What should I wear on dates?

December 29, 2023 1:09 PM

I am 42 and hoping to go on some dates. Can you suggest some clothing?

I feel like I have so many clothes but they're not cute or flattering. My shoe options are limited bc of foot issues but I have Birkenstock mary janes and a pair of black ankle boots. My weight has fluctuated a lot and currently I'm about a size 12-14 and wish I did not weigh as much. I would wear anything except a short skirt w no leggings/tights. What are some stylish/current clothing options? I don't like white or red but would wear any other color pretty much. I would like to spend no more than $150 per item but less would be great! Brick and mortar or online options are both fine. Thank you!!

posted by bookworm4125 to Clothing, Beauty, & Fashion (23 answers total)

Something in a wide leg/cargo/baggy style, skirt or pants or jeans. They're on trend and men generally find them unattractive, which is an asset in my opinion because it will allow you to weed out men who seem to need to share that they feel Some Kind Of Way about your aesthetic choices.

It's also a look that I personally happen to feel cute and comfy in, so I'm happy.
posted by phunniemee at 1:22 PM on December 29, 2023 [6 favorites]

What clothes do you feel the most comfortable, joyful, and confident in? Wear those—especially the comfortable part! I don’t know how much you need to worry about the clothes being stylish/current, because at some point this person is going to see all the rest of the clothes you wear and hopefully not care or judge if they’re old or unflattering or whatever.

But if you want to buy something new to give you confidence and it would make you feel better to feel like your new clothes are trendy, here are some styles I’ve noticed lately: I think baggy clothes are on trend, especially wide-leg pants or straight-leg jeans. Even baggy on baggy, like a big sweater over wide leg jeans. Cargo pants/skirts, as phunniemee noted. Cropped tops, either the fitted baby tee style or big and wide like a cutoff sweatshirt. Birkenstocks and Mary Janes are both on trend too, so those sound great. Long pleated skirts. Slip dresses, often over a turtleneck or tee. Polo-style shirts and sweaters. Half-zip sweaters. Vests or sweater vests worn as shirts. Brown as a neutral. Corset-inspired details. Square necks and square toes. It’s all very 90’s right now. Window shop at fast fashion sites and you’ll get the vibe of what’s trending.

But if you’re dating people the same age as you, and not, like, 20-year-old fashionistas, you may find that the current trends look weird to them in any case, so chasing current styles might be fruitless if it’s for their sake. Wear what you like and what makes you feel good and that will be the most important thing IMO.
posted by music for skeletons at 2:10 PM on December 29, 2023 [3 favorites]

Response by poster: I would love specific suggestions of stores if people have them. The clothing does not have to be current for a 20 something year old, but for an early 40s person.
posted by bookworm4125 at 2:41 PM on December 29, 2023

I am in my early 40s. I guarantee no one you would be dating cares if you are on trend.

What is your body shape like? 12-14 doesn’t really tell much about how things are distributed, and different clothing lines support different bodies.
posted by corb at 2:56 PM on December 29, 2023 [2 favorites]

Agreed that on-trend doesn’t matter to anyone age-appropriate you’d be dating. I’m not really sure why this answer came so strongly to mind since without knowing more about your style it’s hard to know for sure, but you can get Diane von Furstenberg dresses secondhand on apps like TheRealReal for about $150, an in my experience they go decently well with ankle boots on a wide range of body types; they feel snazzy but not super fancy to me…though I’d probably be in jeans for 99.999999999% of first dates I’d go on, that’s the kind of dress I’d wear to a
nice dinner on a second or third date.
posted by Merricat Blackwood at 3:04 PM on December 29, 2023 [1 favorite]

I'm roughly your age and size. The newer stuff I have that looks cute and good is mostly from J Crew Factory (Factory is key, both for $$ and also I feel like they have better stuff than regular J Crew) and Boden, with a sprinkling of Old Navy -- they have these satin button-downs that are cute as hell so I bought two colors, and tucked into some wide-leg jeans it's my standard going-out look these days. I've also been doing plaid skirt (JC Factory has a bunch), colored tights, and big sweater for something femme-ier. Daniel Rainn has some cute blouses but don't buy direct from them, their consumer-side service is a disaster.

Hugely seconding phunniemee on the wide-leg jeans, I cannot overstate my delight that these are back in style.
posted by goodbyewaffles at 3:50 PM on December 29, 2023 [2 favorites]

I'm 43 and not dating currently but I feel you! (I'm around size 8-10, depending ...)

One thing that's on trend that works is mixing of textures. So in your case, I'd do a satin midi skirt (if you're not opposed to Amazon, I like this one) in a color you like and then a neutral chunky sweater (again, Amazon). Tights and whatever shoes you're comfortable in will work here.

