This is a purely opinion question:
What do you think looks good on male riders? Pictures and/or links are helpful.
Breeches, boots, and nothing else
Sorry, I couldn't resist. A girl's allowed to dream.
It's not about how you look. It;s about how you enjoy the ride.
If you're not showing, whatever is comfortable. I will warn you that if you ride English, jeans are not comfortable. That seam in the crotch really gets you. Breeches are very comfy English. If you don't like the look, the newer ones on the market now really do come in a lot of styles to make you feel as comfortable as possible. I'm not that familiar with Western. But in English, you will want either tall boots (expensive, and I think uncomfortable) or paddock-boots with half-chaps. This combo basically looks like a tall boots, but gives more versatility regards to fit and comfort. You have to protect your calf in English, or your calf can get caught between the stirrup-leather and the saddle-flap, which is very painful. Now there's something that can make you scream like a little girl. So guys don't wear the breeches and boots to look cool, or weird, or gay. There's a very good reason for them. Personally, I think guys in breeches and boots are hot. Jeans and cowboy boots is pretty hot too.
You should see what I wore today. Even my non-horsey, fashion-challenged husband did a double-take: I have riding tights with an odd purple inset at the thigh (they were closeouts - but oh-so-comfy), then I have a tie-dye purple-and khaki top (also very comfy, and it's SFP), and my purple Kerrits cap with little stampeding horses on it to hide my helmet-hair. Coupled with my tall boots, I'm not sure I'm fit to pump gas in this gettup. But it sure is comfy, I had a superb ride, and the horse really didn't seem to care one bit. I can tell you that cantering through the woods, on a steep, rocky trail, feeling the wind and mane whipping in my face - I truly don't care what I look like - 'cause it feels GOOD!
Am I the only person here who would love to have a beer with BSMS sometime? I have blown so may drinks through my nose reading those posts! Thanks for the laughs.