Southern Belle in Training

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

June 21, 2019

National Wear Your Lilly Day 2019!

     Happy first day of summer, and more importantly happy National Wear Your Lilly Day to my fellow Lilly Pulitzer lovers! This is a holiday that I love to commemorate every year with a blog post, and I'm so excited to share this year's outfit with you. These pictures were taken by my photographer Kate in the vines at King Family Vineyards, which is my favorite local vineyard. It seemed very fitting to combine my love of Lilly Pulitzer with my love of Central Virginia Wineries!

Photography by Kate Greer

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     For this year's National Wear Your Lilly Day post I'm actually proudly wearing a secondhand Lilly find! There is a wonderful upscale consignment boutique in downtown Charlottesville called Darling. I've been consigning clothing with them at the end of each season for about a year now, and on my last trip in to drop off some spring clothes to sell, I found and fell in love with this gorgeous Lilly dress! It was priced under $50 and in wonderful condition, so I knew it had to come home with me. I learned thanks to a Lilly lovers group on Facebook that the print is In the Via (in the lighter blue option) and the style is the Brielle dress. 

     This dress is work appropriate for my job, and I'd also wear it to church or for other fun weekend events... like visiting wineries. 😉I haven't owned any Lilly dresses in the Brielle style before, but I like this one! It is doubly lined and the fabric is quite thick- so I do think this would be a better dress for spring or early fall instead of the middle of summer. 

    Kate and I took these photos at King Family Vineyards- which is my favorite winery that I've been to on the Monticello Wine Trail! I review all the ones that I visit (blog posts for wineries can be found on my Travel Guides page), but I surprisingly haven't written a review for King yet- that's going to change this summer. Their wines are my favorite, and the views here just can't be beat. So it was extra fun to shoot the look for this year's National Wear Your Lilly Day at one of my favorite local places!

     I love celebrating National Wear Your Lilly Day each year both in person and on the blog! Lilly Pulitzer is one of my favorite brands, and there is a special camaraderie that comes with finding other Lilly fans. Through blogging, it's been so fun over the years to connect with other Lilly lovers around the country, and even get to do a couple blog collaborations with Pink Colony, a specialty boutique that sells Lilly in Vermont! I've been wearing Lilly since my freshman year of college (which is also when I started this blog), but I didn't start doing National Wear Your Lilly Day posts until 2015. Here are my posts from past years:
     Fellow Lilly lovers: I'd love to know what Lilly you're rocking today!! I was going to wear the outfit in this blog post to work today as well, but at the last minute I decided to go with white jeans and an Elsa top for today! And of course my beloved Lilly travel mug.

     God Bless,

     xoxo Annaliese 



  1. It's the happiest day of the year in my opinion ;) Love seeing everyone's color and print coming out to play! Happy #NWYLD!

  2. I totally didn’t know this was a thing! Well I guess I know what I’m wearing today !;)

  3. I love celebrating summer this way! I love your print too!

  4. This dress looks so cute on you, Annaliese! I wore a tank dress in Stuffed Shells for NWYLD as I was nannying and didn't want to wear anything too crazy haha!


  5. You look so beautiful! I love this holiday so much and Love to get Lilly secondhand too. Vintage Lilly is always my favorite.


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