1. Peter Pan Collar

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This look is classic, and can be dressed up or down. For a night on the town, some sleek black jeans amp up the drama. For brunch with the gals, denim cutoffs make this casual and cute.

2. Circle Skirt

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Whether long or short, a circle skirt is guaranteed to give your outfit some sass and flare. A shorter circle skirt is great for the spring, and longer for the fall. The fuller body and folds of fabric look and feel luxurious and stylish!

3. Turtle Neck Sweater

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Channel your inner artist with a classic black, or add your own flare with a color or tank sleeves—whatever the specs, a turtleneck sweater is classic and can be balanced by a shorter skirt or slim jeans.

4. Wind Breaker

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Whether you’re bold enough to try a crazy vintage print or you just like the loose look and elastic waist, a 90’s windbreaker is a statement piece with surprising warmth. I love my dark teal windbreaker (goodwill!) and it keeps me warm in the fall, the spring, and even some milder winter days.

High-Waisted Jeans or Shorts

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These were normal back in the eighties—after the low-rise craze of the early 2000’s, they’ve earned their own name on the shelf. High-waisted jeans (or high-waisted anything) are so flattering and, frankly, more comfortable than jeans you have to hoist over your butt all day. And personally, I’m super excited that the fitted-waist loose-leg Levi’s look is back from the 70’s. High-waist all the way.