Help me dress my mid-40s self to start dating again
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Anonymous
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I'm 44, a size 0/2, 5'5", athletic build, I'm in good shape (and getting in better shape recently) but still have a tiny bit of loose skin on my belly from my pregnancy 8 years ago. I think I look my age but good for my age. Not a ton of wrinkles but my face looks "mature." I'm at peace with that and have figured out makeup for it to look my best. Getting a new cut (longish bob) soon and have settled on regularly dyeing my hair a darkish blonde to cover grays. I tend to gravitate towards a kind of natural, athletic look. But back before I had a kid, I was very into fashion and jewelry. But never heavy makeup or anything too fussy.
I've been WFH since Covid and between that and motherhood, have totally lost touch with how to dress like an adult woman who is openly dating and interested in men. I've lived in either comfort clothes or a "mom uniform" (jeans, t shirts, fleece jackets, sneakers) for most of the last decade. Even my "going out clothes" (I do go out, with friend) are not sexy in any way -- comfortable loose dresses and fun jewelry, cute flats. I do not want to look desperate. I don't want to look like I'm trying to be 28 (or even 38). I think I'm actually pretty attractive and in good shape for my age, and I would like to show that off a bit. I'm looking to date men around my same age (single, divorced, widowed, with or without kids, I'm open minded). I have NO IDEA how to dress for this. I feel like most of my clothes scream "WFH mom" and do not communicate that I'm on the market. The last time I dated, I was wearing skinny jeans with high-ish heels, fitted tees and tanks, delicate gold jewelry. Or fitted dresses to the knee with heels. I am unsure I can do heels again but willing to give a short heel a try. DCUM, be my stylist. What would you have me try on as potential date-night outfits? Keep in mind the target audience (men in their 40s) and the fact that I want to look hot but not like I'm trying too hard to look hot. I am at your mercy. |
Anonymous
| OP again. I wanted to add, since we're talking clothes here and fit matters -- I'm small busted (A cup). What I have is still pretty perky though -- I can get away with no bra in a lot of clothes though I have been afraid to actually do this for years because I don't want to embarrass my daughter. But she's not coming on dates with me! |
Anonymous
| I'd go to a Tuckernuck store and ask one of the sales people to style you. They have great clothes for women in their 40s in a range of prices. Being styled in person is really the best way to find what you are looking for. |
Anonymous
OP here. I actually have some stuff from Tuckernuck, but I don't think it reads as date attire. Like a lot of the dresses lean either "society wife at a pool party" (and don't get me wrong, I love a caftan, I have several) or kind of preppy short dresses that feel too buttoned up and preppy to wear on a date. I am definitely open to working with a stylist, but don't think Tuckernuck is hitting the right note. I want the more grownup, 2024 version of well-fitting jeans and a "going out top" like what I wore on dates back I the 00s. What is that? |
Anonymous
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I would go to the nearest allsaints. some skews a little young, but there’s enough stuff that would work on a fit 40 yr old.
https://www.allsaints.com/women/clothing |
Anonymous
Oh lord. Tuckernuck is not what is needed here. |
Anonymous
| How about Reiss or Karen Millen? |
Anonymous
| Fitted dresses always look nice. |
Anonymous
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My dear OP.
Please. Believe in yourself. Wear what makes you HAPPY and CONFIDENT, because this, above all else, is what attracts people. Would you like to dress in the same style as when you last dated? I promise you that you will look great. Would you like something else? Look at websites and their lookbooks. Peruse a Vogue catalogue to see what the outrageous looks like now (and how you can reduce it to approximately normal streetwear). I'm the same age and the same size. I wear mini skirts, I wear short shorts (nothing hangs out), I wear long boho dresses, I wear clothes that highlight my smallish waist, I wear baggy trousers, I have a range of fun tops with interesting prints, or interesting structure - my favorite is the corset-style one. I want to have fun with clothes in this decade of my life. Also, I'm happily married. I would wear these clothes regardless of my marital/dating status. They make me HAPPY. You only have one life. |
Anonymous
My version is well-fitting bootcut/slight flare jeans (I like brands like Paige, Frame, and AG) with a silk button-down (I prefer the 3/4-sleeve ones from L'Agence and get them from The Real Real) and low heels. I've worn some version of this out on dates and drinks with friends at a nice bar/restaurant. I also have a very classic, minimalist black leather jacket from AllSaints that I wear over a fitted t-shirt with the same jeans/heels. For summer, I tend to go with fitted (but not tight) midi-length blue, black, or white denim with t-shirts and sandals (again with a low heel - I'm short and need some height but can't swing 3" heels anymore either). |
Anonymous
Thanks, I'll check this out. |
Anonymous
Can you give some examples of tees you would wear on a date? Would also love some low heel sandal recs if you have them. |
Anonymous
| I think you’d look great in some Club Monaco and Anthropologie, whether more classic or more boho, mix and match the pieces. I think you’d find something in both stores. |
Anonymous
I get what you're saying, but I do wear what I want and don't have trouble being myself. But it has been a really long time since I got dressed with the thought or intention of being attractive to a man. I'm just looking for ideas here to get myself in that mindset. I want to be able to walk into a room and turn a head again, but I feel like if I dress the way I did in my 20s, it won't suit me anymore. So I'm trying to get a sense of what people are wearing in this context now and then I can figure out how to make it feel like me. I just need a jumping off point. Also, no offense, but I think dressing for a first date is different than dressing as a long married woman. We're just at different places in life. |
Anonymous