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5 Great First Date Looks for Women Over 50

Let your outfit show your interest level and hint at your personality

Cindy Weber-Cleary,

AARP

En español

Published February 22, 2024

Tailored Wool Coat in Medium Brown; Travelers Classic Dress in Black; Sam Edelman Women’s Vienna Mid-Heel Pumps in Black; AllSaints Double Chain Link Bracelet in Gold Tone

Photo Collage: AARP; (Source: Mango; Chicos; Nordstrom; Macy’s; Getty Images (3))

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:

Travelers Classic Dress in Black; Tailored Wool Coat in Medium Brown; AllSaints Double Chain Link Bracelet in Gold Tone; Sam Edelman Women’s Vienna Mid-Heel Pumps in Black

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:

Embroidered Pickle Ball Bag Canvas With Monogram in Navy with Lime Stitching; Ace Tennis Skort 15.5” in Bright White

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.

If you are meeting at an exhibition or lecture and want to be taken seriously:

The Sofia Straight Pant in Winter White; Bixby Readers in Hemognar; Zoe Ballet Flats in Leather in Black

Clockwise from left: The Sofia Straight Pant in Winter White ($109, anntaylor.com); Bixby Readers in Hemognar ($110, caddislife.com); Zoe Ballet Flats in Leather in Black ($70, jcrew.com)

Photo Collage: AARP; (Source: Ann Taylor; Caddis; J. Crew)

Quiet meeting places call for a muted color palette. A black shirt with white collar and cuffs in a surprise fabric (georgette!) like the Lauren Classic Fit Two-Tone Georgette Shirt in Black/Mascarpone Cream ($145, ralphlauren.com), pairs beautifully with either black or winter white trousers like the Sofia Straight Pant in Winter White ($109, anntaylor.com). Keep up the masculine/feminine contrast with demure ballet flats like the Zoe Ballet Flats in Leather in Black ($70, jcrew.com) and bold reading glasses like the Bixby Readers in Hemognar ($110, caddislife.com). Potential add-ons: Petite pearl-drop earrings or a crossbody bag.

If you are meeting for a cocktail and want to appear sexy:

Natalia Pant in Four-Season Stretch in Black; Bliss Silk Resort Shirt in Blizzard Blue; Lauren Ralph Lauren Gold-Tone Pave & Color Stone Lariat Necklace in Green

Left to right: Natalia Pant in Four-Season Stretch in Black ($148, jcrew.com); Bliss Silk Resort Shirt in Blizzard Blue ($150, bananarepublic.gap.com); Lauren Ralph Lauren Gold-Tone Pave & Color Stone Lariat Necklace in Green ($58, macys.com)

Photo Collage: AARP; (Source: J. Crew; Banana Republic; Macy’s)

It’s not a great idea to go all-out-siren on a first date. A simple shirt in sensuous silk like the Bliss Silk Resort Shirt in Blizzard Blue ($150, bananarepublic.gap.com), an alluring lariat necklace like the Lauren Ralph Lauren Gold-Tone Pave & Color Stone Lariat Necklace in Green ($58, macys.com), slim pants like the Natalia Pant in Four-Season Stretch in Black ($148, jcrew.com) and a strappy but solid-heeled sandal like the Ully Lo Nappa Leather Sandal in Black ($128, schutz-shoes.com) will get the point across, subtly. (Be sure to get a pedicure! An icy shade of polish will go nicely.) Potential add-ons: A black faux-fur vest or metallic clutch.

First date recap:

Obviously, what your date shows up wearing will say a lot too. On my first one with my husband, we decided to rendezvous at a casual outdoor restaurant in Greenwich Village. I chose to wear an aqua washed-silk jumpsuit (Hey! It was the ’80s!) and silver sandals — and he materialized, to my dismay, in a singlet, shorts and running shoes, as if he was just jogging by! Sometimes we still get our messages crossed, but, happily, he was my last “first date.” Clothes say something about who you are, but not everything!

Cindy Weber-Cleary is a freelance writer, consultant and on-air fashion expert who has appeared on Oprah, The View, Good Morning America and the Today show. She began her career as a fashion editor at Vogue and was fashion director at InStyle, Glamour and Cosmopolitan.

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