My Favorite Lilly Dresses + Your Guide to Shopping Lilly

You guys probably don’t know this about me, but I’m obsessed with Lilly Pulitzer.

(I know. I’ve never mentioned.)

My friend MaryBeth introduced me to the bright, whimsical dresses more than 10 years ago when I was in college, she’d just graduated from Tulane, and was way too cool for me. I wanted to hang with her and her friends, and I bought my first shift and haven’t looked back.

I even interviewed for a job there a few years ago. It didn’t work out, but I kind of love my job now, so it’s fine. 

Anyway, the more I’ve written about Lilly dresses, the more I’ve gotten questions from you guys (slash my friends also consider me the resident Lilly fit expert), so I thought I’d share with you in the spirt of #NationalWearYourLillyDay

National Wear Your Lilly Day

Just for funsies, here’s a few of my favorites over the past few years.

But for reals tips on how to find the right fit:

Let me caveat this that I generally consider my body curvy/athletic. Even at smaller sizes, I still have boobs and hips, so most of my fit notes are from that perspective.

Length: I’m lucky to be a very average 5’5”, but some of my taller friends definitely complain about the length. If you are taller and work in a more conservative office, these dresses may not be for you.

Chest: Honestly, I think these dresses are cut for younger women, or women who aren’t as busty. I have been every size from 2 (ok, once) to 12 over the past 10 years, and the chest has always been the most difficult part for me to fit. The Richelle strapless dresses will never fit me.

Stomach: Some of their dresses are a much tighter fit than others. While beautiful, the Alexa High Collar style (one of the recent basics) will never fit me well. Same with the Cathy shift dress.

My bottom lines: if you’re looking for a slightly more forgiving cut, here’s my current favorites: 

Annabelle Shift Dress | Jacqueline A-Line Shift Dress | Sloane V-Neck Maxi

I’ll also add that if you can get your hands on any of the LP4T stuff, the shifts were cut really generously AND include a little spandex in ‘em. 

Any other fellow Lilly lovers out there? What’s your favorite cut/print?

Let's Cha Cha

Let’s Cha Cha will always be my favorite, and what I have on my iPhone/iPad…

In the Beginning Lilly Pulitzer

In The Beginning is another really cool one — it tells the story of the brand through a print. I have this on a makeup bag (and a dress that doesn’t currently fit, boo) and it makes me happy every time I use it.

10 comments on “My Favorite Lilly Dresses + Your Guide to Shopping Lilly

  1. Danielle

    How does the recent kerfuffle over those fat shaming pictures in a staffer’s cube change your view of LP, if it does at all? I’ve seen some people returned their Lilly for Target stuff and won’t wear their originals anymore. There’s something off-putting about a company environment where that was considered okay to post in your public space. I know I’d feel strange supporting a company where people felt fine posting a racist or sexist cartoon like it was NBD. I dunno, I had a neutral opinion of Lilly stuff before, but I’m certainly hesitant now.

    1. Theodora Blanchfield Post author

      I wrote some about it here: Neither of us know the whole story about that employee, though. There’s obviously more than meets the eye – who knows how depressed she is/was/what she’s struggling with? I’d have to think nobody else saw/noticed it — or at least not anyone working on this story – before this. It absolutely does leave a bad taste in my mouth, though I honestly can’t say enough that I’ll stop wearing half my wardrobe.

  2. Becky @ Olives n Wine

    Now that I live in SW Florida, I feel like I NEED at least one Lilly dress (or five…) 😉 I told myself I’d have one by the end of the summer so this is super helpful! Sounds like I’ll be glad I’m on the shorter side but will have to be cautious in the curves department. A ton of boutiques carry Lilly here in Naples so I’m happy I’ll be able to try on styles before purchasing!

  3. Mary

    Yup. Love Lilly. Grew up on Martha’s Vineyard, that was a requisite purchase every summer! (okay, a couple of purchases….)

    I’m about to say the most stuck up sentence… sigh…. Now that I don’t have my dad’s credit card (for many years now! just saying…), AND I live in Los Angeles, Lilly shifts don’t QUITE fit in here. (Plus working on Skid Row in downtown LA doesn’t really work with Lilly attire either….) so now I lean more towards accessories and things like that.


Leave a comment

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.