Transitioning Your Summer Wardrobe into Fall

October in Chicago is always a toss up. Sometimes, we’ll get chilly winds and snow. Other times, we’ll get unseasonably warm fall weather… (Sometimes it’s even in the seventies like it’s been for the past few days!) With this constantly fluctuating range of temperatures, transitioning a wardrobe from summer to fall can be a bit difficult. This outfit is a solid example of how I transition summer pieces and trends into a fall outfit.

What I Wore

Cupcakes & Cashmere Off-the-Shoulder Sweater – Cropped Skinny Jeans – Bronze Sandals – Y-Necklace – Rose Gold Bangles – Black Drusy Cocktail Ring – Timex Chronograph Watch – Gold Mica Earrings – David Yurman “X” Bangle – Marc by Marc Jacobs Bag (Similar) – Rose Gold Ring

One of the trends that was very “in” this summer was the off-the-shoulder top. This Cupcakes and Cashmere sweater is a perfect way to bring this trend into the next season. It still (obviously) has the off-the-shoulder look, but it’s also a sweater, so you get the best of both worlds! I think that in addition to pairing well with jeans, this sweater would be super cute with a skirt or a pair of denim shorts for one of those surprise “hot” fall days.

I live in my Jacks during the spring and summer, so it’s always hard to put them away for the colder months. One of the things I especially like about Jack Rogers sandals is the fact that they come in a wide multitude of colors. These bronze ones are no longer sold, but there are so many pretty hues to choose from that will work for both summer and the warmer portion of fall. These brown ones would be perfect with transitional outfits!