I tend to dress the same regardless of where I'm going. In summer, cargo shorts, an athletic shirt of some kind, and lite hiking boots. IWB holster carries my XDs. In spring, fall, and winter, it's jeans, a tee-shirt, with some sort of zip up top, and a pair of Danner hiking boots. During those months I carry an HK30SK OWB but under the zip up top. I wear these same clothes to dinner, to work, on the weekends, out for a hike, riding my bike, or whatever really. There is nowhere in my state where jeans are unacceptable, and in my line of work, what I described is considered business casual.
The one piece of obvious give away clothing I wear is I will typically have on a Ruger, S&W, or HK hat, if I'm not shaved bald at the time. Folks who know, nod and say nice hat. Folks who don't know ask me, "What's HK?" The former, I don't mind if they know. The later, I explain, and if they are uncomfortable with me being a gun enthusiast, I couldn't care less. I'm a legal permit holder. Go ahead, be scared and shocked if you want. I don't care.
Whatever happened to wearing a sport jacket or suit? It's common practice here and conceals a sidearm very well.
If you dress like that around here everyone says "I'm sorry, who passed away?" I don't "attend" a traditional church, or any church for that matter. But I do run the sound board at my girlfriend's spiritual center, and when I'm there, I dress the same way I described above.
The tactical dressing gang does seem a little uniformed. My favorite is when I see a guy wearing a tee-shirt and a long sleeve button up plaid shirt over it when it's 100 degrees. I look for the tell tale grip printing and more often than not, it's there. But what do I care? I assume they are legal, and if not, I'll find out soon enough.
I guess I dress in what I find comfortable, and how I want. When selecting clothing I do consider if it is good for concealment and if I can get a gun IWB. It seems silly to me for people to have special outfits for carrying. Shouldn't that just be your every day attire? And if it is, and it's obvious they are carrying, what's the difference?