As you can probably imagine, the computer game development community (where I worked for 10+ years) isn't exactly the height of fashion. To this day I still dress like a game developer much of the time because it's what I'm used to. Today I'm wearing jeans and an old Game Developer's Conference faculty t-shirt.
When I joined Toastmasters and the NSA and started doing more public speaking, I bought some nicer clothes. A local speaker friend helped me with some advice on suits and such. Dressing up felt uncomfortable at first, but I got used to it, and eventually it felt good to me.
I noticed that if I ran errands while wearing my speaking clothes, people responded to me very differently. Women would openly flirt with me. Even if I was just buying groceries, the checkout girl would be extra friendly.
However, dressing up in a suit all the time isn't me. It's too formal. But right now I don't have much between casual game developer clothes (jeans and T-shirts) and suits I use for speaking engagements or other formal events. I do have some in-between clothes, but most of them feel off to me.
I'd like to create a wardrobe where my clothes support all the ways I'd like to express myself. If I'm just working at home, I'm happy to wear jeans and a t-shirt. If I'm doing a speech, I like wearing a suit. But there's a lot of in-between ground I don't have covered yet... like if I'm going to a party or hanging out with friends on the Vegas Strip. In those situations, it often feels like the clothes I'm wearing don't reflect how I feel.