DAY AT THE BEACH
Going to the beach on a first date can be overwhelming to say the least. Impress him with your confidence—and there is nothing that screams confidence like showing you’re comfortable in a bathing suit. Whether you opt for a bikini or a chic one-piece, go for something colorful and with a print that shows off your fun side.
Marysia Swim Broadway Bikini, $272; marysiaswim.com
Illesteva Hamilton D-Frame Acetate Mirrored Sunglasses, $290; net-a-porter.com
Cuyana Canvas Beach Tote, $110; cuyana.com
Melissa Odabash Macrame Shorts, $200; stylebop.com
Steve Madden Malta Sandals, $70; stevemadden.com
OVERLY AIR CONDITIONED MOVIE THEATER
Being too cold on a date can make it difficult to focus on the task at hand: the date! Make sure you dress for where you’re going. In the case of a movie date, you can never be too prepared for heavy air conditioning. Wear a long-sleeve dress or bring a sweater and a patterned scarf so you’re comfortable and don’t feel schlumpy. In case of emergency, ask for your date’s shirt. Win, win.
Jennifer Fisher Large Single Ball Cuff, $650; jenniferfisher.com
Alexa Chung for AG Jeans Pixie Denim Mini Shirt Dress, $325; net-a-porter.com
Gucci GG Blooms Print Silk Scarf, $440; gucci.com
Tory Burch Shoulder Bag, $475; bloomingdales.com
Zara Leather Studded Clogs, $100; zara.com
OUTDOOR DAY CONCERT
Concert dates are all about accessories. Chokers, fringe bags, gladiator sandals, and, of course, a round pair of sunnies are must-haves for the occasion. Instead of the standard denim shorts and T-shirt, find a playful patterned romper that lets you show off your moves.
Boohoo Savannah Capped Sleeve Daisy Print Playsuit, $20; boohoo.com
Ray-Ban Round Fleck Sunglasses, $175; stylebop.com
Topshop Mini Suede Fringe Bag, $58; topshop.com
Aldo Leola Sandal, $120; aldo.com
Wendy Nichol Textured Leather and 14-Karat Rose Gold Choker, $1,245; net-a-porter.com
SWEATY BAR
Non-air-conditioned bars are not ideal settings for looking your best. You get sweaty and sticky and that is not chic. Body suits, while not ideal in a bathroom, provide an easy outfit solution. And they’re super sexy.
Boohoo Caitlyn Strappy Front Plunge Sleeveless Bodysuit, $20; boohoo.com
H&M Cuff Bracelet, $6; hm.com
Abercrombie & Fitch One Teaspoon Outlaws Shorts, $118; abercrombie.com
Tamara Mellon Elixir Embellished Elaphe and Suede Bucket Bag, $1,295; net-a-porter.com
Tabitha Simmons Leticia Perforated-Leather Sandals, $695; modaoperandi.com
FANCY-SHMANCY DINNER
A fancy dinner is not a go-to first date, but if the moment presents itself, seize it in a fiery red dress that doesn’t show too much skin. This is your moment to be elegant!
3.1 Phillip Lim Ruffled Silk-Crepe Dress, $695; net-a-porter.com
Anita Ko Rose Flower Studs, $1,995; anitako.com
Kotur Levin Jackpot Perspex Box Clutch, $795; net-a-porter.com
Topshop Ruby Metallic High Sandals, $22; topshop.com