How to Wear Lilly Pulitzer Over 50

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Lilly Pulitzer is one of those brands that sparks instant joy. The bright colors, playful prints, and effortless resort vibe make it feel like stepping into the sunshine. But if you are over 50, you might be wondering, Can I still pull off Lilly Pulitzer? The answer is a big, bold YES. This iconic brand has been around since the 1960s, and its timeless appeal makes it a great fit for women of all ages. Today, we are chatting all about what makes Lilly Pulitzer such a fun and wearable choice for women over 50, how to style it in a way that feels polished and modern, and a few of my favorite pieces from their latest collection.

LILLY PULITZER CLOTHING FOR WOMEN OVER 50
UPF 50+ Skipper Popover (Large) *more outfits and descriptions below)

We’ve been chatting about a lot of brands for women over 50 lately! You might also like reading about these brands:

Why Lilly Pulitzer Works for Women Over 50

Lilly Pulitzer has been a go-to for resort wear, casual dresses, and everyday fun fashion for decades. But what makes it so great for women over 50?

First, the fabrics are comfortable. A lot of Lilly pieces are made with breathable cotton, linen, and lightweight blends that work well in warm weather. If you’re traveling, heading to the beach, or just running errands in the summer, Lilly has that easy, breezy feel.

Second, the cuts are flattering. Sure, Lilly has some short skirts and youthful designs, but the classic pieces—like the shift dress, maxi dress, and tunic top—work for every age.

And finally, it’s fun! Who says fashion has to be boring just because you’re over 50? Lilly Pulitzer is full of energy and personality. If you love color and prints, there’s no reason to give them up.

How Lilly Pulitzer Has Evolved Over the Years

I’ve always been a Lilly Pulitzer fan, but since I love colorful clothing, that should come as no surprise. If you search for their name on my blog, you’ll find plenty of photos of me wearing their pieces over the years!

FASHION BLOGGER WEARING LILLY PULITZER
ME IN LILLY PULITZER IN 2020

I know many of you think of Lilly Pulitzer and only think of wild prints and bold colors, but it’s time to think again! While the brand stays true to its roots, it has also evolved with more sophisticated styles and modern silhouettes.

Recent collections have introduced:

  • More muted prints – Soft blues (like this stunning collection!), whites, and neutrals alongside the signature brights.
  • Updated silhouettes – Wrap dresses, A-line skirts, and more structured designs.
  • Versatile pieces – Sweaters, blazers, and solid-color dresses that work well beyond vacation wear.

Lilly is still fun and colorful, but now there are even more options for women who love classic style with a touch of personality.

Is Lilly Pulitzer Too Young for Women Over 50?

Let’s get this out of the way: Lilly Pulitzer is not just for 20-year-olds! There are plenty of styles that look elegant and sophisticated on women over 50. The key is choosing pieces that feel chic rather than too young.

A lot of women worry that bold prints can be overwhelming, but the right balance makes all the difference. Some of Lilly’s newer designs incorporate classic elements like tailored fits, softer color palettes, and timeless silhouettes that work for every age.

If you’ve ever hesitated to wear Lilly because you thought it was too youthful, don’t! There are so many ways to wear it with confidence.

Where to Wear Lilly Pulitzer

Lilly Pulitzer isn’t just for vacations (although I do think it’s perfect for that!). It works for all kinds of occasions:

  • Brunch with friends – A shift dress and sandals? One of my favorite outfits!
  • Casual summer days – A tunic top in a cute print with white jeans is an easy go-to.
  • Vacation or cruises – Lilly was made for the beach and beyond.
  • Outdoor parties – A flowy maxi dress looks polished but relaxed.

P.S. Lilly Pulitzer also has great sales, especially the famous Sunshine Sale, where you can grab pieces at huge discounts. If you love Lilly but don’t love the price tags, that’s the time to shop!

My Favorite Lilly Pulitzer Pieces for Women Over 50

LILLY PULITZER FOR WOMEN OVER 50
UPF 50+ Skipper Popover | High Waist Ankle Slim Straight Leg Pants (Size 8) | Italian Leather Soft Loafer (TTS)

This quarter zip pullover c/o of Lilly Pulitzer is one of those pieces that I keep reaching for because it is just so easy to wear! It’s lightweight, super soft, and gives you built-in sun protection, which is always a plus. The bright pink print has little hearts, which makes it so fun without feeling over the top.

I bought the Lilly Cane Tote years ago, and it is still one I carry every summer. They have a couple of smaller similar cane handbags on their website that would work great for summer.

SKIPPER POPOVER
UPF 50+ Skipper Popover

I love a top that can do it all! You can layer this one with workout clothes on your way to the gym, wear it to the golf course or pickleball court to protect your arms from the sun or pair it with leggings and slip-on sneakers for those days when comfort is the priority. I threw it on with white jeans for an easy daytime look that is perfect for brunch with the girls or a casual shopping trip. It is effortless, cute, and so easy to style!

RED OUTFIT STYLED ON WOMAN OVER 50
KAYCEE SWEATER | LESIA BUTTON DOWN SHIRT

I bet you’d never guess this outfit came from Lilly Pulitzer! When Lilly Pulitzer gifted me this classic V-neck sweater, I knew it would be a timeless addition to my closet. I paired it with their relaxed button-down top, and I love how the striped collar and hem peek out, adding just the right amount of personality. The mix of textures and patterns keeps it interesting while still feeling effortlessly polished!

