How to Style Your Summer Dresses For Fall

Fall is fast approaching and it’s soon going to be too cold here in Toronto to wear anything but jeans, a cozy sweater (layered over a thermal)(preferably that also covers your butt, a parka (or two) and boots that cover all the way up to your thighs leaving only a small small gap between the hem of your sweater and the top of your boots… it gets that cold…

While it’s always sad the cooler weather does provide more opportunity to layer, play with texture and not sweat. Fall is also one of my favourite seasons for fashion, not only is September fashion month meaning tons of street style inspo and new trends, but it is an opportunity to play with both your warm weather clothing and your cold weather clothing. One of my favourite ways to blend these two together is by styling my summer dresses with various fall pieces! I’m going to take you guys through how I would style my dresses through the different temperatures of fall!


Late August/Early September:

The weather here (in Toronto) is usually still really really warm. The nights are cooler and there is the odd chilly day, for the most part though it could still be the middle of the summer.

In styling a dress, since the weather is still almost summer I would pair the dress with a pair of combat boost or sock boots. Really, I wear dresses and combat boot combos throughout the summer when the temperatures are in the 25-30 degree range.

For the evening I would bring along a light sweater, oversized denim jacket or a leather jacket.


The days are getting cooler (for real now) but the sun still has a lot of warmth to it. Out in the day walking around, you would likely not need a jacket in the day. A light sweater layered, or a looser weft knit would be enough.

During the day, I would wear my summer dress styled in one of three ways:

Way 1:

A lightweight turtleneck sweater paired underneath a dress. In this circumstance, I’d usually wear a pair of sock boots to balance out the looseness of the dress and mirror the fitted turtleneck. Depending on my mood/occasion, I also sometimes belt the dress with a medium width belt to create some shape in the dress.

Belts I Would Pair With This Look:

Way 2:

A loose crewneck worn over a dress. The dress would act like a skirt more than a dress. I would pair a tight dress with an oversized sweater with a slightly cropped front and a longer back. With a dress with an A-line skirt or ruffly bottom, I would pair a cropped sweater (the more cropped the better). With either of these looks, I would simply pop on a pair of my trusted converse to keep everything casual.

Way 3:

A duster or cardigan thrown over a dress. Dress this look up by belting the cardigan, pairing with a pair of statement boots and throwing on a wide brim hat or keep it chic and casual with a pair of ankle boots and a page boy cap.

Early September – Beginning of October:

The cool weather has set in (it’s usually not cold yet, but no more days in the high 20s usually). My ride or die dress styling here is a turtleneck lightweight sweater OR a poplin shirt with some sort of flared sleeve action, worn under an A-line dress mimicking a pinafore. I’d usually pop on a pair of tights, a pair of super chunky lace-up booties and a plaid jacket.

Mid October or Whenever the Cold starts to get REALLY cold:

I honestly would probably gravitate to layering a turtleneck under a dress (like I’ve mentioned how many times?) BUT I would also wear my summer dress paired with a super snuggly oversized cardigan, belt it all together throw on a pair of ankle boots and hope and pray I don’t have to go outside too too much in that outfit. While in practicality if I was to go downtown or walk out for coffee I would put on tights but I personally think that this outfit is already REALLY tumblr for my own personal style and the tights would just increase the tumblr vibes.

OBVIOUSLY, my favourite way to wear my summer dresses is to throw on a turtleneck or a blouse underneath them. That’s just personally what I like, I think because I typically wear either very structured dresses or very ruffly, eyelet boho dresses that the turtlenecks and blouses either compliment the structure or “flowiness” of the dress or contrast with it. I’m all about the combination of structure with boho pieces or very feminine shapes with edgy accessories and this is what works for me ?

I hope you guys enjoyed this post!

xoxo Steph

PS! I’ve started a YouTube Channel! I’m posting videos every Sunday, Wednesday and Friday for the months of August and September!

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