Skip to content

Ask Harry: Looking for the Right Sunglasses

The perfect sunglasses will give you an edge like none other, here’s how to find the best frames for your face.

By: Harry Rosen StaffDate: 2023-05-05

Shades, sunnies, glints, sun cheaters – whatever you want to call them, we can all agree there’s nothing better than finishing off an outfit with a pair of sunglasses that’s synonymous with you.

To find that perfect pair, there’s a few things to consider between things like face shape, temple width, and even colour. Let’s try on a couple to see what looks best for you.

Round Faces

A rounded face entails a similar width starting from the jawline to the brow, with fuller cheeks and soft curves. You’re going to want something with sharper angles to offset your sans-angular structure. Fortunately, you get to shop some of the hardest styles on the market – check out rectangular frames for more conventional looks, but don’t hesitate to get outside of the box a little with geometric shapes. Also, be particular about colour – if something like a glossy black is too much, go matte!

French Kiwis Oscar Square Sunglasses

French Kiwis

Oscar Square Sunglasses

$140
TOM FORD Redford Acetate Navigator Sunglasses

TOM FORD

Redford Acetate Navigator Sunglasses

$555
Gucci Shiny Havana Rectangle Sunglasses

Gucci

Shiny Havana Rectangle Sunglasses

$314.99$420Save 25%
TOM FORD Turner Pilot Sunglasses

TOM FORD

Turner Pilot Sunglasses

$660
Brunello Cucinelli Sartorial Sunset Acetate Sunglasses

Brunello Cucinelli

Sartorial Sunset Acetate Sunglasses

$1140
TOM FORD Ezra Rectangular Photocromatic Sunglasses

TOM FORD

Ezra Rectangular Photocromatic Sunglasses

$535
Gucci Shiny Acetate Full Rim Pilot Sunglasses

Gucci

Shiny Acetate Full Rim Pilot Sunglasses

$840

Square Faces

Just as Huey Lewis once said, it is in fact “hip to be square”. Social commentary on the pleasures of conformities and trends aside, the same balancing act of angles that applies to round faces applies to square faces – but in the inverse. The standout features of a square face being a broad jawline and forehead, look to break up that blocky structure with rounded edges – think aviator styles. It’s hard not to talk about these shades without channeling Frank Bullitt, Maverick, and Tony Montana charisma.

BOSS Ruthenium Pilot Sunglasses

BOSS

Ruthenium Pilot Sunglasses

$275
BOSS Metal Matte Aviator Sunglasses

BOSS

Metal Matte Aviator Sunglasses

$275
TOM FORD Dimitry Round Frame Sunglasses

TOM FORD

Dimitry Round Frame Sunglasses

$570
French Kiwis Romain Sunglasses

French Kiwis

Romain Sunglasses

$130
Gucci Rounded Frame Sunglasses

Gucci

Rounded Frame Sunglasses

$525

Rectangular Faces

Similar vibe to a square face, but a little longer. A rectangular face actually lends you a bit of headroom with how bold you want to go. Since this type of facial structure is typically larger, you can fully indulge in statement making oversized frames. We’re talking smoked out lenses, commanding shapes, and even funky colours if you’re going all in. From poker games to nights on the town, this is a big-time look.

TOM FORD Ilias Square Frame Sunglasses

TOM FORD

Ilias Square Frame Sunglasses

$645
BOSS Eco-Acetate Havana Shield Sunglasses

BOSS

Eco-Acetate Havana Shield Sunglasses

$305
TOM FORD Lorna Shield Frame Sunglasses

TOM FORD

Lorna Shield Frame Sunglasses

$615.99$770Save 20%
TOM FORD Redford Acetate Navigator Sunglasses

TOM FORD

Redford Acetate Navigator Sunglasses

$590

Heart-Shaped Faces

The heart face – wide forehead, narrow at the chin. The tapered nature of this face shape calls for glasses that will complement that facial transition, as onlookers are drawn onto your sculpted structure. Your best bet is a pair of smaller, rounded frames – sleek, compact, and inoffensive yet playful. It’s simply one of those frames that just work – go with anything from black and gold to light tortoiseshell finishes.

French Kiwis Jude Round Sunglasses

French Kiwis

Jude Round Sunglasses

$140
Brunello Cucinelli Sartorial Sunset Titanium Sunglasses

Brunello Cucinelli

Sartorial Sunset Titanium Sunglasses

$852.99$1138Save 25%
TOM FORD Raffa Round Frame Sunglasses

TOM FORD

Raffa Round Frame Sunglasses

$610
TOM FORD Raffa Round Frame Sunglasses

TOM FORD

Raffa Round Frame Sunglasses

$610
French Kiwis Jude Sunglasses

French Kiwis

Jude Sunglasses

$130
French Kiwis Nicolas Round Sunglasses

French Kiwis

Nicolas Round Sunglasses

$140

Oval Faces

Finally, the oval face. Legend has it that if you’ve got one of these, you can rock any pair of shades under the sun. From big and blocky, to subtle and understated, to bright and bold, play around and see what you like. But as always, fashion rules are just rules – learn them first, break them later.

TOM FORD Vincenzo Pilot Sunglasses

TOM FORD

Vincenzo Pilot Sunglasses

$670
French Kiwis Valentin Sunglasses

French Kiwis

Valentin Sunglasses

$140
Brunello Cucinelli Sartorial Sunset Acetate Sunglasses

Brunello Cucinelli

Sartorial Sunset Acetate Sunglasses

$1140
Gucci Acetate Rectangle Frame Sunglasses

Gucci

Acetate Rectangle Frame Sunglasses

$510
Zegna Navigator Frame Sunglasses

Zegna

Navigator Frame Sunglasses

$159.99$465Save 66%

Have a sartorial problem on your mind? Send us a message on Instagram @harryroseninc, and we’ll answer it here next time.

Read More From Our Ask Harry Series

TAGS:#Style Advice,#Ask Harry,#How To,#Accessories,#Eyewear,