Chillier Days and Chunkier Sweaters : Summer To Fall Transitions

Fall... the season when all our inner divas are eager to dance around without the fear of salt stained booties. For summer loving Torontonians like me, this can sometimes be a bittersweet time. Fall means putting away our impulsive summer purchases, and saying hello to chillier days and chunkier sweaters. What I’ve learned over the years is that you don’t have to say goodbye to your summer wardrobe for your fall one. It’s both fun and easy to combine the two, and less heartbreaking for those like me who spend a ridiculous amount of money on summer pieces that we only get to use during the warmer days of the year. In this post, I’ll be sharing some of my go-to Fall looks, and how I layer up my summer wardrobe when the weather starts to dip. I was hoping to get this post published a few weeks ago, but school deadlines started creeping up and before I knew it I was catching up on a whole semester worth of stuff.

Thanks to this post I've realized I have SO MUCH to learn in the flat lay department and staging clothes is NOT an easy task! I have a newfound appreciation for those who do it, and would appreciate any advice from those who have figured out the whole lighting side of flat lay photography.

The way I layer and how much I layer definitely depends on how cold it gets. Some days are obviously warmer so I can totally get away with less. If you have a South Asian momma like mine, be aware that your mom will be convinced that you'll catch pneumonia of some sort if you walk out of the house with a dress or skirt anytime after September 1st. Yep.

Those of you who follow me on Instagram will know just how much I love t-shirt dresses and how often I wear them during the summer. Transitioning a t-shirt dress (or any dress for that matter) into a fall look can be easy, fun, and cost efficient. This t-shirt dress + jean jacket combo was my summer uniform this year. No, I really did over wear it. Whenever I transition a summer look into the fall, I work with what I'd normally wear and find ways to layer up to bring a cozier feel to the outfit.

JustFab jean jacket | Bluenotes t-Shirt dress | Chuck Taylors

In this case, I would substitute the jean jacket with a chunky cardigan or knit crewneck. I would wear black leather booties or long fall boots instead of the converses - I might even add stockings. The point is, I take what I already have and throw in some fall friendly pieces to bring together the look I'm going for. Trust me, it really does take some trial and error. I've found that having some basics in your closet helps with the whole transitioning process. Hudson's Bay is having their Bay Day sale, so all of their fall boots are currently on sale!

For anyone looking for stockings (...or are they called pantyhoses? I never know what to call them) take a look at H&M. I know I've mentioned this in a previous post, but they really do have some good quality options. If you want an even cheaper alternative, check Dollarama!

Knit J.Crew sweater | Oxfords from Journey's | Ardene crossbody bag

Comfort really is what drives my style, and wearing a dress or skirt is like hitting the jackpot in the comfort department. I found this J-Crew Factory sweater for 60% off at the Toronto Premium Outlet and instantly knew it would make the perfect addition for this look. The best thing about throwing sweaters over skirts is that it can also be done with a maxi. The even better part of wearing a maxi in the Fall, is being able to wear tights underneath without anyone ever finding out! 

Forever21 knit sweater | Forever 21 skirt | Fjällraven Kånken backpack | JustFab oxfords | Marc Jacobs watch | Polaroid PIC- 300 Instant Film Camera

My current Fall favourite has to be this this classic Kånken backpack that has made the perfect laptop bag and travel carry on ever!

Blue Jay's Hat | Sperry's | Levi's Jeans | Zara Basic Tee | Zara Raincoat

It has been raining quite a lot this month, and this bright yellow jacket is one of those purchases I'm so happy I made! I bought it at a Zara in Bogotá Colombia and I'm so grateful for my friends who convinced me to get it! I was very reluctant about buying a bright yellow jacket. But damn, I'm so happy I did because I wear it every chance I get. Sperrys and socks are also my go-to for as long as I can wear them until it starts snowing. These sahara coloured Sperry's, which can be found here, are also on sale right now!

Old Navy has a similar yellow rain coat in the men's section of their store. I got J a size small, but truthfully I could totally get away with wearing it too. I hope I haven't overwhelmed you with all these links. I just love a good sale and I know most of you probably do too. How do you transition your summer clothes into the fall? Are there any basics that make transitioning your clothes easier? Let me know in the comments below.

Speak soon!


A 24 year old Canadian living (& teaching) in Shenzhen, China.