Anonymous wrote:

Anonymous wrote:

I'd rather be dressed completely generically and let her shine than be the focus myself.

Well, between being the focus yourself and looking like her servant, there has to be a point where you can look like you compliment each other.

But why does that matter?

Why does it matter to look decent at work? What do you signal to the outside world?

Make sure to show some nice cleavage

Khakis and a button down.

Anonymous wrote:

I'd rather be dressed completely generically and let her shine than be the focus myself.

Well, between being the focus yourself and looking like her servant, there has to be a point where you can look like you compliment each other.

But why does that matter?

I'd rather be dressed completely generically and let her shine than be the focus myself.

Well, between being the focus yourself and looking like her servant, there has to be a point where you can look like you compliment each other.

Anonymous wrote:

When I was younger, I was into clothes and fashion, but I learned through time it wasn't worth the time and effort.

What exactly takes so much time and effort, since you are a guy?

I probably should have added "expense" but I would include: looking for and buying new clothes; keeping shirts and pants pressed and neat; polishing shoes. The reality I have found is that, as a guy, that is largely wasted time and effort. I think it is important to maintain a bare level of presentability, but beyond that there are minimal returns. My time and effort is better spent doing other stuff so my gf/fiancée has the time and effort to look her best. All the other guys and gals are going to pay attention to her anyways. I'd rather be dressed completely generically and let her shine than be the focus myself.

When I was younger, I was into clothes and fashion, but I learned through time it wasn't worth the time and effort.

What exactly takes so much time and effort, since you are a guy?

My husband wore nice jeans and a beautiful white/blue seersucker shirt. He's pretty tall and he had a tan so the look rocked.

I'm recently engaged. Before I met my fiancée, I went on lots of first dates with women whom I met through apps. I, generally, didn't treat first dates as anything special, clothes-wise. I usually wore whatever I had been wearing for the preceding activity. If I came from work, I wore work clothes. If I was coming from the gym, I would bring a change of clothes, consisting of a nice pair of jeans and a nice shirt. As a guy, I never thought that I had to dress too well, just sufficiently presentable. (When I was younger, I was into clothes and fashion, but I learned through time it wasn't worth the time and effort.)

Anonymous wrote:

Anonymous wrote:Except the boats hoes, I would go with nicer shoes. Oh and the colors in the picture
are funny, jeans should be normal jean color and the shirt color something that make you look good and smart..

Should he tuck in his shirt? Or am I just getting old and channeling my dad?

Leave it out. Project “relaxed”.

I'm struggling with this too because I lost 60 pounds and what I had doesn't fit but I don't know what to actually get to wear on dates. I had a fat girl style. It doesn't work for my smaller body

Anonymous wrote:Except the boats hoes, I would go with nicer shoes. Oh and the colors in the picture
are funny, jeans should be normal jean color and the shirt color something that make you look good and smart..

Should he tuck in his shirt? Or am I just getting old and channeling my dad?

Anonymous wrote:polished shoes and coordinating socks, nicer pants or jeans, button up shirt of some kind.

I love a button up shirt with jeans. Nice. Polos can get saggy and sad looking.

Anonymous wrote:Condom?

Probably don't need to wear the condom to the bar. But I'd say keep one or three handy just in case you want to put one on later.

Anonymous wrote:Jeans, nice loafers, some sort of stylish but not over the top socks and a well cut polo (i.e. not one that has really long or wide sleeves, please see: http://classicamericanstyle.net/wp-content/uploads/2016/08/IMG_4219.jpg).

Ugh. No.

Well fitting jeans or Bonobos-type pants. A button down shirt with a pattern (like polka dots, etc). No loafers, boat shoes, or Crocs.