With this year’s buzz around Carolyn Bessette Kennedy and her signature Selima Optic sunglasses everywhere, I’m forever thinking about the pieces that never really go out of style. This got me wondering, if you only had one item per category in your wardrobe, what would you choose?
My mind immediately goes to Jane Birkin and her Birkin – those pieces we reach for again and again that become part of our personal style. Other items that come to mind are Manolo Blahnik’s Calamu 50 mules (or options like Stuart Weitzman’s minimalist Slide 50 sandals and Ayde’s black Vero sandals), Ferragamo pumps, Cartier Tank Louis watches, and classic Prada and Chanel bags. I also think about brands like The Row, Khaite, Totem, Rue Sophie and Saint Agni.
I asked our editors to share what they consider truly timeless. Judith Jones and Anna LaPlaca both noted Ray-Ban’s Wayfarer styles that stand the test of time. Below, see all the accessories they swear by.
(Image credit: Judith Jones)
ray ben
Mega Wayfarer Polarized Square Sunglasses
“It seems like I’ve collected a lot of sunglasses, but I always come back to my Ray-Ban Mega Wayfarers. They’re classic, versatile and cute and look great with every outfit.”
“I wear ballet flats year-round here in LA, and it doesn’t get any more timeless and comfortable than Margaux’s demi flats. They’re the kind of flats you’ll get on repeat.”
B-Take The Belt
adrian leather belt
“A beautiful and classic black belt that always pulls my look together instantly.”
(Image credit: Erin Fitzpatrick)
strathberry
Mosaic Leather Top Handle Bag
“Strathberry bags have all the hallmarks of quadruple-figure designer editions – impeccable craftsmanship, high-quality leather – without the excessive markups. They’re handmade in Spain and are super timeless. It’s my everyday bag for work, shopping, brunching, etc.”
Calvin Klein
classic butterfly sunglasses
“I’m not very adventurous when it comes to sunglasses. I don’t really try out all the funky colors and shapes on the market. These Calvin Klein ones are simple and chic – right up my alley.”
But
CloudPulse 2 Training Shoe
“You’ll never be able to take my On shoes off my feet. They’re incredibly comfortable and classic. If you want to go the anti-trend route, wear white.”
(Image credit: Alison Pair)
GHBASS
Whitney Weijns Penny Loafer
“When I think of timeless shoes the first thing that comes to mind are Penny loafers. The second thing that comes to mind are the GHBass Whitney Weejuns. They are exactly what I look for in a pair of loafers: simple and polished.”
oliver peoples x khayte
1983C Cat-Eye Acetate and Gold-Tone Sunglasses
“I’ve seen these Khaite
Quarrel
90s short textured leather tote
“I’m so obsessed with The Row’s ’90s bag that I have it in three colors. It’s the perfect little bag for every occasion – day and night. It’s so simple and low-key that I don’t think it will ever be considered dated, and it’s a hallmark of The Row bags as a whole.”
(Image credit: Anna LaPlaca)
ray ben
Classic Wayfarer Polarized Sunglasses
“There’s something about classic Wayfarers that looks good on everyone who wears them, and I can’t believe I waited so long to buy a pair. All the other sunglasses don’t have to.”
“I have over 15 belts, but this is still the one I reach for the most. It makes every outfit look 50% more put together.”
Loro Piana
calf leather ballerina flat
“I’ve loved Loro Piana Rebecca flats for years, and for me, they are the ultimate investment shoe. Sure, they’re technically flats, but elegant enough to rival my heels.”
“I’ve been on a shopping hiatus for six months, but this is the next purchase I plan on making. I know I’ll wear these every day, even with a white T-shirt.”
(Image credit: Audrey Hiayaui)
“My dream investment are ballet flats – I feel like nothing could be more timeless than these.”
“Ferragamo Vara Soft Pumps are so chic and classic.”
prada
Pre-Owned 2013-2026 Medium Spazzolatto Galleria Double Zip Satchel
(Image credit: Josephine Hadjiloukas)
prada
Passage Medium Leather Bag with Re-Nylon Flap
“I think the Prada Passage Bag is a worthy candidate for a modern accessory that feels timeless.”
“If I won the lottery, I would keep it a secret, but there would be hints.”
Miu Miu
Miu Regard Sunglasses
“I wear glasses and need a new style. Put this at the top of my wish list.”
alex mill
Selima Caroline Sunglasses
“Speaking of CBK, take a look at these frames.”
Shop More Timeless Accessories
cartier
tank louis cartier watch
Celine
triumph oval sunglasses
These iconic Celine sunglasses.
I have to include these vagabonds from The Row.
Hermes
Pre-Owned Kelly Handbag Black Box Calf with Gold Hardware 32
Hermès bags feel like a blueprint for timeless accessories.
The perfect Chanel sunglasses.
Chanel bags never go out of style.
Ayde
black vero leather mules
oliver goldsmith
manhattan
As seen on Audrey Hepburn breakfast at Tiffany’s.
st agni
90s belted shoulder bag
carrel
Carlotta Black Leather Ballet Flats
Shoes from the beloved French brand Carrel.