I like this sort of look because it feels modern but also lived-in and it's easy to pull off. (I've worn variations of it to a few occasions recently.)

The trend for accessories seems to be more minimal jewelry but if you have something you like, wear it. Me, I've been collecting vintage jewelry so I'm going to be wearing that.

I will second Old Navy is having a good run right now. I did link to two pieces from Amazon's The Drop line. A lot of it skews younger but their "staples" do have good basic pieces that are just a bit updated for more recent trends.

(But yeah, I think so many of us around this age are adrift and have no idea what to wear anymore.)
posted by edencosmic at 3:55 PM on December 29, 2023 [3 favorites]

As someone your age, though not going on dates, I heartily n'th the big pants concept. Baggy jeans, wide-leg black pants (I have these and recommend them!), cargos - whatever you like and feel comfortable in. The bonus with big pants is that your shoes barely matter so you can focus on your feet being comfy! To top things off, you could go with a sweater or top you already have and like since you probably have at least some tops you like and both baggy and fitted tops work with big pants, or more romantic with a pretty new top from someplace like Reformation.

I feel like I'm the one person in the world who looks bad in wrap dresses but strongly second the idea of a DVF wrap dress - they're super flattering on most people and are widely available on all the secondhand websites (thredup is usually rich in options). DVF also makes cool reversible dresses but they're super expensive ($300+ even on sale but worth keeping an eye out for if you're looking at secondhand options).

I also like a miniskirt with opaque tights and a big sweater when I want to look nice but not super dressed up. That would work with either of your shoe choices and you probably have some of the pieces already.
posted by snaw at 3:56 PM on December 29, 2023 [1 favorite]

Also, The Kit is a wonderful label for brightly colored/patterned statement pieces that aren't too expensive.
posted by snaw at 3:58 PM on December 29, 2023 [1 favorite]

depends on your aesthetic if these will work for you, but here are some store suggestions. These are the bougie versions in general—honestly I find stores like Target or Old Navy generally have good, cheap versions/knockoffs of many higher end styles.

More basic/preppy:
Madewell
Uniqlo
J Crew
Boden
Everlane

More colorful:
Big Bud Press
Anthropologie
Free People
Gudrun Sjoden
FARM Rio

More high femme:
Rouje
Aritzia
Sezane
Reformation

Without knowing your style it’s hard to make suggestions—more edgy/goth/rock ‘n’ roll? More tailored/dressy? More comfy? More twee? If I were doing this in your budget I’d probably pick something like this dress and pair it with the Mary Janes and a jean jacket or sweatshirt or something. But that’s me.
posted by music for skeletons at 4:13 PM on December 29, 2023 [4 favorites]

It might be a good idea to see if your local mall or local department stores offer personal stylists for creating a few outfits for dates! It might take some of the pressure off "creating" outfits and having someone throw together outfits that are flattering, but might not be items you'd naturally notice in stores.

(Personally, I wouldn't wear clothes I found ugly to weed-out potential duds. It'd just make me feel even more uncomfortable/self-conscious about the entire dating process, but that's just me!)
posted by VirginiaPlain at 4:26 PM on December 29, 2023 [3 favorites]

I was in H&M today, and saw quite a few cute things that don't break the bank. I'm 48 and roughly a 12-16, depending. JC Penny's sometime has nice stuff too. I love a fit and flare dress.
posted by kathrynm at 4:53 PM on December 29, 2023

I'm your age and not dating, but have recently done some shopping. I have found Boden dresses super flattering and versatile. They don't look as frumpy in person as they do in the catalogue. They have free returns, so order a few and see what you like.

I was also suggested the brand Rafaella, which makes very inexpensive pants that are also flattering and comfortable, so worth trying for mixing high and low.

(And maybe I'm retro, but I think on a first date you want to look and feel really good and comfortable, whatever that means for you. It sets the tone for the rest of your dating time with that person.)
posted by luckdragon at 5:39 PM on December 29, 2023

I think it's fine to want to wear something fashionable without that implying that you are like, an immature slave to fashion or something. People in their 40s are not all madly free wheeling with no influence from the fashion world. It's just a different fashion.

