Fashion Moments

A What to Wear Moment – Styling Lilly Pulitzer for Winter

Hi everyone! We are a short nine days away from Christmas (can you believe it?), but it really doesn’t feel like it.

At least here in Pittsburgh, temperatures have been in the 50s and 60s, which is very unusual for this time of year. The warmer weather has me dreaming of summer, when I was able to romp around in my bright Lilly Pulitzer shorts and dresses without freezing to death.

But just because it will be winter eventually doesn’t mean that I have to stow away my Palm Beach pieces for the season. And neither do you! After all, it was Lilly herself who said, “Despite the forecast, live like it’s Spring.”

Here are a couple of outfit ideas that I put together for wearing your Lilly Pulitzer during the winter. It’s all about layering, and don’t forget to top each outfit off with your favorite winter coat and accessories. I hope you enjoy!

Look One



This is one of my absolute favorite Lilly dresses that I own. It’s in the pattern Paws Off from last fall, and I snagged it during the winter After Party Sale. To make this cotton dress more appropriate for winter though, I added a herringbone vest, black tights, and riding boots. I got my vest, which has heavily-padded quilting for warmth, off of Etsy. It’s inspired by the (very expensive) J Crew vests from previous years. This one was less than $40, though, which is awesome.

Look Two


This skirt I’ve only had the opportunity to wear once since I got it at this summer’s After Party Sale. It’s the Tate skirt in Bay Blue Coasting Engineered. This one is super summery, with pretty coral and shells intertwined with the pattern. You can easily tone down the beachy vibe though with tights, boots, a long duster cardigan, and a black top. The skirt will add a pop of color, but keeping the rest of the outfit dark and understated means that you can rock this all throughout the winter months.

Look Three


This outfit oddly reminds me of something that Taylor Swift might have worn back in the day. I love how bright and fun this one is – it perfectly embodies palm beach while still being appropriate for Northeastern weather. It’s flowy, fun, and super comfortable. I paired the silk Maisy dress with a floating white sweater, black tights, and the same pair of riding boots. This is the perfect outfit for when you want a punch of color to spice up those dull, cloudy winter days (that happen 99 percent of the time in Pittsburgh).

Thanks for reading!

xoxo Rebekah

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