Here is the first installment of "Goon Eye for the Boot Guy". This is an intro to Combat Casual. First step, throw away you Gruntstyle, or other Motard shirts... Do it. This is the way.
Comfort is key. There are numerous companies who make short sleeve button ups for hiking. They work. Get one that is cut for your body type. Don't try to get a form fitting shirt if it looks like you retired last week.(JFC how do some of you get fat so fast?!)
Brands can vary, along with price points. You can go expensive with some Patagonia, or save some money with some REI COOP. Have some fun and get some wicked prints. I hear Aloha shirts are all the rage these days...
Do the same with t-shirts. Get something that is a blend, so when things get hot, your nipples don't bleed. Solid colors are always a plus. Don't forget the tank top. Be sure to grab a few of these. Suns out Guns Out.
Time to move on to pants. So many options. You can go all the way from some 5.11(form fit ones, not the boxy looking ones) to your regular hiking pants from brands such as Patagonia, prAna, Kuhl, and Northface. Even Eddie Bower has some comfortable ones.
Just make sure they fit properly, and are a blended material that will let your boys breath, while not ripping while putting hate down range.
For shorts, DO NOT WEAR GAHDAMN CARGO SHORTS! I say again, DO NOT WEAR GAHDAMN CARGO SHORTS! I am a big fan of @Chubbies and switch between 5.5" and 7" inseam. Skies Out Thighs Out. They also stretch, so in the belt carry is simple.
Be sure to always have Ranger Panties on. I tend to drink in excess, so if I decide to go streaking to the quad, at least I technically have shorts on...
Belts, these are user preference. @Snakeeater36 covered kit belts, but I have a leather belt I always wear for my pants. Make sure it won't stretch out over time, so get quality.
Shoes. So many options. I personally use Merrells but so many hiking shoes will work. For around town, I have regular tennis shoes. ie. New Balance(non velcro) Sperry
Jackets. You have to get a lightweight black down jacket. Can be Patagonia, Northface, Arcteryx, or REI. If you don't have one of these, people won't know how cool you are.
Watches. Get yourself an overly expensive Suunto watch, so FIS can spot you in a crowd right away. I personally have the Garmin Instinct Tactical because you can put it in Stealth mode, or as I call it, poor people watch mode.
Hats. Get yourself a low crown fitted baseball cap with your favorite team on it. After time it will fade, and carry so many memories. Low crown trucker hats work too. Wearing team hats is ok too. How else will people be able to thank you for your service.
Hair. You must have flow. If you don't have hair, sucks to be you. Maybe get a weave. For the boys that do, work on that perfect part. You want to have the front slightly pomp up before it goes back and to the side. I personally use Prospectors Iron Ore. Stays in place.
If you made it this far down this thread, know that this is tongue in cheek. Wear what ever the fuck you want. Hope you enjoyed my fashion advice. Stay Frosty, Stay Safe, Stay Sexy.
I forgot facial hair. Damn it. If you can, grow a beautiful beard. I unfortunately can not do this. My team Sargent made me shave because he said I looked like a chai boy. Don't want that...