12 Gilt Girls Share Their Go-To Date Looks


If you’re about to embark on a new romance, that first impression means everything, so what do you wear? Inspired by tomorrow’s Perfect Outfit: First-Date Style sale, we asked the lovely ladies in our office to share their must-haves for building a standout, head-to-toe look for a much-anticipated rendezvous. Check out their tips and don’t be afraid to steal a few ideas for yourself!

Chassie: “I prefer to go bold, as subtlety is lost on me — a fitted, patterned dress, a cropped and studded leather jacket with some real shoulder action, and brightly colored booties.”

Megan: “My go-to date night outfit is a great-fitting pair of black skinny jeans (because — lets face it — black is just more flattering) paired with a structured blazer, and a pointed toe pump to give me the extra lift my 5’2 frame needs. It’s comfy, cute and a little sassy! And I always bring my favorite accessory to hold the essentials — a killer clutch.”

Shayna: “I love a flowing button-down in a vibrant print, my best-fitting skinny jeans, and sky-high wedges. It’s fun, and I’ll definitely be prepared for any spontaneous after-dinner activities!” 

Katherine: “I think a perfect first-date outfit is one where you look and feel great, without trying too hard. You want the focus on you, and for me, that outfit usually involves a soft, loose T-shirt, skinny jeans, and single-sole pumps. I like to finish off the look with simple jewelry (like studs or a dainty necklace), natural make-up, and a cool-girl leather jacket.”

Jane: “I’m all for throwing on my perfect white tee or a silk button-down with black leather pants. And I top it off with some fun heels and an oversized clutch.”

Meredith: “I always turn to my staple — my favorite black suede booties — and I usually wear a mini skirt, a classic tank, and a leather bomber jacket. Every date night outfit needs accessories, so I usually wear a gold cocktail ring, my nameplate necklace (I’ve had since the 4th grade), and a black handbag.”

Alyse: “For a nice, warm-weather date night, I would thrown on a breezy sweater, a lace skirt, and spring booties. I’d also carry a small clutch or a white shoulder bag.”

Lauren: “On a first date, I like to go with a simple, silk blouse, a high-waisted skirt, wedges, lots of bangles, and a leather jacket to bring an edge to an otherwise very feminine look.”

Marissa: “For date night, my go-to is definitely leather pants and a bright silk tank! Carrying a cool clutch and accenting with bangles and great earrings is a must!”

Shana: “I love to feel both comfortable and fashionable on date nights. A pair of leather shorts paired with a silk blouse and comfortable platform heals are my go-tos. I also always ensure my nails are painted and I’m in a great shade of lipstick.”

Aileen: “I always reach for leggings, a silk button-down, and high-heel booties. And depending on the (unpredictable) NYC weather we’ve been having, I might bring along a leather jacket too!”

Tiffany: “I’m usually running from work to dinner, so my date-night outfit is pretty simple: my favorite white shift dress, vintage gold earrings, strappy sandals, and a small leather purse I can pull out of my work tote.”


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