Fashion Moments

An Outfit of the Day Moment – How to Wear Lilly Pulitzer in Fall and Winter 2016

Hi everyone!


Outfit Details: Dress (Similar) / Vest / Boots (Similar) / Earrings

Some of my After Party Sale purchases areĀ still on its way. I have one straggler left. But I am so, so happy with everything else that I’ve received so far! It was definitely a success.


This is one of my favorite dresses because I can style this so many ways going into fall and winter. I did a post last year around this time onĀ how to style Lilly Pulitzer for the cooler seasons, and I worse this same vest there, too. Vests are a great option for adding warmth to you Lilly because they’re cute without overwhelming the outfit.



This vest I actually grabbed off of Etsy, but there’s an identical version on J. Crew Factory’s website right now, and I’d go with that one. Herringbone vests are kind of an iconic “preppy” staple, especially in a fall and winter wardrobe. I would say they’re worth the investment because, like a nice neutral navy and white Lilly dress, they can be worn with pretty much anything. It goes so well with plaid, and I’ve even worn it with leopard print.



Riding boots are a no-brainer. When the temperatures really drop, add a pair of black tights or even some nice knee-high, cable-knit socks. Pop on some classic pearls, and you’ve got yourself a wonderful fall outfit.


I kind of feel like I should be going to ride a horse or something while wearing this, but I’m into it lol. I wish I knew how to ride a horse. This is one of those outfits where I definitely look like I live about five states down from where I actually do. Like I’ve always said, I’m a little more Palm Beach than Pittsburgh when it comes to my clothes.


Thanks for reading everyone!

xoxo Rebekah

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