LILLY PULITZER OUTFIT SWEATER AND BUTTON DOWN SHIRT
KAYCEE SWEATER | LESIA BUTTON DOWN SHIRT | Super-Soft Flare Jeans (Size .05) | Bit Soft Sole Nappa Loafers (TTS)

I styled it casually with jeans, but this combo could just as easily be dressed up for the office or church. Swap the denim out for a pair of tailored trousers or sleek ponte pants, and you have a polished, work-friendly look that’s both comfortable and chic. Add a structured blazer for extra sophistication, or keep it simple with classic loafers.

LILLY PULITZER QUILTED ELENI PULLOVER LIGHT PINK
ELENI PULLOVER (Large)| The Hustler Ankle Jeans (Size 29 – A Little Tight)

The Eleni Pullover c/o of Lilly Pulitzer is the perfect mix of cozy and cute, and I love this soft pink color! The quilted fabric gives it just the right amount of texture, making it feel a little more elevated than your average pullover. And can we talk about that gold half-zip? Such a fun little detail that adds a touch of polish without trying too hard.

HOW TO WEAR LILLY PULITZER AS A WOMAN OVER 50
ELENI PULLOVER

This is one of those outfits that’s as comfy as it is stylish. It’s got a relaxed fit, but it still looks put-together. I paired it with jeans here, but it would be just as adorable with joggers and sneakers. Lilly always knows how to make casual feel a little more special, and this pullover is a perfect example of that!

Shop Lilly Pulitzer:

So, what do you think? Do you wear Lilly Pulitzer? Let me know in the comments. I’d love to hear how you feel about this brand!

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Verse Of The Day

Titus 2:11-12 NIV
11 For the grace of God has appeared that offers salvation to all people. 12 It teaches us to say “No” to ungodliness and worldly passions, and to live self-controlled, upright and godly lives in this present age,

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189 Comments

  1. Found it.
    Beautiful pinks and blue.

  2. Yes, I love Lily Pulitzer too.
    I only started wearing them when we moved to FL 4 years ago.
    I’m 72 and it makes me happy when I wear Lily.

    Thank you for posting about thus fun brand.

  3. Connie Ritchie says:

    found it! Very tricky!

  4. Found it! I love the bright colors and prints of Lilly Pulitzer!

  5. Deborah Torres says:

    Finally found it!

  6. Found it!

    I bought a Lily top you styled a couple yrs ago when I first started following you. It’s still in my dresser never worn. Hopefully this will be the year I get to take it out and wear it.

    1. Get it out and wear it!!!

  7. Dawnine Hillman says:

    Found it 😀

  8. Danielle Ponto says:

    Found it! I have always loved the bright happy colors of Lily Pulitzer! I own a few tops plus a beach cover-up. Wearing them brightens my day.

  9. Found it! My daughter’s love Lily Pulitzer.

  10. Didn’t find it! Pretty pink!

  11. Dorothy Kennedy says:

    Found it! Love the Lilly Pulitzer and the pop of bright colors!

  12. Found it! Love all the colours of her design for summer!

  13. Leslie Daulton says:

    found it!! love the textured print on the pink eleni pullover.

  14. Found it….that was difficult to find

  15. Found it!
    Been a Lilly fan since my 20’s. 🌴

  16. Julie Feagins says:

    found it
    Where will I find your “what I have on order” page when it is not hi-lighted in the intro?

  17. Susan Riley says:

    Found it! Cute and colorful styles on you.

  18. Found it!
    Love Lily P. !

  19. Found it. I think the Lily colors are so flattering.

  20. Found it!

    I absolutely love Lilly Pulitzer! I really like the bright color patterns.

  21. Linda Shearer says:

    Found it.

    The Lily Pulitzer looks so comfortable!

  22. Found it! Love the maxi dress…

  23. Kim Martin says:

    Found it! I love the pink pop over!!

  24. Pam Baker says:

    Found it and LOVE Lilly!

  25. Julie Olsen says:

    Found it. I love the pink top!

  26. I love Lily! We try to cruise at least once a year and we have a second home on the SC coast. I have a few Lily pieces, many found at TJMaxx or Marshalls, for a great price. Fun pieces.

  27. I got so involved looking at these lovely pieces, I missed icon. I had to go back to look, and finally FOUND IT!

    1. Persistence pays off! Lol!

  28. Found it
    I love the pink popover

  29. Roberta Schwandner says:

    Found it!

  30. Found it! Love the dress and the 1/4 zip tops. Seem to wear the 1/4 zip tops in the winter

  31. FOUND IT🙂! I love the pink quilted pullover! The color is beautiful

  32. Christina Kuehn says:

    Great items. I found it! Love the one shoulder dress.

  33. Christina Kuehn says:

    I found it! Love the one shoulder dress.

  34. Found it. Love the pink pullover on you, Tania.

  35. Carol Ann Jablonski says:

    FOUND IT

  36. Found It! Love the pink tops on you. Valentine’s Day and Spring must haves.

  37. Pam Bowling says:

    Found it!
    I have worn LP on vacation and on summer days. I LOVE the pieces you showed us today. You looked great in them.

    1. I love LP, and I really like these items that aren’t the traditional print we associate with LP.

  38. Found it! Love the pink pullover.

  39. Gay Manning says:

    Great looking outfits!

  40. Paula Presbrey says:

    I found it !
    Loving the bold colors !

  41. Wendy Hoff says:

    Found it! Cute styles!

  42. Found it! Love this post!