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?
Feature image by Sydney
Want to get more articles from 40+style in your inbox, subscribe here.
You can also connect with 40+style on Facebook, Instagram or Pinterest.
Support 40+style by using the links in our articles to shop. As an associate for Amazon and many other brands, we receive a small commission (at no cost to you) on qualifying purchases which enables us to keep creating amazing free content for you. Thanks!
For the love of god, wear something the guy finds attractive. Baggy anything is not attractive, it makes you look fat, or that you’re wearing a bag. Do not use jeans as a go to. Jeans are getting repulsive because everyone wears them everywhere when they’re not even appropriate for everything. Never once, nor will I, wear jeans on a first date. That screams LAZY! Jeans are casual. Some first dates can be, too, but even still, casual doesn’t always mean jeans and t-shirt. You’re dressing for a date! Not to impress your friends, or look like you just rolled out of bed. Some of these outfits are downright hideous and frankly, if I were the guy you’re meeting, I’d say, “see ya” if I saw you come through the door wearing this stuff.
You’re not dressing for yourself on a date. You’re dressing for your date. What you find attractive and what the guy finds attractive are two entirely different things.
Do NOT dress like a streetwalker on the first date, either. You’re not a teenage girl falling in love for the first time. You’re a sophisticated, experienced woman in your 40’s, dress like it.
I get the whole “comfort” thing, but comfort also means casual most of the time. Again, a date isn’t about you. It’s about your date. Wear something he may find appealing.
You’re on your date to make an impression on a person who may also be your next relationship. Dress to impress. Dress for him. It isn’t always about you.
I am so sick of this ultra casual, ultra “i don’t care about my appearance” thing we have going on with fashion these days.
“Anything goes” is getting old fast.
Here’s a fun fact: the first thing I man notices about you is not your outfit. It’s your face and your body. Make them look nice by wearing makeup properly and clothes that are flattering.
I’m still single at 46 (too busy for a relationship and dating is fun) so I go on a LOT of first dates! I do have a lot of life experience, but I still don’t know what I want…I’ve dated men of all ages, shapes and sizes and can’t seem to pick just one (or maybe it’s because there are so many great men out there).
I tend to not think about how sexy I am dressing because I’m comfortable in my skin and as an athlete am frequently stripped down in public places and am used to having strangers looking at my body. I’ve stopped caring what people are thinking else I’d have massive anxiety and body issues. Who needs that in their life?
Totally agree with points 3,4 and 5! Being physically comfortable is key–especially an old favorite! And point 5: wearing nice underwear…I don’t know WHY this makes me so happy. If the conversation starts to get boring, I think about the cute undies I’m wearing and can’t stop smiling.
Depending on the time of year, I have four go-to outfits:
– a loose chiffon tank in a color that looks great on me (burgandy) with black leggings and cute black boots. It’s cute and comfortable enough to wear to practically anything (museum, spontaneous midnight hike, dinner at a nice restaurant, go-carting, dancing at a club)
– a darling floral print sundress. Great for salsa dancing, dinner, brunch, any non-active activity where I want to look cute and feminine.
– khaki shorts and white tanktop. Anything that is a bit more active–rock climbing, backpacking, kayaking.
– a black spandex dress that you feel gorgeous in that won’t shift, ride up, wrinkle, show stains (for me it’s a cap sleeve, scoop neck minidress)
Thanks for sharing these tips! They were really great!
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.
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?
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.
Great advice. Thanks for your input Heather!
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.
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!
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.
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..