Fashion 101: Transitioning to Fall

We’re almost halfway through October (wait, really?) and fall weather is officially here. If you’ve been keeping up with my blog, you know how much I love this season and the fashion that comes with it. We’re all familiar with the obvious autumn staples: chunky sweaters, leather boots, infinity scarves — the list goes on and on. But have you ever considered pulling a few of your summer favorites out of hibernation and incorporating them into your fall looks?

Modifying spring and summer pieces into autumn-appropriate ensembles is one of the easiest and most fun ways to freshen up your wardrobe — not to mention create tons of new outfits. For this little fashion 101 lesson, I chose three spring/summer essentials and made simple modifications to effortlessly transition them into the cooler months. The three staples I chose were: the maxi dress/skirt, a gingham button down (or any warm weather blouse, really), and the summer sundress.

To create these ensembles, focus primarily on your new favorite fall fashion vocabulary word: layering. By adding a cable knit sweater, a scarf, a denim jacket, a blazer, a fur vest, leather boots — the list goes on — you can easily transition your summer staple into a cozy fall look. Check out my ideas below!

Maxi Dress/Skirt
With your summer maxi dresses and skirts, the first thing you want to do is throw on a chunky sweater or substantial long sleeve shirt. You can either leave it at this, or add a scarf for optimal coziness — I’d opt for one in a warm autumn hue if you need a pop of color, or perhaps a leopard scarf if you want to get into print mixing. Then top off the look with some ankle boots or oxford flats and you’re good to go!
striped maxi   |   cable knit sweater   |   utility boots   |   crossbody bag

Gingham Shirt
Take your go-to spring & summer shirt, whether it’s gingham, plaid, chambray or floral, and get to layering. You could go for a breezy look and leave your blouse unbuttoned with a tee underneath, or opt for a more put together outfit and layer a shirt or sweater on top of your blouse and let the collar peek out. My favorite look, however, is to slip on your cuddly fur vest to instantly autumn it up (I guess I just turned my favorite season into a verb — someone stop me). To finish off this look, grab a knit infinity scarf, dark jeans and boots, and you have an instant chilly day outfit.
gingham shirt   |   fur vest   |   jean leggings   |   harness boots   |   tube scarf   |   mustard clutch

Summer Sundress
One of the trickier pieces to transition to fall is your favorite summer sundress. It’s only tricky because a lot of people can’t fathom wearing their floral tank dress in October — but worry no more, because this year floral has transitioned into one of the biggest fall prints. To easily execute this outfit, opt for a cardigan or blazer to start out. If it’s extra chilly, you can layer a denim jacket on top of your cardigan and wrap on a scarf. As for the bottom half, slip into some tights and ankle boots or oxfords, or even layer on some fall socks (pictured above). As for me, I love how the ensemble looks with over the knee boots and black thigh high socks peeking over (not pictured). y-4
floral dress   |   mustard cardigan   |   denim jacket   |   over the knee boot   |   gem necklace

Would you try out these looks? If you do try a tip from this fashion 101 lesson, email me pictures at and you could be featured on my blog!

(image source:,,,,, pinterest)

9 thoughts on “Fashion 101: Transitioning to Fall

  1. Pingback: Menswear-inspired layering | Librarian for Life and Style

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