How to Dress for Coffee Dates?

[Bboy100]

I'm one of those guys who likes to dress nice (relative to those around me). Not only because it's impressionable to women, but also because I genuinely enjoy looking good. I live in a very liberal part of the country where there is literally no emphasis on dressing well. There are almost NO guys who dress well. A lot of dudes literally walk into bars/clubs with gym shorts and a sweatshirt on.

Right now, I wear:

Short hair styled into a "messy" look.
A silver necklace
A Silver Seiko Watch.
A button down dress shirt or a V-neck shirt.
A nice black leather belt.
Dark designer jeans
Leather dress shoes
A Puma & Ferrari biker jacket made of real leather.

It's pretty much always cold out where I live.

I feel like when I go out to bars/clubs, it's appropriate to dress the way I do. However, I have to take some of the girls I go out with to coffee dates cause a lot of them are under 21. Given that it's day time and not a bar/club environment, and there isn't a culture of having good fashion here, I fear that I might come off as tryhard to a girl who doesn't know me. When going for coffee, should I adjust to a more "casual" look? Or is it ok to stick out from the crowd/look overdressed?

 

[Troy]

Bboy,

Rule of mine is watch how the people in my environment dress and go dress slightly better. You don't want to be the ONLY guy dressed EXTREMELY GOOD around lousy dressed guys. It's the equivalent of dressing in a tie and jacket with designer dress pants and pointed shoes in the gym when you are going to workout. Yet every other guy is in shorts and a tee shirt and sneakers. As silly as it sounds lol

I won't tell you how to dress, just keep that rule in mind wherever you go. Girls need to know you are somewhat apart of the crowd yet their is something that makes you a little bit different in a good way. See the thing with fashion is it changes. You wearing a jacket and designer jeans wouldn't fit it if you were in a ghetto full of Rap cultured people. But your style would fit in well with my Caribbean country people in December.

A next thing is you don't want guys feeling they can't relate to you ( some may even dislike you only because you= fashion) is so Different it's mind boggling. If you dress slightly better than those guys while still looking neat you will be at a advantage in making girls blush and making guys wish they were you

Troy

 

[ray_zorse]

I think it might be a good idea to swap out the dress shoes for some Chelsea boots (and keep the dress shoes for nighttime), but otherwise I'd say you're as good as gold. The dress shirt could maybe be replaced with a tight muscle tee shirt but I don't think so, I think the dress shirt helps to guard against grunginess. You could however consider a shirt with a bit of trim on it (like I have this white shirt with some black detailing) which would give you a slightly more casual look.
Ray

 

[Cassy]

Always be the best dressed guy in the room. Its much better to be overdressed than to be under dressed. Casual doesnt mean looking like everyone, you can dress casual and still be the dressed man in the room. Pay attention to details, learn how to match colors of the clothes you wear. Girls wont think you're trying to much when you over dressed, they like a man who knows how to look good. Plus if you know how to dress well, they'll always be happy to introduce to their friends and take pictures with you

 

[Bboy100]

Thanks for the input guys! Yeah, I figured I'm probably doing ok. I just wanted to make sure.

I think it might be a good idea to swap out the dress shoes for some Chelsea boots

Yep. My footwear was actually my main concern. Boots seem like a good alternative which I hadn't considered. I'll definitely invest in a pair.

 

[mb1]

Sounds like a solid outfit! Bit of a different perspective, but perhaps instead of dressing for her, consider where you're coming from or going after on a daily basis. Got a meeting or presentation later? Wear a blazer and brush it off. Coming from the gym? Maybe some wet hair and fresh tee under a varsity jacket.

Most leather (or suede) shoes or boots should do, so long as they're not closed lacing (which are suited for suits). http://www.oliverwicks.com/article/shoes

A GC convention would have lots of Chelsea boots haha. They go well with that bad boy look (black, especially), though maybe you should be taking her to a wine bar or tiny restaurant with tablecloths just for a cocktail, after which a cheaper meal can be cooked up back at your apartment Another spot for early in the day is ethnic markets (like Italian or Chinese for tea), or at worst coffee shops closer to areas where adults conduct business. Then you can get away with dressing up a little more to those surroundings away from the jarring contrast of students in hoodies cramming for exams at Starbucks, etc.