Need Glasses? 3 Things Every Woman Should Consider

by Hillary Kerr

Have you ever had to deal with a friend going through an obsessive phase? You know: the type of insanity that’s often triggered by some sort of life event—like weddings—when all they can talk about is this single topic, usually with a laser-like focus that kind of freaks you out? True confession: For the past few months, I have been that friend, but not because I’m getting hitched. For me, trigger was something embarrassingly smaller, specifically: finding out that I needed my first pair of glasses.

I can hear what you’re thinking: Glasses! What’s the big deal? Get a grip, Kerr! Bear with me on this one. First of all, I’m a fighter pilot’s daughter, which means that along with inheriting my dad’s competitive nature and a moderate-to-serious wild streak, I also grew up enjoying better-than-average eyesight and stories about how my pops still had 20/10 vision well into his 40s. I just assumed I’d be the same, which is probably why it took me over a year of experiencing situational blurriness while reading late at night before I got my first eye exam as an adult.

I figured my doctor would tell me I had “Instagram eye”—which, like “phone thumb,” is a made-up condition I keep telling people is the new tennis elbow—and the prescription would be to stop staring at my phone so much. It turns out Dr. Kerr isn’t great at self-diagnosis, and even worse, my perfect vision is not exactly flawless. 

After an initial freak-out, I started to look at the bright side. What are glasses, after all, other than a fun new accessory? Even better: a necessary accessory! Cue the shopping montage!

But here’s thing: Even though I’m super skilled at buying myself sunglasses online, I realized I didn’t know a thing about selecting optical frames, or even where they were sold. In the hopes of figuring these things out, I decided to turn my personal quest into a story, and I enlisted the help of our amazing managing editor, Michelle Scanga, to round up all of the best frames on the market for our shoot. We wanted a range of styles, colors, and shapes, and today I’m delighted to share what I learned in the process.

Keep reading to see what I found out.

PHOTO:

Jenna Peffley

While I had a hunch about which styles of glasses would look best on my face—frames that are somewhat similar to my sunglasses—I figured it would be best to try a wide range of colors...

While I had a hunch about which styles of glasses would look best on my face—frames that are somewhat similar to my sunglasses—I figured it would be best to try a wide range of colors and shapes. First up: cat-eye frames! While I loved this style, the key (for me) was find frames that are large enough to fit my gigantic face; many styles were simply too small. That’s why it’s important to know the eyewear measurements you should be looking for, especially if you’re shopping online.

Slide the bar to see option two. 

Option 1: Cutler and Gross 0930 Glasses ($495) 53-17-145

Beloved British brand Cutler and Gross makes some of my favorite frames. They’re pricey, no doubt, but they’re very solidly made and feel luxurious and very well constructed. (Fun fact: Martin Scorsese’s go-to frames are C&G’s 0432 style.) I loved that this particular pair was on the strong side, thanks to the slightly thicker construction, but still felt ladylike.

Option 2: Steven Alan Optical Linden Glasses ($195) 53-15-140 in Dark Stripe Tortoise

Another option I really love is Steven Alan’s Linden glasses, which have a understated cat-eye shape and thinner, more feminine frame that is ideal for a subtler take on this style. They’re also super lightweight, so if that’s important to you, take note.

Next I tried something I never thought I’d like in a million years—round frames. Here’s the thing: In addition to having a big head and a big face, my face is also definitely...

Next I tried something I never thought I’d like in a million years—round frames. Here’s the thing: In addition to having a big head and a big face, my face is also definitely round. I figured that round glasses on my round face would be a big round disaster, but honestly, I was pleasantly surprised. It turns out that when I found frames that were the right proportions for my gargantuan cranium, I actually liked how they looked! (Imagine that…)

Slide the bar to see option two. 

Option 1: Garrett Leight Dillon Glasses ($285) 50-21-145 in Black/Size 50

Thin, round, and available in two sizes (47 and 50; the latter is shown here), this style was my gateway into this shape, because the frames have just the tiniest hint of cat eye to them. If you want to try high-contrast or a bold color, this style is a good one to start with, as the svelteness of the frame keeps it from overwhelming your face.

