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What To Wear on a Date After 40, 50 and Beyond

The way you dress is a silent language that speaks volumes. That’s important to think about if you are on the dating scene. Does that mean you should dress as you always do, or step it up a notch?

Long sleeve red wrap dress 


Red wrap dress

It’s important to be true to who you are, but you also want to put your best foot forward, so dress to showcase the best version of you. If you are the bohemian type, play that up in flowy fabrics and ethnic patterns. More the traditionalist? Then stay preppy with a classic look.

Sexy types feel free to flaunt those legs or show some cleavage. No matter what style personality you are, be sure to look polished, well-groomed,  feminine, and a little sexy too.

Some clothes are like a stop signs. They make you look unapproachable, and they don’t play up your femininity.  Avoid wearing these on a date:

  • Turtlenecks – go for V-neck or scoop neck instead because exposing some skin is inviting.
  • Plaid shirts – too masculine.
  • Baggy tops- find a form-fitting, not a tight one
  • Clunky shoes with heavy heels- choose a lighter shoe with a finer heel- nothing that looks like a corporate office shoe.
  • Rough fabrics – go for silks, cashmere, and soft cotton.
  • No jewelry or uptight jewelry like little tiny button studs that are better suited for work. Sexy jewelry is loose and a little dangly.
  • Muted, dusty, sad colors like beige or industrial blue, etc.-  go for clear pastels like pink or blue, or sexy brights like red, orange Fuschia, cobalt blue.
  • Overalls – save them for yard work.
  • Stiff hair- stop with the hairspray!
  • Bare face- even a touch of lipgloss and mascara can make you look wow.
  • Outfits that cover you head to toe. Showing a little skin is sexy. You are a woman, play that up.

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 three outfits 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


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 shoes and jewelry.
  • Choose a fitted but not skin-tight dress.
  • A wrap dress is very feminine and sexy and will minimize your midsection.
  • If you have a thick waist try a sheath or tunic dress that narrows slightly at the waist.
  • When the focus is your legs, avoid excessive cleavage or visa verse. One sexy focal point is enough.
  • Keep your neckline feminine by adding a drop necklace that sits at your bust. A keyhole neckline ( as shown above on this blue dress) is also sexy.
  • Wear a pair of sexy pumps or med-high block heels to lift your bottom and show off your calves.

Fall Floral Tie Top - What to wear on a dinner date 
What to wear on a first date going for coffee

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 straight or skinny leg jeans 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!). You could wear a v-neck or open-neck peasant blouse like the one above.
  • Add some dangly earrings in an an-catching color that compliments your eyes.
  • A suede bag and booties add a velvety texture, which is inviting.
Date Black Lace up Sleeve - Coffee date outfit 
What to Wear on a Casual Date

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

  • Look feminine and sophisticated by pairing classic staples with luxe accessories.
  • Inject some allure into your look with a slim-fitting sweater and a funky statement necklace.
  • A pair of booties show off your spunky side.
  • This look says casual and sexy 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 best features and own it! Remember:

Remember: confidence is sexy. So don’t forget to be yourself and have fun with it!


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26 thoughts on “What To Wear on a Date After 40, 50 and Beyond

  1. Great post. I agree with all of it. I have a coffee date early tomorrow morning and am wearing a denim pencil skirt. I wear a casual dress for a first date since my legs are my pride and joy. Many years ago, on one of my first online dates, a date said to me that he was happy to see me in a skirt. He said all the women he had met so far wore the same black jeans uniform on dates.

    I save the black jeans for date 6;o)

  2. Hi Deborah and Glam Gals!

    Not surprisingly, Deborah, you and your talented staff have provided us gals with the most fantastic fashion ideas for various occasions.

    I especially like that you showcase the “entire” outfit, including all the accessories that make any outfit “pop.”

    Please keep all your great ideas coming! I LOVE YOUR SITE!!

    Best to all,

    1. Hi Judith, I’m so glad you like these. I just wanted to comment on the last outfit- the sweater and black skirt. The key to this look is getting a soft, light sweater to wear with the dress- no heavy, rough knits. Cashmere is best because it’s super soft and inviting. That is sexy. You want to cozy up to cashmere. Cheers! Deborah

  3. I just found this site and like a lot of the advice provided. I sometimes struggle with walking the fine line of “age appropriateness.” I am about to turn 49.. and while I work in a casual business environment with occasional up dressing for vendor events. I generally spend my time in ultra-casual clothing.. since I have acreage.. dogs.. horses.. chickens.. and they do NOT care whether I accessorize! That, I guess, is my biggest downfall in dressing. I am quick to wear jeans and boots (as in roper cowboy boots) with a knit top/T-shirt most of the time out of work. I WANT to look more put together, but I have difficulty finding clothes that I don’t think are too contrived for day-to-day use.
    Shoes have to be the worst part. I have semi-wide feet and am in an awkward 8/8.5 size. I don’t mind wearing some amount of heels.. but for day-to-day casual, wearing a flatter shoe is just more practical. Unfortunately, I have found absolutely NO flats that come anywhere close to comfortable or wearable.. unless they are the slip-on keds style (sperrys, etc.) of a sneaker shoe. They all fall off my feet.. or cause blisters. I found one pair of Anne Kleine low wedges about 1.5 inches in the heel that are very comfortable (so I bought both the black and the black/tortoise color). They are often a go-to shoe for wearing to work since they are comfortable. I am not tottering around in heels. I like to wear slight wedge or platform heights.. have a super hard time finding comfortable shoes.
    Another problem is that so many shoes are “plastic” and not leather which at least has a chance of stretching and molding to your foot a little! Oh.. yeah. I also have large calves.. to the point that the Frye boots I bought in the “extended calf” size (Jane style) barely fit over my calves.. even though I am in reasonably good shape (ok.. have about 15-20 pounds more I would like to lose.. and AM working on it.. over 45 lbs down since January). I was hoping they would fit me better once I lost weight.. but my calves seem to be holding more steady than the rest of my body, going from a size 16+ to about a ten right now.

