A guide to sunglasses by frame shape, from cat eyes and butterflies to ovals, rounds, squares and aviators. It covers how the shapes came about and how to try a pair on properly.
Sunglasses That Change the Whole Face: Cat Eyes, Ovals, Rounds and Aviators

In 1929 Sam Foster sold his first pair of sunglasses on the Atlantic City boardwalk, and Vogue notes it was the start of mass production. Yankee Magazine adds the part I love: he pitched them as a fashion item, not only as eye protection. Nearly a century later that is still how I think about sunglasses. They are the one accessory that changes your whole face in a second, and the shape you pick decides the mood.
My honest point of view is that the shape comes first and the brand comes second. Start with the cat eye, which has a nice origin story. The Dana Hall School archives say Altina Schinasi designed the Harlequin glasses, also known as cat-eye glasses, taking inspiration from harlequin masks. She received the Lord & Taylor American Design Award in 1939, and Vogue and Life magazine recognized her frames. That sharp upward flick is still doing the same job.
The first group is built around it. The CELINE Triomphe Cat Eye, 55mm is the clean, confident one, and it shows up twice here, which tells you something. The Bottega Veneta Black Icons Cat Eye in black and the Sardine cat-eye in brown are the two I would compare side by side: black is graphic, brown is softer against skin. The Saint Laurent Cat Eye, 57mm and the Gucci Light Cat Eye, 58mm and Minimal Cat Eye, 54mm are the wearable middle, sharp enough to notice and quiet enough for a trench and jeans.
Then the more playful pairs. The Bvlgari Serpenti Forever in brown has a little jewelry detail at the temple. The Loewe Coil cat-eye in black is bolder, and the Alaïa Logo Lettering cat-eye in brown puts the name right on the frame. The Le Specs Le Bijou, 55mm is the lighter, friendlier option, and the Swarovski Butterfly, SK6049 is the one to wear with a slip dress when you want a little drama.

Cat eye and butterfly sunglasses

Triomphe Cat Eye Sunglasses, 55mm
CELINE

Black Icons Cat Eye Sunglasses
Bottega Veneta

Sardine cat-eye sunglasses
Bottega Veneta

Serpenti Forever cat-eye sunglasses
Bvlgari

Le Bijou Cat Eye Sunglasses, 55mm
Le Specs

Coil cat-eye sunglasses
Loewe

Cat Eye Sunglasses, 57mm
Saint Laurent

Butterfly Sunglasses, SK6049
Swarovski

Light Cat Eye Sunglasses, 58mm
Gucci

Logo Lettering cat-eye sunglasses
Alaïa

Triomphe Cat Eye Sunglasses, 55mm
CELINE

Minimal Cat Eye Sunglasses, 54mm
Gucci
Ovals and rounds that go with everything
Ovals and rounds are the easy ones. The optometrists.org frame guide says oval faces are the most universal face shape, and that square faces are generally balanced by a round or oval frame, so these curves are a safe place to start if you are unsure. I find they also soften a sharp blazer or a stiff white shirt.
The oval pairs here are the ones I would reach for most. The Miu Miu Regard Oval, 50mm and the Miu Miu Oval, 52mm are small and neat, and I would wear them with a slicked-back bun and a knit. The Coach Oval, 53mm and Coach Oval, 54mm are the relaxed, everyday pair, and they have the right size for a quick errand. The Saint Laurent Oval, 54mm is a little more serious. The DIOR DiorOblique B1I Oval, 52mm carries the house pattern, which is a nice detail for a plain outfit. The Bvlgari Serpenti Viper oval in black is the sleek one, with the same snake motif as the cat eye.
For rounds, the Celine Eyewear Circle Défilé in black is my favorite shape of the group, a full circle that looks great with a cropped jacket. The Loewe Coil round in silver is the cool one, great against a gray coat. The two Valentino Garavani L'8 VLogo rounds, one in brown and one in black, are the pair for a soft dress and loafers, and brown is easier with warm tones. The PRADA Symbole Round is the minimalist, with that tidy emblem, and it is the pair I would hand to someone who wants a round frame without fuss.
A small test: look straight into a mirror and check that the frame does not sit on your cheeks when you smile. If it does, try the next size down.
Oval and round sunglasses

Oval Sunglasses, 53mm
Coach

Regard Oval Sunglasses, 50mm
Miu Miu

Circle Défilé round sunglasses
Celine Eyewear

Coil round sunglasses
Loewe

Oval Sunglasses, 52mm
Miu Miu

Oval Sunglasses, 54mm
Saint Laurent

L'8 VLogo round sunglasses
Valentino Garavani

L'8 VLogo round sunglasses
Valentino Garavani

Symbole Round Women's Sunglasses, PR 19ZS
PRADA

Oval Sunglasses, 54mm
Coach

Serpenti Viper oval sunglasses
Bvlgari

DiorOblique B1I Oval Sunglasses, 52mm
DIOR
Squares, rectangles and aviators with an edge
Squares and rectangles are for days when you want an edge. The aviator is the one with the longest history. The BBC reports that the first Ray-Ban aviators, with green lenses that cut glare, reached the public in 1937 with a plastic frame, and that the style came out of a 1930s effort by Ray-Ban's parent company to protect US pilots' eyes from glare. It still looks great with a white tee and a leather jacket.
The Ray-Ban Brow Bar Aviator, 59mm is the classic pilot shape with a bar across the top that adds some attitude. The Le Specs Le Mimi Aviator, 57mm is a lighter, more feminine take, and the OTRA Stevie Aviator, 58mm is the one I would pick for a sharp suit. They are bigger than the round pairs, and that is the point.
The squares are more architectural. The DIOR DiorMidnight S1I Square, 53mm is strong and sleek, and the FERRAGAMO Square, 54mm is a little calmer. The Dolce&Gabbana Square, DG4513 is the one I would wear with a simple dress and a red lip. The PRADA Rectangle, PR D01S is slim and modern, and it looks like part of a tailored look. Then there is the Phoebe Philo Sliced Cruise rectangular frame in yellow, which is the one to wear when everything else you have on is black or beige.
What I would skip: a sharp square frame with a sharp blazer and a sharp haircut, because everything ends up fighting. Soften one thing, either the frame or the outfit. I would also skip buying a pair that you only tried on once in bright store light, and any frame whose arms press behind your ears.
Square, rectangle and aviator sunglasses

Stevie Aviator Sunglasses, 58mm
OTRA

Sliced Cruise rectangular sunglasses
Phoebe Philo

DiorMidnight S1I Square Sunglasses 53mm
DIOR

Square Sunglasses, 54mm
FERRAGAMO

Rectangle Sunglasses, PR D01S
PRADA

Brow Bar Aviator Sunglasses, 59mm
Ray-Ban

Le Mimi Aviator Sunglasses, 57mm
Le Specs

Square Sunglasses, DG4513
Dolce&Gabbana
How I try on a pair and what to check
Here is how I try on a pair. I stand at a window, not under a store lamp. I check that the frame covers or sits near my brows, because an optometrist quoted by Reviewed says it simply: the bigger the better. Then I shake my head and smile, and see whether they slip.
For eye care, I stay general. The American Academy of Ophthalmology says to look for a tag promising 100% UV protection, or UV400, and that a label reading UV absorption up to 400nm is also acceptable. It also says oversized or wraparound frames help cut down on UV entering from the side. Read the label on the pair in your hand, since it is the label that counts, and remember that polarization reduces glare but does not itself provide UV protection.
Jackie Kennedy Onassis kept several pairs in a basket by her front door, according to TIME, and I think that is the best habit to borrow. Keep a pair where you will see them on the way out.






