and unexpected pop to fall fashion. Pair them with tights, close-toe pumps, a t-shirt, blazer and scarf for a chic yet playful look.


The last piece you’d expect to repurpose is actually your secret weapon for fall. Wow everyone with a fierce jumpsuit paired with a blazer, pumps and a stunning bag for your new autumn power outfit.

  1. Layer up

Photo credit: Bonae L’Amour

Those breezy tees and tanks that were your salvation during those sizzling summer months will be your best friends come fall thanks to the beauty and practicality of layering.


Summer t-shirts become the perfect base layer for cooler weather staples like sweaters, cardigans, blazers and leather jackets. For extra warmth, layer two different (but complementary) coloured t-shirts for something a little different.

Tank Tops

Tighter fitting summer tanks make the perfect undershirts for a little extra warmth under lighter tops, like silk blouses or light sweaters. For some unexpected panache and proportion play, try wearing your long, loose summer tanks under shorter turtlenecks and boxy sweaters, allowing the hem to hang out for a cool layered look.

  1. Go long sleeved

Photo credit: Greg Kessler

All most of those summer bottoms (think: skirts, light pants, shorts and dresses) need are long sleeves on top to make the leap into fall.


Long/short proportions in fashion are always pleasing to the eye and the summer-to-fall transition is the perfect time to have some fun with them. Pair shorter summer skirts and shorts with long sleeved blouses and turtlenecks for some easy, elegant autumn outfits.

Light pants

Loose harem, tight cropped denim and lightweight straight legged summer pants play nicely with long sleeved shirts, blazers and pumps. The options here are endless!

  1. Walk the walk

Photo Credit: Alyssa Lau

We hardly need to tell you that the right shoes can transform an outfit. Nowhere is this truer than for transitional wardrobes. A couple of strategically-chosen pairs of classic fall shoes will take your summer pieces from the beach to the classroom in no time.

Closed-toe pumps

You may have noticed a trend already, but most summer staples can be easily updated with the addition of a demure, fall-toned pump—think oxblood, navy, black or taupe.

Ankle boots

Turn in your sandals for a pair of versatile heeled ankle boots for an instant fall appropriate fashion update. They’re perfect for day or night, and an effortless autumn outfit is as easy as pairing them with shorts, skirts, pants or a maxi dress and a couple of well-chosen accessories.

  1. Add an accessory or two

Photo credit: Clarabelle

We love our accessories and make no mistake, these seemingly innocuous wardrobe add-ons will be your best friend when transitioning between the summer and fall seasons.


Scarves take centre stage in the fall, allowing you to layer summer staples while drawing the eye to your season-appropriate scarf. These cozy pieces are also perfect for adding some much-needed warmth on those not-quite-warm but not-quite-chilly days.


We’ve been thanking the fashion gods for the comeback hats have had recently, particularly wide-brimmed fedoras and floppy hats. Remember that maxi dress paired with a chunky sweater and ankle boots back in rule #1? Clinch the look with a chic felt hat for an effortless boho vibe.

Top photo credit: Tommy Ton

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