Transitioning Your Summer Wardrobe To Pre-Fall

As I am writing this, Pumpkin Spice Latte (PSL) season is upon us in ONE DAY… yes people, fall is coming. With that being said, it is sadly time to start putting away the summer clothing and start pulling out the winter wear from the back of our wardrobes. At Hungry and Well Dressed, we are partial to fall…. fall fashion, fashion month, being cozy… the list goes on and on. My favourite part of fall is the very very very beginning through until the weather drops below 10 degrees. After that I’d rather not go outside until Christmas (only to venture to Christmas markets) then escape somewhere warm until all the snow is gone… I’m THAT type of fall girl. Because this is my favourite time of year I want to talk you guys through how I transition my wardrobe and my fall prep!

To commence, I first take a look at all the pieces that I’ve been living in throughout the summer and keep those out. Anything that I haven’t touched, get styled into an outfit to force myself to wear it OR it gets put on “probation” where if it’s not worn next season it gets passed on or resold.

Then, I look at everything that I have from previous fall/winter seasons and see what has been loved, what I like and don’t like etc. things that didn’t get touched all through the previous fall/winter get passed on to make some room.

THEN, here is where the fun begins!

I look through ALL the stores, ALL the websites, ALL the everything fashion related that I frequent. This is to get an idea of the trends, shapes and fabrics that are in this season so I can look through my closet to see what I have that will match or what I want to get to update my wardrobe for the season!

That’s all there is to my process of updating my wardrobe for the season, it’s really straight forward and encompasses steps that most everyone does between seasons or throughout the season anyways 🙂

When it comes to putting together outfits and transitions those for the fall I follow a few steadfast outfit “templates” and I honestly don’t really stray from them. SO… I’m going to share with you my favourite outfits and the way that I put together/ build my transition outfits!


Early Transition Season (Around Labour Day): 

It’s effectively still summer… especially here in Toronto the weather might as well be mid-july… it’s been so hot and humid, which is reflected in my clothing choices.

Nothing much really changes in my choices when compared to summer, however, I do now keep in mind that it’s going to be colder at night so I usually will bring a jean jacket or a light sweater.

The awkward moment in September where it’s too cold to just wear a t-shirt but everything else makes you sweat: 

This is a serious struggle for dressing, because you want to wear long sleeves but any sort of activity makes you SWEAT…

What I try to do in this weather, is stick to light weight knits or long sleeve tees that will still breath when I’m walking around but are heavy enough to keep me warm.

Usually I try to style long sleeves with a skirt, shorts or a dress with a long sleeve layered underneath.

When the Weather is Cool Enough to Wear a Sweater: 

This is the perfect fall time, it’s not too hot and not too cold. It’s the best for fall clothing because it’s not cold enough that you need to throw on the HEAVIEST jacket you own and it’s not so warm that you are going to sweat through your knit wear.

This is when I break out my wool coats, leather jacket and finally jeans (comfortably).

This is the time of year when I begin to wear your quintessential fall outfits. Lots of cozy knitwear with jeans or leather leggings, boots, hats and all the coats!

When the Weather Actually Gets Cold:

This sadly can be the weather from any point in October through to holiday season I’ll wear my normal fall outfits but instead of a leather jacket or a wool coat I unfortunately have to switch to my heavy puffer jacket 🙁

I hope you guys enjoyed this post!

xoxo Steph


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