It is fairly simple as a guy to dress for work, but it is not so easy for social functions. How does one avoid douchebaggery in dressing while still giving the appearance of a man with style?
Originally Posted by Meerschaum
I'm with Nina on this issue, and a lot of it is based on my region (East coast), job, age and background, but it starts with my approach to a session. To me a visit with a sporting lady is an event and I treat it as such and that includes how I dress. It also has to do with respect for the lady. I expect the lady to be well "undressed" with nice make up and hair, so for me to show up in shorts and a t-shirt seems a bit disrespectful.
The OP says it's easy to dress for work, so maybe he should start there. I still have to dress for work for out of the office events, which are many, so I am comfortable in a suit, still "invest" in good suits and look good in suits. I also know that a lot of women like men in good suits, and one grand dame of our local hobby scene says that she is strangely turned on by French cuffs, so I will wear French cuffs in the hopes that others share her quirky fetish. Still, the basic idea is to present the message that "our" time together and "you" are important to me.
Another advantage is that you look like you belong in a nicer hotel when you're wearing that power suit, so no one hassles or questions you.
On the occasions when I don't wear a suit I still try to project that this an event. This summer I went to Nordstrom's and bought some nice dress jeans and collared shirts which I wore with Italian loafers (no cowboy boots). The look may not be true GQ and more like suburban dude on a date, but it imparts the message that I care about the session.
You clothes can also be a conversation point. I also bought (on sale) a pink button down shirt from an old line clothier and paired (that's a fashion verb) with those fancy jeans and a blue blazer. When I went to see my date, a wonderful Brazilian girl, she laughed and said a lot Brazilian men would think that a pink shirt was gay, but she wasn't worried about me. I told her it was brand new and I wore it just for her. I don't know what impact it had but she and I had a marvelous time together.
I have a morning date scheduled later this week in a nice hotel in Philadelphia. I'll be wearing a dark blue chalk striped suit with a French cuffed shirt and silk tie. My black cap toed shoes will be highly polished. I'll bring nice pastries, coffee and fruit. I'll have the donation in a funny card and all of this is to project the message that I appreciate that she is going to share something special with me. If this makes the lady happy, relaxed and comfortable then good things will come my way.
Still you have to be flexible. If the lady is camped out at a mid level chain hotel near the airport I will be more casual because the suit will stick out. If you don't wear suits it would be silly to buy one just to hobby. And much of this is regional. Jaci's dream boat cowboy look, which projects the "I care message" in Texas, would be seen as affected in my hood.
I use to see a girl in Texas. She said Tommy Bahama was for old guys, so I don't buy that brand. She said she was going to take me shopping at Diesel. I'm not sure what Diesel is but I ain't ever going there.
. But, even here, you don't see much denim at the opera. 
Hahahahaha that was a good catch!!!!!! I laughed so hard when you mentioned this, at first I did not even notice.... Bwahahahahaha. By the way, the guy is the main actor for "White Collar" , hot man, and I was googling his dress code, because I liked it. 
