I am a lot like you; older and particular about the clothes I wear and the “look” I want with my wardrobe.
Additional issues; I am a “shirt tucked-in” type of dresser most of the time. AND I live in PA which means highly variable climate and weather conditions; 100 degree highs in the summer (along with 80% humidity) and 0 degree lows in the winter.
Guess what?
I made a few changes.
Had to.
It’s unavoidable, especially for me because I need to carry without printing because effective concealment is just mandatory in my work environment.
For me, all of the above meant that I need two concealment weapons (and both need to be small) and several holster choices for each in order to effectively conceal under the wide range of conditions I need to deal with.
So, the “trick” is to make wardrobe changes that you can live with and/or “get comfortable” with. Some things are easy and represent no real change at all. For example, because IWB works very well for me, I buy jeans with one more inch in the waist. Jeans are not a problem because they are made in different styles and cuts. You can easily find jeans that still look trim and not baggy, but that are just a bit larger in the waist. I have bought some different trousers. For me, this was a big deal. I like jeans and have worn them all my life. But now I usually wear Carhartts to work because they have roomier pockets that work well with a pocket pistol/holster combination. I still don’t like them especially, but ya gotta make SOME concessions.
I have bought several cardigan sweaters. Cardigans make GREAT concealment accessories, because you can open them instead of taking them off when you get too warm. I always hated cardigans; I am a crew neck guy. I have always associated cardigans with “geeks” and “old men”. Well guess what? I may not like the idea of it, but I AM an old man now. A lightweight cardigan works very well with an IWB and a heavy cardigan works perfectly with a shoulder rig. (A handgun behind a heavy cardigan can be accessed if you leave a couple of the middle buttons unbuttoned. And a heavy cardigan CAN be “cool”….check out Steve McQueen in “Bullitt” with his heavy weight, dark maroon cardigan).
I have also “discovered” Hawaiian and Guayabera shirts (two MORE styles I have NEVER worn before).
For me, carrying concealed has involved a lot of thought, some “attitude adjustments” and there has definitely been expense involved in making wardrobe adjustments. But I am a good ccw artist at this point; I’m comfortable with my appearance, and proud of what I have been able to figure out.
Lastly, none of your clothing is worth anything if you cannot access and draw your weapon. It is important to check all your ideas out on the firing line and to practice with it all.