5 Great First Date Looks for Women Over 50

Entering the dating pool after the midcentury mark can be daunting. Whether you are divorced, have never been married or are widowed, it’s a fine line between wanting companionship and intimacy — and putting yourself out there. Best to test the waters a bit before making a big splash.

I’m married, but I have plenty of friends trying to navigate this course. Whether you visit online dating sites, are being set up on blind dates by well-meaning friends or you were lucky enough to meet someone interesting on your own, a first date can raise the question of what to wear. Your clothing choices can telegraph a lot about who you are and your confidence. Obviously, where you are meeting and what you are doing are factors too.

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If you are meeting for a coffee and want to keep it casual:​

Gap 24/7 Split-Hem Cable-Knit Sweater ($63, gap.com)

Gap

Neutral colors, relaxed shapes and inviting textures (cashmere, suede, denim) give off an easygoing vibe. Pair a sweater like the Gap 24/7 Split-Hem Cable-Knit Sweater ($63, gap.com) with some casual jeans like Levi’s 501 Original Fit Women’s Jeans in Erin Can’t Wait Medium Wash ($76, levi.com/US/en_US/) and boots like Cologne Arlo 2 Dark Sand Suede Boot ($45, clarks.com) ​and then top with a cozy jacket like the Quebec Sherpa in Antique White ($98, marinelayer.com)​. Potential add-ons: A leather shoulder bag or cashmere scarf.

If you are meeting for dinner and want to look elegant:

Clockwise from left: Travelers Classic Dress in Black ($99, chicos.com); Tailored Wool Coat in Medium Brown ($120, shop.mango.com); AllSaints Double Chain Link Bracelet in Gold Tone ($69, bloomingdales.com); Sam Edelman Women’s Vienna Mid-Heel Pumps in Black ($140, macys.com)

Photo Collage: AARP; (Source: Mango; Chicos; Nordstrom; Macy’s)

Assuming that you will be going to a proper restaurant, you can’t go wrong with a little black dress like the Travelers Classic Dress in Black ($99, chicos.com) and pointy-toed, low-heeled pumps like Sam Edelman Women’s Vienna Mid-Heel Pumps in Black ($140, macys.com). A tailored coat in classic camel like the Tailored Wool Coat in Medium Brown ($120, shop.mango.com) and a gold chain-link bracelet like the Panacea Link Stretch Bracelet ($30, nordstrom.com) convey that all-elusive air of quiet luxury. Potential add-ons: Small drop or stud earrings, or a leopard-print scarf.

If you are meeting to play pickleball and want to seem energetic and fun:​

Left to right: Embroidered Pickle Ball Bag Canvas With Monogram in Navy with Lime Stitching ($69, pitchastitch.com); Ace Tennis Skort 15.5” in Bright White ($69, athleta.gap.com)

Photo Collage: AARP; (Source: Pitch A Stitch Plus; Athleta)

​A vividly patterned polo like the Lilly Pulitzer UPF 50+ Luxletic Frida Polo in Deeper Coconut Ride With Me ($128, lillypulitzer.com) with built-in SPF and a flirty but not-too-short tennis skort like the Athleta Ace Tennis Skort 15.5” in Bright White ($69, athleta.gap.com) will get the ball bouncing. A supportive, chic athletic shoe like the NikeCourt Air Zoom Vapor Pro 2 in White/Lime ($130, nike.com) and a cute, monogrammed pickleball bag in complementary colors like the Embroidered Pickle Ball Bag Canvas With Monogram in Navy with Lime Stitching ($69, pitchastitch.com) definitely hit the mark. Potential add-ons: Cool shades and a baseball cap or visor.