Spring

Chic Florida Outfits from Lilly Pulitzer for Women Over 40

Florida is a top vacation destination for many of us who live up north, including my husband and me. We’re back and forth all the time, which means I always like to have some cute Florida outfits hanging in my closet and ready to go. One brand I can always count on to look pretty, colorful, and chic down south is Lilly Pulitzer.

I’m a big fan of her light, cheery designs, which are perfect for gals over 40, 50, and 60 who love playful resort wear. I was recently in Florida and picked up a lot of cute new things, which I also plan to wear back home this summer. Have a look at these darling finds that make vacations and summer a whole lot more stylish and fun!

Chic Florida Outfits from Lilly Pulitzer 

Florida Outfits from Lily Pulitzer

Linen Pants | Sweater | sandals | bag

Linen Pants and Sweater

You can never go wrong with linen pants and a beautiful breezy sweater. Lily’s linen pants are lined, which is a rare find, and they fit beautifully. I sized up one from a small to a medium just to achieve a looser, beachy look. The sweater is a stunning green creme de menthe color, and I love the beachy rolled neckline and hem. Talk about the perfect beach outfit!

 

 

Green Striped beach Dress

Green Striped Beach Dress

 

Cute Beach Dress

Now, this is different! I wasn’t sure about this little number until I tried it on, but I instantly fell in love with it. This striped polo beach dress has a perky look and feel, but it’s also very feminine. Do you see the ruffled neckline, which adds a touch of romance? It’s really quite different. This dress seemed short on the hanger, and yes, it is. It’s a sundress, so it’s meant to be worn with flats, but I found that when I got it on, the longer sleeves made it seem much more modest and easy to wear. It’s become one of my favorite vacation dresses!

 

Eyelet Dress Florida outfits

Eyelet Dress | Gold Sandals | Earrings

Eyelet Dress

This dress knocked me out, and I had to have it. I love the intricate eyelet detail and the gorgeous ladylike feel of this dress. It’s a shirtdress style, making it very easy to wear and also very versatile. When you want to dress up a little but still look relaxed, this is the dress to wear. And don’t get me started on that stunning shade of blue. It’s a pretty yet practical dress that would also be great for a bridal shower, baby shower, or even graduation.

 

Blue Waist Tie A-line Dress

Blue Waist Tie A-line Dress | sandals

Blue Print Dress

If there is one thing Lilly Pulitzer is known for, it is prints – busy, bold, wild prints that put a smile on your face and a pep in your step! I love this blue tropical print sundress. It’s soft and silky, and the long sleeves are a rare find. You can wear it loose or belt it, and with a cute pair of sandals, you have the perfect outfit for a dinner date!

 

 

Red Sweater Dress Florida Outfits

Red Sweater Dress | sandals

Red Sweater Dress

Have you ever been on vacation and been surprised when it got in the evening, or perhaps you just had a few cool days? That happened to me when I visited Sarasota in February, and they were experiencing a cold spell. This cute vacation sundress would have been perfect for that. It’s short and sporty, and you can wear it with flats, but it is also knitted with warm sleeves to keep you cozy. I love the tropical red, too!

Related: What To Pack For Florida: 7 Breezy Vacation Outfits

 

Pink and White Tunic Dress

Pink and White Tunic Dress | sandals

Tunic Dress

One thing is certain: if you want to stay cool in the heat, a loose-fitting tunic dress like this is ideal. I love the deep V-neckline and the ultra-feminine sleeves. Do you see the subtle pleating in the front that pulls the dress in and gives it shape so it doesn’t look frumpy?

 

Pajama set

Pajama Top | Pajama Bottoms | Sherpa Slides

Pajamas

I couldn’t resist! Lily’s colorful PJs are incredibly cute and ultra-comfortable. I love these. They are soft and comfortable, and that bold print makes me feel happy about waking up!

If you’ve never worn Lilly Pulitzer and are looking for cute resort wear for summer, you can’t go wrong with this brand. Lilly Pulitzer is a brand that embodies a relaxed, colorful, and chic aesthetic. And the quality is fantastic. See you in Florida, on the beach!

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Meet the author

Deborah Boland

Deborah, a former Fashion & Lifestyle TV host and Image Consultant, understands the style challenges women face in their 40s, 50s, and 60s. As the founder of Fabulous After 40, she helps women tweak their chic and embrace fashion with confidence—so they always look and feel amazing.

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