I tried on the pants but the drawstring just won't cut it. It has one of those plastic, spring loaded cinch do-dads. It felt too loose and that was just in the dressing room. To bad since the price is reasonable.
I have a pair of these and will have to look at the waistband. No problems when riding with them. Nothing moves around unexpectedly.
For hands, I have been told my many that the bar mits are the way to go. Seems like regular gloves or just thin liners inside of them are enough. I've not tried them -- frankly, commuting both ways in the dark gets old quickly, so I don't know if I will.
I have lobster gloves and my hands sweat enough that they get wet and cold. I make it about an hour of my commute and then have problems.
For the helmet, I was thinking if you stay in a fancy hotel, grab a shower hair cover. Try it. Then you know if such a thing will work for you and can get something specific.