Dressing very casually for a date

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I always dress very casually. When it’s hot, I wear a t-shirt, jeans and sneakers. I have large tattoos on my arms that are very visible, if that matters. When it’s cold, I wear a hoodie, jeans and sneakers. I have nicer clothes in my closet, but I hate dressing nice because it’s extremely uncomfortable and it’s just not my style. I’m in my late 20s, but I look no older than 18 and I’m tall and skinny.

If I date girls in their late 20s and early 30s, is it okay to dress that casually on a date? Is it considered weird for a guy in his late 20s to wear those clothes during a date? I’m primarily interested in doing a coffee date for a first date and then dinner dates after that, but not at expensive restaurants.

Is it okay to wear those clothes on a coffee date if it’s the first date? What if it’s a second date and it’s a dinner date at a relatively cheap restaurant ($10-15 entrees)?

What do guys usually wear on the first few dates if they are coffee and dinner dates?

Is it a deal breaker if a guy dresses very casually on the first few dates (t-shirts and hoodies etc.) if they’re coffee dates and dinner dates at restaurants that aren’t very expensive? What do girls in their late 20s and early 30s usually think of a guy that dresses very casually for a date? Is it a bad idea to have tattoos showing on your arms (if they’re large tattoos) during a coffee or dinner date?

Do girls usually dress nicely for a coffee date? What about a dinner date?

Why not wear a polo shirt and chinos?

I don't see anything wrong with jeans and a t-shirt. Personally, I'd prefer that to a polo shirt and chinos, but that's just me.

Edited to add: Tattoos are not unusual these days - very common where I live, and women have them too, so I don't see that that's a problem.

I said chinos and a polo shirt because they comfortable, and most people do not feel it is too informal for a date.

There are people who find jeans and a tee-shirt too informal, especially on first dates.

Me too.

I'm a very casual dresser myself. I'm no clothes hound. I forget whatever designer (or whether there is a "designer") is on my clothes, usually

I'm talking about first dates. I just believe polo shirts and chinos are the perfect compromise between formal and informal. It's unfortunate that we have to play the "courtship" game. But, sometimes, you have to play it.

Just like on job interviews....one cannot show up at a job interview with jeans and a tee-shirt. Chinos and polo shirts are actually at least somewhat risky in some industries. When I started working in the late 1970s, people had to wear suits to interviews even if they were interviewing to be something like a file clerk.

Snazzy jeans and a cool tee are acceptable for a really casual coffee date. Beyond that, there's an expectation to dress up a bit more... but you do not HAVE to.

If it makes you uncomfortable to be dressy, why date a girl who wants/likes dressy? Why not date a girl who is cool with undressy - surely there are lots of them out there!

Sounds fine to me. I don't dress up for my dates, I wear what I want. But I try to dress appropriately for the venue. And I would hope my date would have the same approach. I met a guy at a restaurant once and he wore a singlet. No problem at all if we met somewhere more casual, but I felt it was a bit inappropriate to dress like that at a place like that (simply because it seems to be social etiquette for males not to wear singlets in restaurants). I'd have felt the same about it if it was a friend, so I don't attach any particular dress codes to dates specifically.

It depends on your idea of casual. I would go with a tailcoat, blazer or double breasted jacket with a nice pair of oxford or monk strap shoes.

Never ever go to a date wearing a track suit, military attire or cargo bottoms. If by casual, you are referring to knitwear or a shirt with jeans and shoes, that is fine depending on the setting, atmosphere and the expected attire.

There's a difference between casual having made an effort and casual as in "I don't care enough about you to have made the least effort to impress." Only you know where you fit. If you know you look a bit young, there are few steps you can take to look 'more your age'.

No hoodies. Bad form for a date. Unless your date is involving jogging or mugging.

You can still dress up a little and be really comfortable. Jeans, plus button down over t-shirt, good quality belt and nice (but comfortable shoes). It may take you a while to find the right shoes, but for me that is critical. It is absolutely worth the investment in time and money. Athletic shoes are for athletics.

Personally I love the rugby shirt (a good heavy weight rugby shirt is hard to beat), if it's cold you can wear a t-shirt under jeans and casual leather shoe look. To be honest, I love the rugby shirt on men who play rugby, but that's neither here nor there - even men who don't play rugby look good in them.

This esquire article does have some good tips on dressing casually: http://www.esquire.com/style/mens-fashion/advice/a4199/casual-clothes-for-men/

I think T-shirt and jeans are fine for a coffee date of inexpensive place. Just stay away from any offensive designs and wear good jeans, clean and in good shape. Offensive t-shirts and torn, faded jeans are not a good choice.

I don't understand this dressing up thing. I think it is important to just be yourself, you'll be more comfortable. Having to dress up to go on a date feels so superficial to me and I've never done it. I like to be myself and upfront with things from the start as I have enough confidence in who I am.