Apparently “preppy” means something different to gen-z than it did to us millennials and younger, so note that I’m using the antiquated definition here (ha), but I have been loving the reprise of classic preppy pieces and styles this season. I don’t really think this look ever “goes out” — I see elements of it all the time everywhere I look — but there has been a particular focus on it this season, especially with the much-hyped boat shoe! (I ended up ordering this Scarosso pair in the dusty pink, seen above, but have these very popular Madewell ones on my radar for this fall. Love the rope cord laces.)
Below, sharing some iconic pieces that feel new again to me —
BOXER SHORTS // BLAZER // PEARL NECKLACE // BOAT SHOES // BARBOUR JACKET // BALL CAP // WATCH // LV NEVERFULL TOTE
And there are so many ways to reinvent the look. Just take a gander at this “undone prep” look I found on Pinterest. The components are classic but the styling, slouch, and unexpected boxer-style short make them new again.
Below, some other favorite preppy pieces to contemplate incorporating into your wardrobe this fall:
01. A sailboat motif sweater always feels right at home in this aesthetic. I like the idea of pairing this with some bandana-print shorts (or boxer-style shorts).
02. Per my note above, on my fall wishlist: these boat shoes.
03. A classic denim button down. I own and love this.
04. Iconic ball cap.
05. An LV Neverfull! The more lived-in the better.
06. My forever go-to: the LL Bean Boat and Tote. This is my favorite gift to give when I don’t know what to give. Perfect for a bride-to-be with her new monogram, a new mom, a college grad, a neighbor!
07. These watches look heirloom but cost much less than you’d think. I own the black one.
08. When I think of fall preppiness, I immediately think of the classic Barbour jacket.
09. A good cable knit. Love the idea of this with an undone pant — boxer style short, barrel-fit jeans, etc.
10. Speaking of: barrel legs!
11. I had to have this madras dress when I saw it! So nostalgic for me. The number of madras pants and skirts I had from A&F…!
12. A double breasted blazer — my personal favorite from VB. You will wear this from now until eternity. Looks so chic with dark wash denim and a white tee.
14. If I could only ever wear one sweatshirt, it would be something like this.
15. Had to include a strand of pearls! These are a great price.
16. East Coast energy.
17. An all time favorite pair of sunglasses. Classic for a reason.
18. I love how the boxer short trend fits right into the preppy vibe.
19. Lacoste polos.
Ways to Style The Prep Aesthetic.
BARBOUR JACKET // SUEDE BOAT SHOES // LV TOTE // BARREL LEG PANTS // CABLE KNIT // WATCH
SWEATSHIRT // BUCKET BAG // SNEAKERS // LOUNGE PANTS // PEARL EARRINGS // PEARL NECKLACE
BUCKET BAG // RL DENIM BUTTON DOWN // BARREL LEG PANTS // SNEAKERS // HERMES SCARF // DORSEY NECKLACE
P.S. Surprise is our original factory setting.
P.P.S. Amazon back to school finds.
P.P.P.S. Work ready dresses.
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I had to chuckle at the heading of this post…I’m not sure you ever left your preppy roots and I mean that in a ‘bless her’ southern way.
LOL. Guilty as charged.