SO not a dumb question!!! in fact, the only dumb questions are those not asked
i have a similar problem as you. finding things that fit me right is nearly impossible for me!!!
for shirts to fit right around my stomach fat (ya know, not showing off the rolls by wearing something tight on the tummy!) the top part over my breasts is way too big! (i'm only a C cup, but the shirts i used to buy that weren't so tight on my tummy were made for much larger busts!)
jeans/pants are another problem. my hips and thighs just don't match. in order to find jeans that i can get over my thighs, they're a little big on my hips.
i've been fighting with this problem ever since i can remember!! but i've finally found some clothing that fits better. i usually try to get wide leg jeans and pants so they fit better on my thighs, but aren't so baggy on the hips. and i try to get a lot of princess or baby doll type tops that fit nicely on the chest and are a little looser on the tummy.
finding the right clothes for your body is all trial and error. next time you go clothes shopping, pick out a few items you like, and then also pick out a few that you think would fit your body type better...then spend 20 mins in the changing room trying them all on. take pics if you'd like, so that you can get a better look at them, at home. see which items of clothing you tried on fit best and which types you just didnt like the way they looked at all. then just buy the items that you think fit your body the best.