What to wear on first, blind date?

January 22, 2015 3:51 PM

Haven't gone in a date in 10 years, don't know this guy, and I can't figure out what to wear!

Last time I dated, on a first date--a drinks date, rather than dinner--I would wear nice jeans and a flattering shirt. But I was in my mid-40s then, a different era. I am now in my mid-50s with a very different body. I was fat then, and still am, but everything's shifted and I'm still figuring out what looks best on me.

My life in the last few years has consisted of being a student or hanging around the house. Almost never have dressy or formal occasions and never have sexy ones. My uniform has been baggy boyfriend jeans with tee shirts and with a cardigan or hooded sweatshirt in the winter.

My options for the date are the following:

Bottoms
1. New pair of mid-wash, straight-cut, flattering blue jeans
2. New pair of black, boot-cut, flattering black jeans
All other pants are way too casual or not as flattering (e.g. boyfriend style corduroys). Only skirt is short, pencil-shaped denim. Doesn't feel right.

Tops
1. New black cotton button-up, very flattering--loose but slim cut.
2. Dark red more feminine button-up shirt with lace insets. Pretty and good color on me, but kind of boxy and maybe reads a tad office-y?
3. Mustard yellow button up shirt with nice details. Again, nice color, but boxy and loose and slightly too long to be entirely flattering.
4. Not satisfied with any other options. Most stuff is loose, baggy t-shirts or pilly, bagged-out cardigans.

Nuclear option
1. New black heavy-gauge knit dress. Deep vee neck, 3/4 sleeves, cool assymetrical buckle closing on one hip, knee-length. I've worn it only once and very great in it. It's the only dressy outfit in my whole wardrobe. If I start out dating him with this, there's no where to go but down.

Love new black top, love new black jeans, both make me feel more confident, but too much black? Blue jeans with any top too casual? Any color jeans too casual?

He's also in his 50s, an insurance agent and perhaps old-fashioned? I don't know. This is for drinks only, not dinner, so I think I can dress down a little?

This leads to another problem: I'm already super anxious about this and second-guessing myself like crazy--skittish and poised to cancel at any provocation--but one of my great worries about dating at all is I DON'T HAVE THE CLOTHES FOR IT! Nor the money at the moment. Will soon, but not for a few weeks. (Not to mention the whole dreaded underwear situation--lots of serviceable, comfy, deeply ugly and unflattering bras. 2 extremely uncomfortable, stabby "sexy" bras.)

Please help me dress for this first date, and maybe for a couple subsequent ones--if there are any? Thanks!

posted by primate moon to Clothing, Beauty, & Fashion (19 answers total)

Dress to feel confidant, to me it sounds like the black top with the blue jeans, basics are generally good anywhere - would they be appropriate at the meeting place?

Also, I've always been a fan of some effort for the first date, but no need to wow anyone until they've earned it.
posted by cestmoi15 at 3:59 PM on January 22, 2015 [2 favorites]

Black is totally fine, especially if you feel comfortable in it. Make sure you're happy with your hair, and if possible wear heels of some sort, just so you feel a tad more dressed up.

Have fun!
posted by Dragonness at 4:00 PM on January 22, 2015

I'd go with the blue jeans and the black top, and throw on a scarf or necklace for some added interest. Have fun and good luck!

(And don't even begin to worry about underwear; if and when it gets to the point where they will be making an appearance, neither of you will give a crap about what they look like.)
posted by Bretley at 4:01 PM on January 22, 2015 [4 favorites]

I think the black & black would be fine if you have some punchy, colorful shoes. Flats are fine, or heels, whatever you like. Save the dress for your first dinner date. Have fun!!!
posted by jabes at 4:02 PM on January 22, 2015

Jeans and black top. You'll look great! Have fun and enjoy the date.
posted by jennstra at 4:05 PM on January 22, 2015

Best answer: Love new black top, love new black jeans, both make me feel more confident,

Sounds like a winner! And then the knit dress for date #2. And don't worry about it beyond that. Enjoy yourself.

(Not to mention the whole dreaded underwear situation--lots of serviceable, comfy, deeply ugly and unflattering bras. 2 extremely uncomfortable, stabby "sexy" bras.)

Bras shouldn't be stabby. And they sure as hell don't have to be ugly. The single greatest thing I ever did for my confidence was going to a specialty bra store and finally getting the right size bra. When you can afford it down the road, it will be worth every penny, guaranteed. A well made bra will last a long time if properly taken care of. But I'd also like to tell you that when I was a poor, busty grad student, I found an amazing guy who loved me despite my ill-fitting, overwashed, and deeply unsexy white granny bras.
posted by futureisunwritten at 4:12 PM on January 22, 2015 [3 favorites]

I would wear the items from your first two lists that look the best together.

For one thing, no dude is really going to study the cut of your denim and use that to determine whether you're interesting or not. And anyone who would is not someone you want to go out with anyway.

For another thing, I feel like the goal on a first date, especially a somewhat casual date with someone you don't know at all, is to look like you. You want to be the most flattering version of you that you can reasonably be, but yeah, the goal here is to look like a pretty version of yourself.

I'm leaning toward the dark red top, but without seeing it with any of the pants options, I can't weigh in.

I wouldn't worry too much about "too boxy" or "too loose", since that's the trend in tops right now anyway. I mean if it actively looks bad or clashes with the rest of your clothes, maybe not, but assuming that it's flattering, again, anyone who is going to scrutinize you that hard isn't worth knowing.