Option 2: Garrett Leight Milwood Glasses ($285) 49-22-145 in Dark Tortoise/Size 49

There are many great things about these Garrett Leight glasses, but my favorite is the fact that this frame is unisex. Like the Dillon glasses, it’s also available in two sizes (46 and 49), so you can choose the right size for your face. Obviously I went for the bigger pair.

One of the classic pieces of information I’d always heard about eyewear is that you should always opt for a pair that is the opposite of your face. So people with more square-shaped faces...

One of the classic pieces of information I’d always heard about eyewear is that you should always opt for a pair that is the opposite of your face. So people with more square-shaped faces should look for glasses with rounded lines to soften, while people with round faces (ME!) need rectangular or square frames to add contrast to their features.

Slide the bar to see option two. 

Option 1: Tom Ford Classic Soft Square Optical Frames ($475) 50-21-145 in Dark Havana

Like me, Mr. Ford is a Virgo who is obsessed with getting the details right, and it shows in these gorgeous glasses. Available in three colors, these are actually technically a men’s style, which reminds me: Everyone should look at all the styles a brand has to offer, not just the ones that correspond with their gender.

Option 2: Warby Parker Winston Frames ($95) 49-19-140 in Jet Black

My friend Will Kahn—who also happens to be the senior market and accessories editor at Town & Country—gave me lots of good advice about finding the right glasses, including the fact that Warby Parker should be at the top of my hit list. The prices are unquestionably right, and I adore the bold proportions and straight browline on this retro style.

In addition to finding the right frame shape, you have to consider the correct hue for your coloring. Since the majority of the glasses I tried on are black or tortoise, I figured trying some of...

In addition to finding the right frame shape, you have to consider the correct hue for your coloring. Since the majority of the glasses I tried on are black or tortoise, I figured trying some of the latest sheer or blond frames would also be worthwhile.

Slide the bar to see option two. 

Option 1: Oliver Peoples Ollie Glasses ($340) 49-18-140 in Buff

As a lover of all things ’50s, it’s probably no surprise I was super into this vintage-inspired style. While it comes in other colors, this iteration is really special, because it’s both strong in shape and super subtle in color. Between my blond hair, fair skin, and clear-ish frames, I essentially become the facial equivalent of a monochromatic outfit—and I like it.

Option 2: Oliver Peoples Executive II Glasses ($595) 47-21-140 in Matte Amber Tortoise/Brushed Silver

I was a bit nervous about trying a semi-rimless style because I was afraid that the combination of a colored brow bar (meaning the part at the top of the glasses) and a translucent lower half would leave my face imbalanced. I realized that, for me, all it took was finding a style that wasn’t so high-contrast, like the Executive II. The thin, blondish brown bar gives my face a little definition without knocking it off kilter, which is a good thing!

The final thing I considered was the finish—specifically, matte frames versus glossy styles. For reference, I pulled one of Cutler and Gross’s most beloved styles, the 0772, which has...

The final thing I considered was the finish—specifically, matte frames versus glossy styles. For reference, I pulled one of Cutler and Gross’s most beloved styles, the 0772, which has been in production for over 20 years.

Slide the bar to see option two. 

Option 1: Cutler and Gross 0772 Frames ($495) 50-21-145 in Blue on Black

Talk about statement glasses! These super-strong, ultra-glossy black glasses have just the faintest hint of blue along the center of the frames, which is subtle enough that you notice they’re not your average glasses but might not be sure why, at least on first glance. That element of surprise is delightful.

Option 2: Cutler and Gross 0772 Frames ($495) 50-21-145 in Matte Black

Whether it’s my hair or my lipstick, I tend to prefer things glossy, but I have to say, a matte frame feels really fresh. It’s a little subversive and unexpected, two qualities I would never normally associate with glasses. If you self-identify as an iconoclast or someone who likes to subvert the dominant paradigm, consider this finish.

Which style is your favorite? Let me know in the comments below! 

Photos: Jenna Peffley

Hair and Makeup: Noseph Trinh

Explore: Glasses

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