You don’t see Lilly Pulitzer much in San Francisco, if at all. It seems to remain a staple for towns with preppier roots. Growing up on the east coast, I still have at least two Lilly dresses in my wardrobe (plus an archive of many more at my parents house in Florida). I rarely wear them but once in a while I find one I really like and get it.
Over the last decade, I’ve become a lot less preppy. My early 20s were very preppy. But as I’ve gotten older, I now lean towards a mix of simplicity and vintage whimsy. Yet, some traces of those preppy roots have stuck with me.
I’ve always loved the original Lilly Pulitzer photos from when she first started making her dresses in the 50s. So, this past year as I’ve really leaned into 50s and 60s vintage to inspire my everyday style, it dawned on me to use these vintage photos to give new life into my Lilly dresses I never wear but still very much love.
(Also, this is not a sponsored post, just some thoughts on style ideas for something that lives outside of your style aesthetic but something you still want to wear.)
So here are three ways I’ve been wearing a usually preppy dress in less preppy feeling ways!
What better way to create a vintage inspired look than to add some actual vintage. This 60s lace jacket came with its matching shift dress in the same color (one of my favorites!) which happens to perfectly pair with the blue of this Lilly Pulitzer dress. I found a similar one here in a gorgeous light green color.
I added a more modern and simple block heel. Mine are old but this similar pair is so cute.
For this outfit, an easy clog felt less predictable but still simple and more minimalist. Then a summery straw hat and shell necklace for a whimsical touch. It feels here more like a vintage printed shift despite being new.
A silk scarf as a belt is a great way to break up the busy, bright patterns. And a beach-y huarache for a more masculine touch. Bringing down the super girly-ness of the pattern.
From what I’ve been trying out, it seems a non-traditionally preppy shoe and more bold, playful accessories make all the difference. Like a good leather huarache and a simple silk scarf. I still love a pair of Jack Rogers with Lilly Pulitzer dresses on occasion, but now I prefer a more vintage, quirky approach!
Which style is your favorite?
Mary
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