Physically, you want to be comfortable. That means lighter clothes in warm weather, thicker layers in cold, and a good fit all the time. Changing your wardrobe seasonally adds a little expense when you’re first building it, but over time you’ll end up saving wear and tear (and sweat damage) as you spread your usage out over more weather-appropriate options.
Socially, you want to look respectable at all times, without inviting trouble. And yes — wearing an expensive business suit to a dive bar in a bad part of town is inviting trouble!
Make the effort to fit in while looking sharp. That means jeans and even T-shirts, when jeans and T-shirts are appropriate. Just make sure they’re nice jeans and T-shirts: well-fitted, in good repair, and flattering to your body.
If you’re always wearing the same basic outfit, rethink your strategy. Odds are you need a little variation, in one direction or the other