    I did see you mention a style consultant, and I think I may try to go with the Nordstrom service. Maybe as a reward, when I reach my goal weight to pick a few pieces? I like a lot of your selections, but unfortunately, I am not spending 200 dollars plus on most pieces in my wardrobe… But, at least you show some options, and I can try to find similar articles at my lower price point.

    I like that you don’t have set parameters in stone about what people can and can’t wear.. maybe except the horse hoof platform shoes that look appropriate on pretty much no one except strippers. My then four yo stepdaughter tried to buy someone time, and we made her take them back (much to her chagrin).. but seriously. WHERE was she going to wear them??? She does ‘t go clubbing at that age, and I have never seen girls wearing them out anywhere.. so they must have them in their closet to covet.. and we don’t have closet craving money..haha. She needs d stuff that she could WEAR. The fact that she has an, unfortunately, larger foot.. those shoes looked pretty silly!

    Anyway, I just wanted to give you props for all the excellent advice. If you h ve any magical lower flat shoes or midheight wedge heel options that you think are particularly wearable and comfortable. I would love to know about them (even if they are somewhat spendy.. shoes are one thing I can consider spending a little on since feet don’t change size too quickly)

  4. Wow, Jolee is HOT!! What a fabulous role model! I’m 55, and she gave me hope and a great example. Thanks for sharing.

  5. Although I am 5’4″ and weigh 112, my body is changing, not in a good way! I exercise at the gym and go on long walks, but I am thickening in the middle and have a growing roundness in my middle :( I couldn’t wear a light sweater or T over a pair of skinny jeans, especially not with a belt! I wear similar clothing to what your mom has and even have a similar long jacket from Zara! However, I need to make sure my sweaters camouflage my middle section. What are your mom’s diet tips? I’d like to turn this situation around:)

  6. Jolee IS Age-mazing!!!! She would look good in anything! She has the flattest abs and the youngest-looking face EVER!!! Oh yes…her outfit – it’s nice:)

  7. OMG! She’s beautiful! When I grow up, I want to be like her.
    I’m also recently widowed and trying the dating scene again. Thanks for the tip!

  8. I love her scarf! Any idea of where she got it?! Jolee is an inspiration…I am 54, and I want to look like her when I am over 70!!

    1. Hi Kelly, I will ask her about the scarf, but I know she has had it for over six years. She has an extensive collection of scarves and loves to wear them! This one has a little fringe, giving it a nice twist and some movement to an outfit. These types of scarves are not easy to find but an available if you go to a higher-end store or a lovely boutique.

    1. Hi Saretta,
      Yes, she is def. An inspiration…and the best part is, she is a sweetie too!! She is a shining example of when you eat right, partake in regular light exercise, and keep her wardrobe updated; all add up to being a lifelong Glam Gal!!

    1. Good luck, Eleanor! I hope you find your perfect partner, but from what I have heard, it takes a lot of work and weeding! Making sure you are dressing the part is a small part of finding your soul mate, but an important one is that you are sending the right message. Just getting that first date means that your first impression is a true one.

  9. I about fell off my chair when I read this woman is over 70! The chair was quite tall too! She looks fantastic, but she is NOT your average 70-plus-year-old. It is youthful but classy, but unless you look THAT good, I won’t try that look at that age. I am hoping for some fashion for the “average” woman….you know, 5’4, 140-150 pounds… far, I only see women who look better than the average woman – and that doesn’t help me “relate” to the clothing…or the “look.”

    1. Hi Kathleen,
      LOL… Jolee is not typical, and I agree she has a super figure, but she also dresses to flatter her figure! It is incredible how you can put on different styles of jackets, tops, and scarves and create an “illusion” of being thinner and taller than you are. There are several books out that show “how to” (see this link) that we recommend. I do hear your plight Kathleen; however, If you were to take some of the tips from the post, you can still apply them to your wardrobe. I like to put pictures of “real” women, but they are hard to find.

  10. I think this woman looks hot for a 70+ lady interested in dating. However, I’m a 47 year-old technology professional by day and I wouldn’t dress like this for a date. To me this looks like a business-professional look and I think my date would think that I may be coming from work if I wore it on a date. It does look more like something you would wear to meet up with other women. It’s classy and nice. There is nothing wrong with this look and it’s age appropriate, but I’m just wondering if you can comment on dating looks for someone in their 40’s.

    1. Hi Patrice,
      You are right, one look is not for everyone! I’ll continue to do more posts like this to show lots of different looks that are age appropriate!
      Thanks for commenting!

  11. Great advice. Do you have any suggestions regarding online dating after 40, as in any particular “online dating after 40” interaction tips, to make it to that actual world date?

  12. She looks fantastic!! This is the same situation I am facing, just a bit younger. What style of shoes is she wearing? Would this look work for a very casual business casual workplace? Any links to this blazer?

    What a great look – I love it!!!

    1. Hi Jenny,
      The jacket was purchased in the fall, and she has some fabulous heels. (I will see if she can send us a photo of them). As for this outfit, working for a very casual business workplace, I would say, take off the jacket, then…absolutely, YES!! You might go for a leather jacket instead.

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