When it comes to clothing, I have many styles that may coincide with the changing weather.
I live in Texas and it can be incredibly cold in the morning, warm in the afternoon and freezing at night, or any other variations. You get used to it.
Personally, I like to dress for occasions though. If for instance say I'm going to a bar with friends, I can wear jeans and a t-shirt. If going on a date, why not wear slacks and a button shirt or polo. If going on a high-stakes date (such as a fancy restaurant, out on the town, or a club) I will lean more toward shirts and ties with jeans and boots.
A good friend once told me, never dress to impress anyone but yourself.