Wear Now, Wear Later: How to Transition Your Summer Pencil Skirts into Fall

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A few years ago, during a particularly hot summer, I discovered stretchy pencil skirts and my life was changed forever. They are the perfect bottom to wear during a hot summer day; they have enough coverage, allow for breeze on your legs, come in a ton of cute patterns, and they go with pretty much everything. They’re also amazing when you’re pregnant since they’re super stretchy!

After wearing them all summer, you might think I’d be sick of them, but no. I love them so much that I want to wear them all year long, and luckily they’re super easy to transition into fall. So they’re a great “Wear Now, Wear Later” piece.


During the summer, I love wearing my pencil skirts with a graphic tee. It instantly dresses it down and is the same feel as a tee and shorts, but just a little more interesting and unexpected. Pull your hair off your neck and grab a pair of sandals and you’ll be the cutest soccer mom out there.


Tee from Little Adi, $28 // Similar pencil skirt from Old Navy, $24.94 // Similar sandals from Go Jane, $16.90 // Bag from Lily Jade, $275

As we move toward fall and the weather cools down, it’s time to pull out the layers. A chambray is a staple for me during the fall, and it’s a good neutral layering piece, especially when your skirt has a bold pattern. I threw on a camo print jacket to complete the look, but on the warmer fall days, you can pull it off and tie it around your waist. I also paired it with ankle boots (which works as long as your skirt hem is above your kneecap — check out my post about that here) and a quilted crossbody bag.


Camouflage jacket from Old Navy, $24.97 // Chambray shirt from Old Navy, $18 // Sam Edelman boots from Nordstrom, $159 // Similar bag from Nordstrom, $28

Floral pencil skirts are definitely perfect for summer but can also be transitioned to fall with the right accessories. Pull warmer fall tones in with your shoes, bag, and a scarf, and neutralize everything with a simple chambray shirt. The open toed shoes will keep you from overheating, but the scarf will help your outfit look season-appropriate!


Similar chambray shirt from Old Navy, $18 // Similar scarf from Old Navy, $18.94 // Similar skirt from ASOS, $26.66 

Puffer vests are one of the best layers for fall since they’re warm but not as stifling as a full coat. Plus, they’re just fun layering pieces. I typically wear mine with jeans and a flannel or something, but pairing it with a blouse and a pencil skirt is a fun and unexpected option for fall. Throw on a pair of tights for those cooler days, and style it with a pair of Mary Jane wedges, like I did, or some boots!


Similar puffer vest from Zappos, $198 // Similar blouse from Forever 21, $17.80 // Similar tights from We Love Colors, $13 // Similar pencil skirt from ModCloth, $29.99

How are you wearing your summer pencil skirts for fall?


Find more of Merrick’s style and writing at Merrick’s Art

You can also find her on Instagram and Twitter

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