I wouldn't choose the black top and black jeans for myself, but if you feel great in them and really think they work together, go for it.

I do not think jeans are too casual in this instance, and in fact I'd reserve the dress for an explicitly "nice" outing like dinner at a restaurant where jeans wouldn't be appropriate, or the theater, or something.

I'd be tempted to just wear the comfy underwear unless you really think things are going to escalate from strangers to "this person has seen my underwear" in the course of a few drinks.
posted by Sara C. at 4:22 PM on January 22, 2015 [1 favorite]

Another vote for the blue jeans and black top.
posted by serelliya at 4:24 PM on January 22, 2015

Response by poster: Just a note: no, there will be no underwear sightings for a while. That's a whole nother level of craziness and anxiety. I'm just stressing about the future as well as the here and now. Always a mistake. Oh, and my bras fit well (I get a new professional fitting every few years), it's just that the most comfortable ones are the less structured type which translates into kind of saggy for an overweight mid-50s woman. I can't wear underwires at all!

Thanks so much for all the supportive responses!
posted by primate moon at 4:34 PM on January 22, 2015 [1 favorite]

Another vote for black top with blue jeans. Maybe try for something casual and fun with hair / shoes / jewelry, just to add some interest and personality.

You'll do fine. :)
posted by jessicapierce at 4:45 PM on January 22, 2015 [1 favorite]

Best answer: Black and black. Walk up to him and say "hello, I'm Johnny Cash" in your best Cash impersonation. Black fancy dress is right out, this is a casual date.

Be comfy, have fun. Keep in mind he's probably nervous as well.
posted by vrakatar at 4:46 PM on January 22, 2015 [2 favorites]

Another black top, blue jeans, with accessories -earrings, scarf, necklace, something. Or, funky shoes.
posted by kellyblah at 4:47 PM on January 22, 2015

Best answer: I might also recommend getting a mani or pedi, not that you need it but just to feel special. Just try and have fun and be light. Just see it as an opportunity to learn about a new person, rather then trying to impress anyone, taking the focus off you will make you more relaxed about it. And, good for you for getting out there and trying something new- awesome :)
posted by sistertips at 4:48 PM on January 22, 2015 [3 favorites]

I'd wear the dress. You say you look great in it, so I'd assume you will feel confident in it. You say there'd be nowhere left to go but down, but why? Even with little money right now, surely you could find a nice skirt or two in a thrift shop?

I agree with the advice to get a salon service or two, but if you can't afford it then maybe do your own nails or something? I don't do manis because I can't have nails for my work, but I will usually get a facial and/or eyebrow wax before a first or a big date. It makes me feel more confident.

I had a first, fairly blind-ish date recently (from online) and I wore a mid-length flowy skirt, tights, and nice sweater. I can't imagine wearing jeans and a boxy top on a potential-romantic-chemistry-assessing date. :-( I'm in my early forties, but I'm sure I'd feel even *more* that way by my mid-fifties. We can't rely on the gift of easy attractiveness from mother nature that we could when we were most fertile, so why not do what we can to enhance our attractiveness?
posted by mysterious_stranger at 5:14 PM on January 22, 2015

Response by poster: Ooh, eyebrows waxed--good idea! And bra fittings are free, btw. My body is pretty boxy, so clingy, more shaped stuff isn't the most flattering. And jeans are definitely the most flattering pants on me, even if they are casual. They hold in my big, squishy belly and lengthen my short, stumpy legs.
posted by primate moon at 5:22 PM on January 22, 2015

Best answer: You've already marked best answers so maybe I'm late, but:

Wear whatever makes you feel sexy in the context of the formality of your date.

If you walk out your door feeling confident about how you look, you're going to act confident, and that's the sexiest thing of all. I'm not saying dress to get laid, unless that's what you're going for. I'm suggesting dress for what makes you go "Hey, I AM AMAZING HOT SHIT" when you look in the mirror. Not what he thinks or what I think or what they think. What you think.

Because if you think you look good, so will others, because at the end of the day--confidence is sexy as all hell. And if this specific guy doesn't? Well he's obviously an idiot and you can do better :)
posted by feckless fecal fear mongering at 6:17 PM on January 22, 2015 [6 favorites]

Black and black, but add a pretty, colorful scarf. You can buy very inexpensive ones that look really nice with rich colors.
posted by raisingsand at 6:29 PM on January 22, 2015

I am a 50s guy who went on a blind date last week. I have no recollection what she wore, but she had a great smile and was really funny. We are going out again next week. (I wore my guy uniform of a button down blue shirt and khakis.) My point is that worry more about being relaxed in a good mood than what to wear. Having said that, I would wear the black jeans with the black top.
posted by 724A at 10:18 PM on January 22, 2015 [8 favorites]

Men notice your confidence more than your clothes- wear the black top and bottoms!

I had a very funny conversation with a man I dated once and I was trying on outfits for him and he said- you girls are so amusing, we men don't care! We just know we're supposed to tell you you look nice!

It was sweet how he said it. It seems to be true as well- as long as we dont stick out as Inappropriately dressed for the occasion they don't notice much :-) now I wear the same outfits twice etc. I hope that puts your mind at rest.
posted by catspajammies at 5:57 AM on January 23, 2015