What To Wear When You Are Dating At 40, 50 and Beyond

Sure you’ve dated before, but finding love the second time around can be awkward and scary. At 40, 50 and  beyond, what do you say, how do you act, and what the heck do you wear on a date so you look sexy,and not desperate? Here are 3 outfits to make to make you feel confident and look alluring in a classy, grown-up way. What to wear on a dinner date  

What to Wear on a Dinner Date

You’re a woman. Vivé la difference. You can’t go wrong in a dress!

  • Wear your dress at or above the knee and accessorize it with some flirty pieces.
  • Choose a fitted but not skin- tight dress.
  • A wrap or faux wrap dress will minimize your mid-section.
  • When the focus is your legs, avoid excessive cleavage or visa versa. One sexy focal point is enough.
  • Keep your neckline feminine by adding a drop necklace that sits at your bust.
  • Wear with a shiny pair of pumps to show off your calves. A peep toe is sexy.

What to wear on a coffee date  

What to Wear on a Coffee Date

This is one of the hardest types of dates to dress for  because you want to look cute and pulled-together, but not too overdone.

  • Try a straight leg jean in a dark wash to look slim and classy.
  • Since your legs are covered, select a top that shows a little skin (but not too much!). If you feel too exposed in a v-neck, layer a camisole with a lacy trim underneath.
  • Add a cropped jacket in an eye-catching color that compliments the colors in your top. Pinks and peaches will make your skin glow- very feminine.
  • Keep your accessories casual: a printed flat, neutral grab bag, and a long necklace pull the look together.

What to wear on a casual date

What to Wear on a Casual Date ( to a Museum, Art Show etc.)

  • Look fun and sophisticated by pairing classic staples with fun accessories.
  • Inject some spirit into a classic skirt and sweater combo with a funky statement necklace and cool watch.
  • A pair of pumps in an unexpected color shows off your spunky side.
  • This look says “ladylike” and “youthful” at the same time.

Don’t try to dress up as someone you’re not. This is especially important on the first few dates because you want your date to see you for who you are, not a contrived version of yourself. Play up what you feel are your own best features and own it! Remember: confidence is sexy. So don’t forget to be yourself and have fun with it!

Dating over 40

You are never too old to look great on a date!

And if those aren’t enough outfits to wear on a date, here’s one more. This look is from my reader, JoBee. She is her 70′s and is widowed and dating. Doesn’t she look fab? *This post has been updated since originally published in 2010 in keeping with current style. Guest Contributor for this article: Chantelle Collier.

Is Age Appropriate Dressing All In Your Head?

Of all the questions my readers send me, the one I seem to get the most is a variation on the theme of age-appropriate dressing: “Can I wear short skirts/low-cut tops/bikinis/etc. at my age?”;“Does this make me look like I’m trying hard to be young?”; “Does this make me look old?”

I call it the Goldilocks question: “Is this outfit too young, too old, or just right?”

Age appropriate dressing

photo by: Cue Ozop

I recently came across  an  article featuring a series of photos that dramatically demonstrated why dressing “age appropriately” may not be all that it’s cracked up to be. The first half of each of the seven images, by the photographer Cue Qozop, captures parents and their children wearing generationally appropriate clothes; in the second half however, parents and offspring swap outfits. The parents, in essence, are decidedly not dressing age appropriately. And do you know what? They look fantastic!! (Their kids don’t look half-bad either when they are wearing their parents’ clothes, BTW.)
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What Does An Age-Appropriate Leather Jacket Look Like?

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A beautiful leather jacket is an investment that you can enjoy at any age. The key to looking classy in a leather jacket is to find a jacket that is streamlined and more on the elegant side like … Continue Reading

Am I Too Old To Wear That?

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How many times have you eyed something cute in the store, picked it up and wondered, "am I too old to wear that"? It's confusing knowing how to dress after 40 because our bodies have changed, our … Continue Reading

Are Patterned Jeans Just for Teens?

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Hi Deborah, I love the very trendy patterned jeans and wonder if they're too young for the 50+ gals. I found a really cute pair that are wine colored with a tone-on-tone harlequin pattern. They're … Continue Reading

Florals Old Lady – Are You Kidding?

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You can’t say the words “spring and summer fashion” without mentioning florals. Whether they're the focal point on a dress or splashed all over a pair of pants, florals are a romantic staple of the … Continue Reading

How to Dress Comfortable and Stylish When You’re Over 40 and Beyond


It wouldn't be too outrageous to say that dressing casual is a daily head scratching dilemma.  Between trying to be comfortable and still look classy  and updated  sometimes it just seems easier to … Continue Reading

Poor Fit = Frumpy After 40!

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We caught you!! Are big baggy sweaters and loose sloppy pants making you look old and frumpy? Go the mirror now. Take a good look. Be honest. Baggy, poorly fitted clothes are a big problem after … Continue Reading

Are These Shoes Age Appropriate?


I got two interesting questions recently asking about shoes that may look too young?. Q. #1 Hi Deb, I was at the mall yesterday and looking for a pair of wedges to wear.  I chose these but now … Continue Reading

Can I Wear A Pleated Skirt After 40?

white sundress

Hi there Deborah, I have seen a lot of pleated skirts for sale lately. I really like them, but was wondering if I can still wear them now I am in my 50's and a little heavier than I was when I wore … Continue Reading