It's a toughie and to be honest the best bet is padded stuff under regular baggies as Kies says you will either lose weight or you won't cycle enough to be worth all the new supersize kit.
Once the weight is down a bit there's a lot more selection but most of it is pricey, Swrve, Rapha, etc and they all seem to like their 'trim' fit cuts these days. If you're not going too far or your day will be pootling on and off the bike then you can get boxers with varying degree of padding. I've tried 3 or 4 types but found the Rapha ones the best by far. Then you can just wear whatever shorts or trousers take your fancy, I tend to avoid jeans but combat(minus the camouflage) are ok.
For longer/harder/training rides then my kit of choice while heavy is bib shorts with a base layer underneath(protects against nipple rub), cheap baggy shorts or longs(think Peacocks/TK Max here), a cheap micro fleece with a dropped back(
Millets do some good ones) and if it's needed a wind/waterproof outer layer on the top. As the weight comes down the lower baggies can go but I use micro fleeces or cheapo cycling tops for any training rides.
