WhoWhatWear

Ray-Ban Aviator Large 55 Sunglasses ($183)

When working with wide cheekbones and a narrow chin, otherwise known as a heart-shaped face, aviators are your best bet. That said, Montoya suggests staying away from oversized aviators with lenses that slope sharply from the nose pad to the outer cheekbone; this shape can weigh or drag the face down. Instead, pick ones that have a more rounded silhouette throughout. Additionally, cat-eye sunglasses that are not too narrow or pointy will also work for this shape.

Topshop Aviator Sunglasses

Oliver Peoples Annaliesse Sunglasses ($365)

Prism Portofino Eye Matte-Acetate Sunglasses ($425)

Lucky for oval faces, Montoya says that just about every frame type complements this shape. "Just make sure that when choosing sunglasses--whether oversized or not--you pay attention to the width of the frames and the distance between the two lenses," he says. "There should be a gap on either side of your temples, and the sunglasses should not slide down the nose or cause discomfort in the nasal area." The color of the frame is important as well, Montoya points out, and in this case, you'll want to stick to colors that look best on you clothing-wise and translate that to sunglasses.

Anthropologie Sliced Geometry Shades ($38)

Karen Walker Wizard Sunglasses ($275)

Illesteva Frieda Round-Frame Matte-Steel Sunglasses ($285)

Square faces with a small forehead and strong jaw line should pick circular frames for a balanced look. You should avoid square styles or frames with hard shapes. "I recommend choosing sunglasses with softer, more rounded edges or even an oversized cat-eye, as those will complement broad features," says Montoya.

Giuse by Benjamin Eyewear Milton Sunglasses ($175) in Black

Madewell Sunglasses ($55) in Beach Pebble

Stella McCartney Oversized Square Sunglasses ($353)

Forever 21 Square Sunglasses ($6)

Benjamin Eyewear Brotherton Sunglasses ($375) in Tortoise