Jeans in, unless it's muddy! I think it looks kinda stupid when they're out, unless they were made for it like what PDJ was wearing. There was a lady at my old barn that had some real tall Tony Lamas, not sure she could tuck them in if she wanted to! She said she'd wear them at the barn, but nowhere else...and I agree. Wearing them like that outside the barn kinda screams "hey, look at me! I ride horses!", like the type that wear spurs to anywhere but the barn...lame!