The Preppy Revival
Boat shoes are back, Must have button downs, White denim I swear by, and What I'm Wearing to the Tennis Tournament and the Masters
Let’s talk shoes. Glorious, fabulous, personality-defining shoes.
I’ve always had a thing for them. My earliest memory? Perched on one of those tall, wooden thrones at Stride Rite, getting my tiny feet measured like royalty for a pair of canvas kicks. That was my gateway shoe.
Then came The Dingo Boots Incident. Picture this: Jacobsons. A Fancy department store. My even fancier grandmother. A single pair of Dingo boots in my size-ish (read: a full size too small). But I wanted them so badly that I pulled the ultimate kid con and claimed they fit. They didn’t. I limped proudly for weeks. Nothing was going to come between me and those boots!
And who could forget the Punky Brewster high tops? These weren’t just sneakers they were a mission. Pre-internet, pre-next-day-delivery, pre-anything-easy, my mom and I had to drive 40 minutes to another mall because a saleslady tracked down a pair in my size. Worth it? Obviously. Street legal in gym class? Absolutely not. Did I rock them anyway? Like a tiny fashion anarchist.
Then came the Sam & Libby ballet flat era. A special day indeed. I, of course, chose hot pink. Why? Because they go with everything, obviously. (Still true. Don’t argue.)
Looking back, maybe it was the school uniform that sparked my love for shoes. Shoes were the only way we could express any form of style or personality. You could not pick your shirt or your skirt but your shoes? Your shoes were everything! And for me and everyone else on the prep school circuit, boat shoes were the holy grail. We wore Sperrys, Docksiders and Eastlands. Every year a new pair for back to school. That soft leather. Those rawhide laces. That rubber sole that somehow made us feel nautical, even if we never had set foot on a boat.
Which brings me to this breaking news:
BOAT SHOES ARE BACK, BABY!!!
Honestly, did they ever really leave? My husband doesn’t think so as he’s kept two pairs on deck at all times. One polished and ready for pubic viewing, the other beat up and perfect for rainy days or grocery store runs. But I’m telling you all now—order your pair while you still can. Designers are already rolling out their reimagined versions (some of which are giving me anxiety with their price tags). Miu miu has already done them. And so has Loewe. There are slim versions for women and this iconic brand did a collab with chic colorful laces. For me? I’m sticking with the classics. Give me that crisp, preppy energy that screams classic and timeless. That screams prep school kid. The nostalgia of boat shoes really takes me back but it’s a trend I’m excited is coming back around. This is the pair that I am getting for our trip to the Cape!
Thank you for taking this stroll down memory lane with me because shoes are never just shoes. They’re time capsules. Personality statements. Emotional support with laces. And sometimes, they’re just hot pink flats that go with everything.
Not into boat shoes? I shared all my favorite Spring shoes here.
A Crisp Collar
I’m not reinventing the wheel here, but I am giving it a very crisp collar. I have been living in a button down and jeans lately. It’s classic and easy. It looks like effort, but it’s secretly just…not!
I recently discovered Untuckit makes women’s shirts and honestly they are a game changer. NO wrinkles and NO gaping buttons. Just a great fit and actual structure. I picked up a white one, a pink one and a striped one. I also grabbed one of their shirt dresses because it gives me “South of France” energy even if I’m just running to the store in Charleston.
White Denim Done Right
Hot take: I wear white jeans more than blue ones from March through August. As someone who clocks in at five foot two, I swear by cropped bootcut styles. They’re flattering, timeless and they work with everything from sneakers to sandals. I keep two pairs in rotation. One with a raw hem and one with a clean finish.
TIPS: Often times I size up in white denim. I like it to skim not squeeze as white denim is less forgiving than blue. I also frequently have my front pockets sewn closed so you cannot see the pocket line. My top 10 pairs are linked here.
Tennis Core
Charleston’s Credit One Open is this week and I am attending the tournament one day and I have a viewing party on the last day of the tournament. I have two great looks planned.
Courtside look: this dress or this dress, retro sneakers, hat
Viewing party look: crisp white shirt dress, gold earrings, sandals and a tote
Comfortable enough to watch the match. Cute enough to be photographed next to a bottle of champagne.
The Masters
Golf core is tennis core’s relaxed cousin. The one who prefers a chilled glass of sauvignon blanc over a protein shake. For our Masters viewing party, I’m thinking:
Polished tailored skort and a collared top OR this skirt and top
Or this dress with a little nod to Agusta green OR this dress
These looks are sporty and chic and deserve a spot on your Instagram page.
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'Tiny fashion anarchist' is my fave new phrase