Looking Back at My Lilly Pulitzer Looks Over The Years

I’ve worn Lilly Pulitzer clothing my entire life, and I feel like the brand that sparked my desire to blog to share my outfits and travels is more of an old friend than a clothing company. Some of my happiest moments in life happened while I was wearing Lilly Pulitzer clothing, like when I found out I was accepted to U of M when I graduated, our engagement, the first day of new jobs and internships, charity events, and of course some of my favorite travel memories happened while I was wearing Lilly. Whenever I need something fun, colorful, and cheerful, I always turn to Lilly Pulitzer, and like any dependable friend, they always have exactly what I need. Here are some of my favorite Lilly Pulitzer looks that I’ve worn over the years.

Back when my blog name & Instagram were both @LillyLovingPrep (yes, I was and still am that obsessed with the brand, haha), I accidentally matched with the dressing room wallpaper at my local Lilly store while visiting to try on their latest drop. I particularly love this sailboat print “You Gotta Regatta” because it was inspired by the regatta that happens every year near my hometown of Petoskey, Michigan! This is the Lynnie skirt.

I told you I loved this print! I owned every YGR item ever made at one point, although they rereleased this print due to its incredible popularity after a few years. At that point, I didn’t keep up on it as much because I liked the original a bit better, and I didn’t need duplicate items in the different iterations of the print. This photo was taken the first morning of our first stay together at Grand Hotel on Mackinac Island, right after we were married. This is the Treena maxi.

I took this mirror selfie before heading out to an amazing brunch with some of my friends from university, where we all got dressed up in Lilly for a colorful meal (I didn’t take the pinwheel with me haha, I was sending this to a friend to show her the colors of each print). This Chomp Chomp print dress and pinwheel were the first pieces of Lilly my husband bought for me when we were dating. I still have both, and I still love wearing this dress; the beadwork is amazing! The pinwheel isn’t very practical, so for now, it decorates my closet, adding a pop of color to it.

I wore this Spring Fever Toile print skirt the day after I graduated from U of M, as we were heading up, once again, to Grand Hotel on Mackinac Island. Each year, we go a few times, and I find its sprawling gardens and colorful rooms are the perfect complement to my Lilly outfits.

Another photo of Lilly Pulitzer I wore at Grand Hotel, this one is called the Miraflora Maxi Dress. We took this near their gorgeous fountain, near their garden, and tennis courts.

Another outfit I wore at Grand Hotel, this White Eyelet Sandrine dress, has long been one of my favorite Lilly pieces. With a pink J. Crew cardigan and pink glitter Kate Spade loafers, I felt feminine and put together while staying totally comfortable in Lilly!

There’s something about Lilly Pulitzer’s collection of pinks that screams summertime fun to me. I clearly can’t resist their gorgeous pink prints, but can you blame me?

Blue and white is a close second for my favorite color combination when it comes to Lilly Pulitzer clothing and life in general! I basically collect their blue and white prints. Whether it’s a dress, popover, or blouse, I can’t say no to this classic, timeless color combo.

I do visit other hotels aside from Grand Hotel, I promise! Haha. This one was at Hotel Walloon in Northern Michigan, and on a cool fall day, this cashmere Kassy cardigan kept me warm and cozy when I paired it with my Evangelia dress in this blue fish print. In Michigan, dress season is quite short, so to extend it, I wear lots of cardigans, blazers, and other layers, as you have probably noticed.

These are a few more looks I’ve worn around Michigan in the past few summers. Of course, I plan to wear more Lilly this spring and summer, so I’ll have to make a part 2 for this post. I also will start to wear everything in my closet at least once soon, so expect to see plenty of Lilly Pulitzer mixed in!