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Andrea Lavinthal, Style and Beauty Director: There are two things I just can't pull off style-wise no matter what any well-meaning Sunglass Hut sales associate or makeup artist says: Bold shades and bright lipstick. So I stayed firmly within my safety zone and paired a slightly oversize but still classic black style with a pale pink-nude gloss. Not the most daring duo, but it works for me.
Buy It! Warby Parker “Barrie” sunglasses, $95; warbyparker.com
Buy It! Nars Lipgloss in Turkish Delight, $26; narscosmetics.com
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Sharon Clott Kanter, Deputy Style Director: These frames pack a ton of attitude thanks to their rounded edges and mirrored lenses, so I decided to up the punchiness of the look with bright pink lipstick. But honestly the reason I'm obsessed with these shades has as much to do with the boldness of the style as the name of them — Hamilton — a soundtrack I've been listening to “non-stop” the last few weeks. I'm both helpless and satisfied!
Buy It! Illesteva “Hamilton” glasses, $290; barneys.com
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Alex Apatoff, Deputy Style Director: Because these clear frames are pretty statement-y on their own, I toned down my usual bold lip for an almost balm-like, barely-there (but buildable!) rosy shade that helps balance the mod vibe with something a little more feminine.
Buy It! Paul Smith “Eamont” sunglasses, $285; paulsmith.co.uk
Buy It! Glossier Generation G lipstick in “Crush,” $18; glossier.com
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Brittany Talarico, Senior Style Editor: According to the brand, these sunglasses are “inspired by lavish style and glamour of the supreme rulers of Ancient Egypt,” so I had to keep things glam with a bold pout. I love how the coral tone of the lip shade plays up the goldenrod mirrored lens. (TBH: I really picked the shades because they match my highlights.)
Buy It! Westward Leaning “Pharaoh 3” sunglasses, $245; westwardleaning.com
Buy It! Yves Saint Laurent Rouge Volupté Shine Lipstick in Corail Incandescent, $37; yslbeautyus.com
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Jackie Fields, Beauty Editor: Given these sunnies' retro pattern, I had to reach for a red lip. But I still feel like I’m living a modern day “Dolce Vita” thanks to the frame's updated shape (it’s not too square, yet not too round, and perfectly oversize), and the lipstick’s fashion-forward semi-matte finish.
Buy It! See “5556 Sun” sunglasses in Tokyo, $99; seeeyewear.com
Buy It! Givenchy Magnolia Couture Edition Le Rouge, $38; sephora.com
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Catherine Kast, Style Editor: I almost chose a red to go with these oversize retro-shaped shades, but I realized that this bold pink looked just as feminine with my overall look without being too try-hard, which can sometimes happen with a really defined red lip you're not someone who rocks that look every day. Also, my square face majorly benefits from this shape, and so do my light blue eyes: these glasses boast 100 percent UVA and UVB protection.
Buy It! Oliver Peoples “Abrie” Sunglasses, $365; saks.com
Buy It! Bobbi Brown Art Stick in “Electric Pink,” $28; bobbibrowncosmetics.com
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Sarah Ball, Fashion Market Editor: I always gravitate towards a bold cat-eye, but this pair felt a little edgier than I normally wear, so I thought I might as well go for it. For the lip I chose a bold pop of berry to play off the cool tones and extreme lines of the sunglasses.
Buy It! Aldo “Minser” sunglasses, $48; aldoshoes.com
Buy It! Bite “Bold Berry” lipstick, $26; sephora.com
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Lindy Segal, Style Social Editor: I like to (not-so-)humblebrag that my heart-shape face can wear pretty much any sunglass style, but I'll admit this is the first time I've done large round frames out of fear I'd look bug-eyed. But I ended up falling in love with the shape, and my bright pink lipstick was the perfect, summery complement to the light tortoise frames.
Buy It! Krewe du Optic “Louisa” sunglasses, $220; revolve.com
Buy It! Urban Decay lipstick in “Wonderland,” $17; sephora.com
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Jillian Ruffo, Associate Beauty Editor: These lenses are reflective, and reveal the most amazing magenta shade when turned at an angle – so off the bat, I was tempted to pair them with an equally bold lip color. But as someone who only wears nude lipsticks, I ultimately opted for a pastel pinky-lavender, which was still bright enough to pick up the color in the glasses while fitting my muted-lipstick needs.
Buy It! Dior Square Abstract Havana Sunglasses in Purple, $490; neimanmarcus.com
Buy It! Burt's Bees Lipstick in Tulip Tide, $9; macys.com
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Kaitlyn Frey, Style Intern: I'm normally all about cat-eye shades, but I decided to step out of my comfort zone with these oversized gold aviators. I paired them with my classic, go-to nude lip I love for the summer.
Buy It! Oscar de la Renta Swarovski Crystal Metal-Acetate Aviator Sunglasses, $360; oscardelarenta.com
Buy It! Dolce & Gabbana 'Dolce Nudo,' $37; nordstrom.com
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Emily Kirkpatrick, Associate Style News Editor: My usual pair of sunnies are a pair of large, black Ray-Ban-esque shades that cover minimum 50 percent of my face – but for this project I decided to switch it up, opting for a style that's completely new to me, a circle frame fittingly named “Geek Chic.” Luckily, the majority of my face was still totally covered so I felt right at home. As for the lipstick, I just dyed my hair pink (stay tuned for the full story) so I'm still a little confused about exactly what colors work best with my new do. I went with a tried and true favorite, this red-orange lipstick from MAC that really makes my eyes pop … not that you can see them behind all that shade I'm throwing.
Buy It! Perverse Geek Chic Round Sunglasses, $45; perversesunglasses.com
Buy It! Mac Cosmetics So Chaud Lipstick, $17; bloomingdales.com
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Karen Werling, Designer: The thing I love about these Gentle Monster shades is that they look totally different depending on the angle you see them from since they're majorly mirrored: This pair is actually entirely silver! Because they're so modern and out there, I picked a simple, sheer tinted balm. A funky neon matte would look cool if you're channeling your inner Rihanna, but for every day, this is my jam.
Buy It! Gentle Monster “Love Punch” in Silver. $290; en.gentlemonster.com
Guerlain KissKiss Roselip in Crazy Bouquet; sephora.com