How to dress for a first date at 40?

by Sylvia

How to dress for a date at 40

First of all congratulations on your date! Whatever the circumstances, it’s wonderful to date at any age, but I can imagine that it is really interesting when you are 40+. By that time you already have so much life experience and you know what you want (I hope). You can potentially have amazingly interesting conversations.

Dressing for confidence, 5 key things to remember!

Let’s assume that you are meeting someone for a date for the very first time. Your objective will be to get to know this person and also to make a good first impression. Here are some of my tips:

1. You will want to show this person the real you. So dress to express who you are. Showing and feeling confidence will make you the most attractive. You will feel far more confident, if you dress in something that makes you feel comfortable but that also makes you feel sexy. It you know your style statement, then that can help you in making sure that the outfit expresses the real you.

2. Don’t go too sexy! I’m a firm believer that you look far more appealing and sexy if you show less. You also don’t want o look to ‘willing’ on a first date. Better to keep things a bit mysterious.

3. Go for something comfortable. Something you will feel totally relaxed in. Comfortable does not mean ill fitting or unflattering. Make sure your outfit fits you well, but stays in place. Nothing is more unsettling that having to fiddle with your bra straps, or making sure that your skirt stays in place.

4. Opt for something you have worn before and that you know you feel great in. As mentioned, you want to show confidence and concentrate on getting a great conversation. You do not want to worry about a new outfit that just doesn’t feel right.

5. Choose your underwear wisely. If you followed the tips above, you will probably not wear anything too tight or uncomfortable, so choose some nice looking underwear (no need for shape wear!) that matches. Knowing that you are wearing some wonderful underwear, may just give you that extra glow and confidence.

Some of the outfits I would recommend

1. Well fitted black or cobalt blue pants with a well fitted skirt that you have buttoned all the way up. Decorate with a nice collar.

2. Lose fitting jersey dress with great draping. Comfortable and it covers all of your ‘problem’ areas if you have them.

3. Tight jeggings or snug pants and a tunic. Combine with a hat for that extra touch!

I hope these tips help. If you are having a date coming up, I hope it goes really well.

Which outfits would you recommend for women having a first date after 40?

{ 8 comments… read them below or add one }

1 Suzanne

I sincerely hope I never have to go on a “first date” again. I and my 4 closest friends have each been married for 23 to 28 years. 🙂 I have no experience with dating. But I love what you said about dressing to show your confidence, not showing too much skin, and making sure you are comfortable in your outfit – physically and mentally. Be your best self and you will attract the person you deserve. I like all four looks you posted above and would wear those clothes. They are simple and clean but the accessories make them current.


2 Sylvia

I’m happy I got it right in your opinion. It’s actually quite fun to think about what I WOULD wear on such an occasion..


3 Cynthia

Ha. I have blind dated within the last year (at 43) and, yeah, it sure is interesting. Top priorities until you know someone are full coverage, freedom of movement and good ground connection through your feet. My ideal first date outfit is a fitted but not movement-constricting jacket, over a pretty top or graphic tee, and pants or jeans with a heavy belt. I wear comfortable, flat shoes that stay on my feet securely — hip leather sneakers are my favorites. Outfit #3 would do, except for the shoes, but I’d be a little overdressed for the socioeconomic circles I run in.


4 Sylvia

Thank you so much for your feedback Cynthia! It’s great to hear from someone who is actually dating at the moment. Great advice and good luck in finding someone special!


5 The Style Confessions

I too haven’t gone on a first date in 20 plus years, but I think your advice is sound. I think if I had to go on one I’d be a little glam and wear a drapey knit jersey dress. I would want to be sexy without being too sexy.


6 Sylvia

Great advice. Thanks for your input Heather!


7 Bella

I have been married 20 years and I still try and dress like it was our first date when we go out (even for a lunch date) Love this post.


8 Sylvia

Thanks for your feedback Bella Curious to know how you dress then.. Do you follow some of the directions above or are you going for a more sexy look?


Leave a Comment

Previous post:

Next post: