Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

October 30, 2017

How to Wear Lilly Pulitzer in the Fall.

     It's no secret that I'm a big fan of the Lilly Pulitzer, and the iconic bright colors and preppy styles that has made the brand famous. Of course my love for Lilly does intensify a bit during the warmer months, but it doesn't mean that I stop loving Lilly in the fall and winter!! Today I'll be sharing a fall-appropriate Lilly outfit, and a few tips that I use when putting together preppy looks to keep my Lilly love going strong all year long (even here in Vermont!).

How to Wear Lilly Pulitzer in Fall

Lilly Pulitzer in Fall

Fall Preppy Style - Lilly Pulitzer

Stowe Vermont - Preppy Fall Style

Tory Burch Riding Boots Lilly Pulitzer

Stowe Vermont Fall Foliage

Vermont Fall Style

Photography by Melissa Lynn Studios 

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     Lilly Pulitzer can absolutely be worn in the fall, and even some pieces in the winter months!! As long as it's the right Lilly items. The main reason that I ordered the day dress that I'm wearing in today's post is because I knew it was the perfect Lilly dress to transition from summer to fall. The navy stripes and purple design on it are a bit of a contrast from some of the pinks, greens, and bright neon hues that are present in a lot of Lilly's summer shift designs. It was so easy to make this outfit ideal for fall by adding a vest and riding boots! If looking for Lilly dresses to wear in the cooler months, look for ones that might be short sleeved or have 3/4 length sleeves like this one did, and in darker colors than Lilly's traditional summer color palette. 

      Other Lilly items that I enjoy wearing in the cooler months are scarves, athleisure (I adore my workout leggings that I have!), and Elsa tops. A bright Elsa top is a great way to add a pop of color to a fall or winter business casual look. I don't personally own any Lilly Pulitzer sweaters yet, but I do know that they make some gorgeous sweater and cardigan options as well! 

     And of course I can't forget... the best way to add a pop of Lilly to your look during fall and winter is to bring a Lilly travel mug with you for your hot beverage! I bought my Lilly travel mug during freshman or sophomore year of college, I still use it multiple times a week, and it's held up so well!! I want to ask for another one for Christmas this year since I use my first one so much. 

     Today's outfit post is the last of my Stowe, Vermont photoshoots with my photographer Melissa! We did a Stowe day trip a few weeks back, and were able to get some really fun photoshoots in (this post, this post, and this post were also done that day!!). Unfortunately we were there a few days before the foliage really started to turn, but I was still happy to spend an afternoon there shooting! Stowe is a very quaint little resort town deep in the Green Mountains of Vermont. It's about an hour south of Burlington, and although it's very drivable for a day trip, I think it feels much further away! Just from browsing my Instagram and Blog Lovin' this fall season, it seems like a lot of bloggers from all over the country have been vacationing in Stowe during foliage season. I think Stowe would be a cute place to visit if you're unfamiliar with New England and want a taste of small town life for a few days! 

     God Bless,

     xoxo Annaliese 



  1. Your outfit is adorable! I love how you can transition summer & fall things. It's like my wardrobe doubles in the winter!

  2. You are too cute! I absolutely am obsessed with those boots & love the look you've put together.

  3. So cute! You nailed it. Love me some Lilly P!

  4. Love the transition look! I totally want to come to VT and see the fall foliage at some point in my life.

  5. I brought my lily mug to school the other day! All the kids loved it!!

  6. This is SO cute! I'll admit I've never really worn my Lilly in the fall but now I'm totally thinking I should - this is adorable!

  7. Love this dress and I really like how you styled it!

  8. So true! The right Lilly piece is essential! Love it with the boots.

  9. What a cute outfit! I love LP but I always feel it is so hard to wear in the fall.

    xoxo, Paige

  10. I haven't bought anything LP in a while. You look so gorgeous! Almost makes me want to go buy something to wear this fall!

  11. Girlfriend, I just absolutely adore these pictures of you!

  12. Your outfit is so adorable! I can't wait to see how you do winter pieces for the real New England winters!

  13. In my mind bright colors and patterns have always been appropriate year-round, but I agree that it can be a delicate balance and there's a RIGHT way to wear something as statement making as Lily in the colder months!

  14. Love this outfit on you, Annaliese! I wear my Lilly year round haha, I can't bring myself to put it away!



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