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9 Tips to Look Stylish on a First Date at 50 Skip to content

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9 Ways to Look Stylish and Self-Assured on a First Date at 50

Take that big leap and showcase your best self

A couple drinking coffee

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En español | So, you're ready to dive into the dating pool again at 50-plus. That first date might be a dating-site pick, a family fix up or a “let's grab a coffee” from a high school ex you friended on Facebook. Whatever the source, it's an audition. At the very least you'll get some practice and rediscover feelings and parts of yourself that may have been hidden (or lost) for years. At most you gain a new dinner companion or a blazing romance. And as Ariana Grande sings, if the first date doesn’t work, you can always bow out with a “thank you, next!” Here are nine empowering beauty and style tips to get you going.

1. Loosen up your hair

Hair is still a big part of physical attraction, but don't let thinning hair get in the way of sex appeal. Sensual hair moves. A swingy, glossy bob can be alluring — so can a cropped pixie with a just-ran-my-hands-through-it look. Count on any of the following for the right effect: beachy waves, springy curls, shaggy layers, a side part or flirty full bangs. This is not the time to pull your hair back in a tight ponytail or wear a hat. Trust three-times-married, beauty-editor me on this one.

2. Be high visibility from the waist up

You'll hopefully be meeting up in a public place like a coffee shop or cafe. Wear a scarf top or jacket that stands out in a crowd. A color that's energetic like a red is easy to spot and sends a friendly, approachable message. And text it ahead: “I'm by the bar wearing a big orange scarf."

3. Show off your best, keep the rest to yourself

Let's be honest, a waist adds appealing body definition. And if you have one, wear a belt to make that point. But if your torso isn't cooperating with crunches or your postmenopausal diet, focus on revealing your long elegant neck, your toned arms, spicy shoulders or long dashing legs. The extremities are always good eye-catching spots. Dig out those cold shoulder sweaters you bought last year, stack your bracelets, stick to V necks, or unbutton your shirt to just above the cleavage and wear leggings — leather ones are great even with a tunic sweater.


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4. Don't look like you're trying too hard

Jeans work everywhere on everyone, so have your favorites on call. Dressing them up or down is easy. A silk blouse or a V-neck sweater with low heels or pointy flats looks feminine and polished; a simple white T-shirt or crisp white shirt with sleeves turned up and rolled with leather ankle boots looks classy and classic. White jeans with a black blouse or sweater and your black belt are always memorable. A long rock-star scarf casually wrapped or draped adds just enough style. Save the dresses, heels and leather pencil skirts for later developments.

5. Have some edge

Always wear a black bra and panties — even under a white tee. (This is for you only.) Then add something a little unexpected or wild — snakeskin booties, those leather leggings (see No. 3), a slogan tee under a fitted blazer, or a buttery leather biker jacket with a bow blouse for a provocative counterpoint. A hint of dark humor or the rebel in you is not something that should be hidden, and it can also surface as big bold glasses or smoky eye makeup (see No. 7). 

A couple eating at a restaurant

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6. Look like you ... right now

Listen: It’s OK to use filters to tweak online photos — not to deceive but just to brighten skin, soften lines, clean up whites of your eyes and teeth. At 50 your weight, hair and looks do change, and these do happen: a few extra pounds here or there; new bangs or natural do instead of stick straight; short hair instead of long; or a hankering to wear flaming red lipstick. Don't apologize or explain. Just show up. A little narcissism is healthy. We're highly experienced, intelligent, informed, centered, accomplished, optimistic and attractive women. It's good to feel that power, and that includes the right to keep evolving the way we look.

7. Let your eyes speak with makeup

Listen well. A knowing glance, a wink and twinkle add a little mystery that's super attractive. Treat your peepers to a new stash of eye cream, liners, neutral shadows and mascara, and use them for a predate “pep talk.” Blend a dab of eye cream with under-eye concealer for a wide-awake look; add a subtle, shimmery shadow in sand or peach on lids; use a dark gel pencil liner at the upper lash line and inner rim for discreet shaping. Apply eye makeup even under your fabulous statement glasses. 

8. Date like you're 50

Be comfortable in your own skin and don't try to hide the history in your looks or dress like you're 25. Even in this athleisure era skip sneakers, crocs, sweatshirts, track pants and backpacks unless your first date is a hike after the gym or at a green juice bar after yoga. You don't need peak comfort. You need peak chemistry and respect for the occasion. Make an effort — your date should, too. If he shows up with unwashed hair, a dirty beard, sloppy clothes, stained teeth, or unclipped nose/ear hair, then he's not respectful. A little too much authenticity is not a good thing.

9. Say ‘Yes’ to last-minute dates

Technology has changed dating to instantaneous texts and emails to meet now. Don't stand on ceremony when there's no time to go home, shower, change, or wash your hair. Rub an ice cube over your face and lids to wake up your skin and circulation. Blot then dab cheeks and lips with a tinted balm or lipstick for a little healthy color. Tousle your hair — whatever length, style, texture; bend at the waist and rake your hands through it. Just took off your hat? Shake your head, scramble the part (if you have one) for lift. Check your bag. There has got to be a small tube of Aquaphor, eye cream, a sunscreen, or a Vitamin E capsule (or nip into the drugstore en route!). Dab any cream, salve or balm on your palms and blend on cheekbones, cuticles, brows and ends of hair. Add some scent. Haven't you got a scent strip or sample from Sephora in there somewhere? This is why you always need to carry a fragrance mini or rollerball with you. Dab throat, wrists and neck.

And remember, it's only a date.

For more beauty and style tips for women age 50-plus, check out The Woman's Wakeup: How to Shake Up Your Looks, Life, and Love After 50 by Lois Joy Johnson.

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