Transitioning my Wardrobe From Summer to Fall

It’s always bittersweet saying goodbye to summer. With days getting shorter and nights getting longer, the weather turning cooler, and patio season drawing to a close there are many things that make me instantly nostalgic for hot summer days. While summer is fleeting, fall fashion is the foundation for your winter and early spring wardrobes for the coming year.

My first step in transitioning my wardrobe from summer to fall is switching out my clothing pairings. At the end of August/early September here in Ontario we have some of the most unpredictable weather, it can be hot and humid one day to rainy, cold and miserable the next. The first step in my choosing an outfit for the day is the weather forecast, knowing how hot the day is going to be and how cold the night is going to get plays a huge role in what I’m going to wear. The weather considered I move on to the pieces that are practical for the temperature, on average early fall tends to have warmer days and much cooler nights, which usually causes an excessive amount of sweater/short combos.

I have five steadfast go-to’s while dressing for the fall…

Chunky Knits + Shorts + Tennis Shoes/Boots/Booties

Lightweight Knits/ Thermals + Skirts + Booties + (tights or knee socks optional)

Denim + Thermal + Tennis Shoes

Midi Dress + Bomber/Leather Jacket + Tennis Shoes

Duster Cardigan + Basic tank + Dressy Joggers + Strap Sandal Heels

Of course there are always variations to be made, and the best strategy is to carry somesort of jacket with you incase the weather turns.

In styling my summer dresses for Fall, I always always always pair them with booties/tennis shoes, usually more utilitarian style combat boots and a leather jacket. I find that in styling the pieces this way they go from ultra feminine to a little edgy and cold weather appropriate.

xoxo Steph

11 thoughts on “Transitioning my Wardrobe From Summer to Fall

  1. I find this time of year a bit difficult to dress properly since it can be warm in the day but become cooler during the evening. I would pair a chunky sweater with some of the stretch pants. Thanks so sharing so many options to choose from!

  2. Trying to find a good outfit during the transition from summer to fall is always a struggle lol. It’s always freezing in the morning and then it gradually gets warm throughout the day. But you can never go wrong with converse and/or a light jacket!

  3. I find it quite strange to read of things happening now which are sort of the opposite to what’s happening here. It is spring here in NZ, but like your autumn’s, it is very changeable. 23 degrees Celsius yesterday, but a couple of days ago it was bitterly cold with fresh snow on the mountains. It certainly makes planning outfits a challenge. Utilising layers is key!

  4. I live in Michigan and have those same issues when the weather is transitioning to Fall. We will have days where we can wear shorts and a tank top, and then the next day need a sweatshirt!I like how you paired the outfits together. Definitely a good idea to dress in layers.

  5. The transition from summer to fall is a tough one here in Atlanta too, because our weather is so unpredictable. Summer fashion is so simple and easy. You can wear basically nothing and be fine lol. But fall is my favorite for fashion… and pumpkin spice lattes! You have some super good go-to’s! Knot sweaters are a must for me in the fall. I’m actually racking up on some this weekend!

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