Depends on the cup, if you have a jock strap or compression short... I'd suggest undies or compression shorts, jockstrap/cup, then fight shorts. Or just get the Shock Doctor compression shorts with flexcup and just wear them.
I like to put my Gi on first, then (and only then) I put the jockstrap on over the GI. This will show all the rest of the guys at class that you are someone to be reckoned with. Oh...and always wear a pink cup.
The Shock Dr cups are grey with a carbon Fiber looking trim and a little bit of orange, I'll post a piture in a little while. The best looking cup made. I looks like a part out of a exotic car, lol.
Does anyone know where I can get hold of a steel cup? Either shops in the UK or online stores... thanks. I've been looking for a while but yet to have any luck.
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