Sexy First-Date Looks For Midlife Women

If you’re looking for a date-night outfit that’ll impress him without looking inappropriate for your age, follow these fashion tips designed exclusively for women over 50.

By Jane Ganahl

o, you’re a woman over 50 and getting back into the dating game. Maybe you ended a long-term relationship awhile back and feel ready to start looking for a new partner. Or perhaps you’ve connected with someone whom you think you might really like after a going through a dating dry spell, and are excited about
Sex appeal is about more than just the clothes you wear.
meeting this person for dinner.

The question now is: What should you wear? You want to look sexy — but the last thing you want is to look 1) easy or 2) insecure by going for the “Las Vegas cougar” look. (Even if you still have the legs for a miniskirt, choosing that look over something more elegant means that others are bound to make assumptions about you.) But rest assured, ladies: It’s not only possible to look sexy after 50 — it’s actually not all that hard to pull off.

Three ways to start from the inside and work your way out
1. First, assess your inner beauty traits. Sex appeal is about more than just the clothes you wear. Before giving your outer self a makeover, begin with remodeling your interior. If you’re feeling down about yourself because of a recent romantic failure or the effects of gravity on your once-perky frame, take a moment to assess your real strengths. You’re smart, you’re capable, and now that you’re a bit older, you’ve entered what Gail Sheehy refers to as “the age of mastery” — and that means you have a lot to offer a potential mate.

This self-confidence check is important, because as Christian Dior himself once noted, “no beauty is attractive without zest.” Nothing is sexier in a woman of any age than confidence — and it’s doubly important for attracting the opposite sex as we grow older.

2. Loosen up and be willing to laugh things off. Another thing you need to have is a healthy sense of humor. Middle-aged women seem to have the reputation of being driven, “Type A” personalities who need for things to be perfect at all times. Show men that you’re not going to be labor-intensive by looking for humor in all things. Laugh with gusto — it releases endorphins.

3. Leave your life story off the table for now. Avoid making the mistake young women typically make while they’re dating of feeling like you have to tell someone your entire life story during that first encounter. By now you have a whole life-long story to relate — but let that river of information flow slowly, please! It’s important to retain a little mystery.

First-date wardrobe tips for women over 50
In order to find out which looks highlight a midlife woman’s sex appeal without going overboard, we interviewed designer Braeda Horan, owner of the Northern California business, Restyle Your Look (a company that specializes in revamping the wardrobes of successful women, as well as color consultations, wedding consults, shopping trips and many other fun offerings). Here’s what she told us:

1. Showing off some skin can be sexy — but give it a healthy glow first. “The important thing for a woman on a first date is to look alluring… but not like she’s for hire,” says Horan. “Miniskirts and major cleavage scream desperation and insecurity. It’s okay to show a
Knowing your flaws is just as important as knowing your assets.
little skin — whether it’s your legs, chest, arms or back — but not all at once.” Horan, a striking 50+ herself, recommends that each woman seeking to impress do a self-assessment of her best features before choosing a first-date outfit. “At this age, no one is perfect. But each body is beautiful in its own way, and everyone has an asset worth focusing on — whether it’s your eyes, your arms, your legs, etc. Decide what your best assets are, and then capitalize on them.”

2. Dress for your figure, and choose elegant, age-appropriate clothing. Horan maintains that men don’t necessarily want “skinny women,” and says what really attracts them is “confidence and a healthy glow, so taking good care of yourself is as important as the clothes you wear.” Horan, who was formally trained in England in fashion design and apprenticed with one of the couture houses in Paris, is a big fan of elegance rather than brassiness. “If you dress like you’re in your twenties, you’ll look like a cougar,” she added. Conversely, “comfort is important at this age — but if you go too casual, it will look like you don’t care,” cautions Horan.

3. A pop of color (or some striking accessories) can make any outfit memorable. As Coco Chanel famously said, “I don’t understand how a woman can leave the house without fixing herself up a little — if only out of politeness. And then, you never know, maybe that’s the day she has a date with destiny. And it’s best to be as pretty as possible for destiny.” Horan recommends conservative but elegant clothing peppered with striking accessories. “I’m a big fan of red shoes and red handbags,” she laughs, adding: “accessories are like the ribbon on the package. A colorful necklace or a great scarf is always smart.”

4. Petite women should avoid chunky, oversized accents, and kitten heels are a smarter choice than stilettos. If you’re on the smaller side, Horan says, don’t overload yourself with a heavy bag or too much jewelry. And as for the all-important shoe question? Horan says “no heels over 4 inches” — after all, “you want to walk elegantly, and after age 50, women’s feet tend to lose some of their flexibility and padding,” she counsels.

5. Dress strategically to draw attention away from any self-perceived flaws. Knowing your flaws is just as important as knowing your assets, according to Horan, because understanding both will help you select clothing that’s right for you. “If you have big hips, wear a flashy necklace, which will direct their eyes upward,” says Horan. “If you have a short waist, choose a long top with a skirt and a belt that’s worn loosely on the hips,” she advises.

And it’s not always important to go for expensive brands, either. On the day we chatted, Horan was wearing an eggplant t-shirt from the GAP paired with an eye-catching necklace and form-fitting leather jacket with a simple pair of jeans. Clearly, Horan has had plenty of time to learn what looks good on her.

More than anything, says Horan, “you should have fun with finding your style — take some chances and see what works!” Eyes twinkling, Horan adds: “When you feel festive, you’re bound to feel confident — and that can lead to a fabulous date!”

Jane Ganahl is author of Naked on the Page: The Misadventures of My Unmarried Midlife, editor of the anthology Single Woman of a Certain Age, journalist of two decades, and codirector of San Francisco’s Litquake literary festival.
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