Dressing for a first date (men's clothing)

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Here's the deal. Long story short, I'm literally just exiting a 12 year relationship. We barely ever went out. Especially over the last few years. Now, I'm talking to this girl whom I am getting into and we will be meeting probably next weekend to go out. Probably dinner, maybe some drinks. Nothing too crazy.

My question to you guys is, how the hell is a guy supposed to dress for something like this? I REALLY suck at dressing myself, and even though I've been in 3 long term relationships never once had a "first date" in it's traditional sense. So I am totally clueless here. I need to buy new stuff for sure, so Im gonna need some help with it.

Please, be specific. Provide pictures if possible. I'd prefer only women and men who are experienced daters answer this one please. Thanks alot guys.

You can't go wrong with a polo shirt and Dockers-type pants. And either loafers or comfortable dress shoes.

White pants would be great, with a colorful shirt. This is summer, after all. And white loafer-type shoes.

Wow, ok. Polo shirt/khakis was sort of my idea to start with. So... I guess that's good. White loafers, huh? Geez... If I gotta

What's the dress level? And how do you dress normally. Maybe it's my age, but if I went out to an average restaurant with a guy I'd just expect him to dress like he normally but, but maybe slightly nicer? So like jeans and a t shirt that aren't beat up at all. I don't know about shoes because I don't notice most men's shoes. Something plain and not flashy though. If you're going on a date don't wear you're bright red athletic shoes unless it goes with your outfit .

I'm not really into like... dressing up and people dressing differently than they're comfortable with. It just seems weird. I like to wear dresses on dates, but I also already own dresses and wear them a lot. So seeing me in a dress and flats wouldn't be weird or out of character.

Then again I assume you're a bit older if you've been in a relationship for 12 years and I don't know how older people dress for dates. Other than other women.

Kraftiekortie I think is right at least from what I've seen of my friend's mother's boyfriend. He usually wears khakis and a polo when they're going out.

Well age wise, I'm probably (not sure your age) split right between you and Kortie-- I'm just about 38. My mentality is certainly younger than that, and the girl I would potentially be dating I believe is 31.

Normally I dress terribly. Like I just got out of bed. I wear sweatpants or basketball shorts probably about 95% of the time. The other is usually some kind of khaki or cargo/work type pant. And I wear either solid colored t-shirts or band tshirts just about always. And regular sneakers. And almost always a baseball hat, which I'd naturally ditch if we went anywhere decent at all. Or maybe altogether.

I guess the only other time I had a 'first date' was the first time I my my ex-wife. It wasn't really much of a date. In retrospect, it was a pretty fitting symbol for many reasons. Our first date, I drove to her moms house and hung out with her in her bedroom, no sex that time tho. But I have a point-- I was so worried about how I should look. So I show up, looking pretty decent, nothing outlandish at all. A low key sweater, some jeans. But it was totally not how I normally looked or presented myself. Turns out over the years when we reflected on that, she never could understand why I showed up like that, because she would have had an even better impression had I showed up how I normally looked, as that was a look she found attractive, not how I showed up so much.

I'm really just a fish out of water on this one. Because there's no conceivable way I should show up how I normally look. So I sort of HAVE to do something different. And maybe consider some overall across the board changes since I'm going to be single. I go to work the same way I described, so I don't even have that to go off of.

You didn't tell us anything about the girl except that maybe she drinks? Usually you want to match what she wears in terms of formality or casualness.

Last edited by BTDT on 12 Jul 2016, 8:31 pm, edited 1 time in total.

No sweatshirts or sweatpants.

The rest is personal opinion

Jeans are always a good casual option along with polo shirts, most t shirts, and checkled shirts.

For a more smart evening date chinos or smart trousers with a shirt is sensible. Wearing a plain top underneath will make it more comfy if your sensitive to shirt material like me.

Mostly just make sure you feel good and feel like you look good in what your wearing .

I forgot to add that wth the checkered shirts it looks cool if they are open and you have a pin t shirt or band shirt uderneath

I did mention she is 31. She seems like a pretty down the middle, normal kind of person like myself. No evident outstanding sense of unique style or some sub-cultural affiliation. I've met this girl via internet and texting, so it's hard to fully gauge much more than that just yet.

No, not the white loafers.....and khakis? How about a t-shirt and some denim shorts or cargo style shorts that aren't that awful khaki color and brown or black loafers. Unless the woman you're going on a date with is a yuppie then yeah polo shirt/khakis(make sure they are the awful khaki color) with white loafer shoes would be best.

Do you really think that she might not accept to go for a second date just because she doesn't perfectly like what you wear on first date?

And you didn't say anything about your body type- which is important.

If it's a casual place, I usually just wear jeans and either a collared or button-up shirt. Nothing too special.

I wouldn't wear a t-shirt for a first date.

Jeans and a button-down/polo shirt are okay, as long as the jeans don't have too many holes in them.

Nice sneakers are okay, too, instead of the loafers and all that.

A t shirt with an open button down is cool aswell.

My attitude to these things is that if you really hate what I normally wear then the relationship isn't going to work anyway, cos I'm not going to change how I dress for a woman.

If it was a nice restaurant I'd probably pick by better\smarter jeans and throw on a smartish shirt but that's about all. I know first impressions and all, but you don't want to set wrong expectations either. It will be important to her to know that if you do go somewhere smart that you recognise to dress yourself a little better than normal, but it's also important to let her know that isn't your usual style. I'd maybe bring it up as a conversation piece, "You look nice, do you normally dress like that, or more casual? I like to dress up for a nice restaurant but I normally prefer to wear <describe your usual style here>".

Basically, before making any diagnosis, I need to see what you look like. So picture plz *cute smile*.