Everlane or Madewell have nice dresses that I think are comfortable, stylish and go well with flats. Madewell is a bit more date-ish while Everlane is more low key.
posted by jojobobo at 8:04 PM on December 29, 2023 [3 favorites]

Also, to fancy up and outift I think ensuring that you wear some jewellery and a bag that matches in some way tends to make ppl look a bit more put together. Fwiw!
posted by jojobobo at 8:09 PM on December 29, 2023 [1 favorite]

My advice is boring but accurate: wear WHATEVER is clean and makes you feel comfortable. If that's new clothes, then cool! If it's your current clothes, then great! I am in your same demographic and I have dated peers as well as people who are older and people who are younger. The bottom line is that it does NOT MATTER. The great thing about getting older and dating is that we can be ourselves in every way: this can make it harder to find a match but also easier to find a good match. Step up your wardrobe if it's what you want but please do it for you! Are there any local friends you can ask to do a closet review? That's where I'd start. Or if you work in person and you're genuinely friends with someone at work, you can tell them you're wanting to step up your outfits: are there any pieces you currently wear that they like? Anything they'd recommend you add? (Note there's no negatively about stuff to get rid of or avoid!) You can also go to any store -- I like JCrew for this -- and try on a few things you like, then get a friendly and attentive salesperson to give you feedback. And a good salesperson can be any age, any style, any gender, etc. and give you kind and helpful tips!

I am taking a break from dating but I dated like over a hundred people these past few years. I saw a video about a 40something woman getting ready for a first-date and it was ridiculous in that she was going far beyond -- fake eyelashes, fancy tight dress, etc. Had the video merely been titled "Dressing up to go out and have fun!!" it would have been cool but I was sad to see the level of effort. I date people of all genders and most people look nice enough on dates but, I guarantee you, that if you're dating 40something men, very few of them will be going all out nor would they expect you to. You are already beautiful and perfect as is -- we all are!
posted by smorgasbord at 8:31 PM on December 29, 2023 [4 favorites]

Also, for all the shit I have been through in dating as a thin stylish younger person and chubby not-so-trendy older person, NEVER EVER has anyone been critical or mean about my clothing choices. Sometimes I'd dress more revealing and other times more conservatively; sometimes I'd wear nice sneakers and other times heels. It did not matter!! I still wear skinny jeans sometimes because they feel like a hug and highlight my curves. If baggy flowy clothes are your thing or something you're into, go for it! But nothing wrong with your favorite (skinny) jeans and a nice top. You've got this!
posted by smorgasbord at 8:36 PM on December 29, 2023 [2 favorites]

This might be a good time to try an online clothing subscription such as Stitch Fix. I haven’t used them in a few years but in general I’ve had good luck getting things that fit me well and looked nice. You could also work with a personal stylist (I have no useful recommendations, I just know they exist).

For a dating wardrobe, you’ll also want to consider the kinds of dates you want to have and what you want to convey. Exploring your personal style can be a fun and interesting exercise.
posted by bunderful at 6:33 AM on December 30, 2023 [2 favorites]

If you want to invest in a personal stylist, Fashivly looks interesting and is something I plan to do for the spring/summer (which are the harder seasons for me to style myself). You pay a fee and they create personalized "looks" based on your age, location, body type, budget, kind of thing you're dressing for (home/work/dates/etc) and your personal style goals. The looks do not include the clothes themselves but each item is linked if you want to buy it. I've seen people also include pictures of clothes/shoes they already own and love so the stylists can show them new ways to wear them.
posted by misskaz at 10:23 AM on December 30, 2023 [1 favorite]

Nthing wear what makes you feel your best, whether it is old or new.

Adding to brands to check out, try Universal Standard.

If you need some inspiration on putting outfits together, I really enjoy Allison Gray's blog and socials Wardrobe Oxygen
She's a Gen-X, curvy petite and does a great job of putting together outfits that are grown up yet modern and comfortable. One caveat, she's not afraid of color and pattern.
posted by socrateaser at 12:45 PM on December 30, 2023

I met someone one whose masks always matched the rest of the outfit, it looked really great. Here are some kn95 masks that come in different colors. They have high reviews for comfort. I also saw someone draw decorations directly onto their n-95.
posted by aniola at 3:47 PM on December 30, 2023 [1 favorite]

Response by poster: Wow thanks everyone! Amazing suggestions and thanks for all of your support--so kind. I'm an hourglass shape who used to have a more well-defined waist.
posted by bookworm4125 at 4:24 PM on December 30, 2023

So as an hourglass shape with *a* waist, even if not as well defined anymore, (I am this shape and I feel you), what I have found the best is having dresses with defined waists tailored for me by places like Eshakti. They tailor by a detailed series of measurements, so are able to get more close fitting clothing even in abnormal sizes (even leather now!) They also have a ton of wrap dresses, and frequently have very nice things on sale. It is well within your budget.
posted by corb at 8:08 PM on December 30, 2023 [1 favorite]