7 Ways to style summery clothes for cold weather

Oct 29, 2015 at 8:00 a.m. ET
Image: Hero Images/Getty Images

You already know that the number one way to prolong your summer T-shirts, skirts and dresses is by layering them with heavier pieces, which is perfect for those fickle September and October days that start off warm and end up giving you goosebumps.

But we aren't simply suggesting you throw a flannel button-down over a denim romper though, given the popularity of plaid this season, that'll work, too. Here are seven things to keep in mind to transition your breeziest pieces for fall. And as we ease (or crash) into the winter season, add more small layers under these looks and always top with a heavy, comfy, awesome winter coat.

1. Become a layering artist

layer jacket
Image: ModCloth

There's a big difference between throwing any old black sweater over all of your summer dresses and taking the time to truly discover jackets and cardigans that work with individual lighter pieces. "A sweater that you need outside in the morning looks just as good thrown neatly over your shoulders later on," says stylist Gretta Monahan. "But don't do it haphazardly — try the sweater on your shoulders in a mirror to make sure the proportions are right and that the look is neat."

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2. Be selective with colors

Image: ModCloth

Certain summer hues don't work as well with autumn's far less intense light and, for that reason, the easiest transition is to make it play with more sombre colors that fit both seasons. "Ditch the Miami-bright hues in favor of neutrals, and trade the psychedelic swirls for more structural graphics," Monahan says. "The mood of summer is often about a freewheeling vibe, so reining it in a little makes sense."

3. Keep structure in mind

flare jeans
Image: ModCloth

"Pay more attention to fit than in summer months," Monahan says. "Loose or baggy pieces were fine and dandy back in July, but now they spell sloppy." That doesn't mean you shouldn't rock two of fall's hottest pants trends — wide-legged trousers and flared jeans — just be sure they fit well around the waist and hips. Plus, add a structured vest to any T-shirt or tank and hello fall fashion.

4. Find fabrics and cuts that work in cooler weather

plaid skirt
Image: ModCloth

My grandmother always used to complain that women my age and younger were doing themselves a huge disservice by not looking more closely at labels while shopping. Linen and light cotton are lovely for spring and summer dresses, but the cooler temperatures require weightier fabric, like wool, leather or tweed. Adding just one substantial piece to your wardrobe makes all the difference when pairing with a summery T-shirt. "Make medium-weight fabrics your friend," Monahan says. "Ditto sharp cuts and clean-lined silhouettes. Even if you're not quite ready to wear a suit yet, you'll still look pulled together."

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5. Add a camo jacket over a summer dress

Cargo Jacket
Image: Little J Style

Everyone is mixing prints lately — there's absolutely no reason to be intimidated by the thought of trying it yourself. Jackie Welling, a fashion blogger and the creator of Little J Style, suggests layering your cutest summer dress with a cargo jacket and then adding ankle boots and a floppy hat to complete the cool weather look.

6. Wear a turtleneck under your T-shirt

turtleneck t shirt
Image: Little J Style

We're so used to thinking about what we're going to put over our summer clothing to make it weather appropriate that a lot of us forget there's a far more interesting way to layer: Wear a turtleneck (hot fall trend) under your favorite graphic T-shirt — Welling proves it can look super cool (and warm).

7. Wear a summer dress with a long-sleeved button-down shirt

dress long sleeves
Image: Little J Style

Same principle as with the T-shirt: Think about what you can add under your gorgeous sleeveless dress to make it work for the fall — in this case, as Welling shows us, a dressy button-down shirt is perfection.