It's not just overweight that's the problem. I'm normally a bit overweight. This is offset by being somewhat stronger than average in build - a t-shirt that fits snuggle around my chest but falls quite wide around the waist will hide a lot of my excess weight. But these are generally pretty hard to find.
The bigger problem is trousers - generally it doesn't matter how fit I am, the size of my thighs (muscle again, played rugby from a young age) will stop any trousers from fitting me properly. Anything that fits around the thighs is guaranteed to be several inches too big around the waist (no, a belt doesn't solve this all the time: ruins cut and comfort).
The problem is as much with the attitudes & economics of high street fashion as it is with you. I don't get as frustrated and depressed shopping when I'm in better shape physically but it's still a very unpleasant experience - and that's without even thinking about style.
Most people say "go tailored" with all the obvious expense and silliness of asking for tailored jeans etc. Buying and adjusting is more realistic if you or someone you know can sew or wants to learn (or maybe affordable professionally). But again, sadly, many high street clothes don't have sufficient build quality or extra material (at least one tailor refused me on that basis).
Always seemed to me that there is a business opportunity for providing web-ordered clothes. If the fittings were better than a single number, and were consistent, it would be a great service from the consumer point of view. Perhaps difficult to get started from the business one though, before the volume is large enough/process easy enough?
Welcome to being a woman. Remember how the old ideal figure for a woman was a small waist and big hips? It turns out that being shaped that way means shopping for jeans is impossible--unless you want them to be skin-tight on your thighs and rear and so big on your waist that your underwear shows when you bend over. My hips are 37 inches. My waist is...well, Lucky jeans made for a 25 inch waist (their smallest size) are about an inch too big on my waist (and barely possible to pull up over my rear). I have a friend with a 30 inch waist and 44 inch hips. I have no idea how she finds anything that fits her.
My solution is to always wear skirts. I wear long skirts year round. In the winter, I wear leggings under them (stretchy!) for warmth. Maybe you could get a Utilikilt?
Really, though, I suggest you learn to sew. I've been sewing since I was 3 or so. If a toddler can do it, you can do it! I've started taking in my shirts that are too baggy so that they fit my waist properly.
ETA: I have noticed that yoga pants, because of their sheen + stretchiness, can pretend to be slacks for women! One lady I know has pinstriped yoga pants. Looking at her, you'd never know she was wearing comfy pants, not proper slacks.
Same problem. 30 inch waist, but my thighs are bursting out of 30 inch pants. I typically buy 32 inch and have them taken in for $6 at the dry cleaner.
Unfortunately most conventional stores don't stock any sizes large enough. The three sizes on the rack is what you get, and if you move to a country with an average size smaller than you (or like something in a shop that treats male fashion consumers as rake-thin models just like the females), you're basically out of luck nearly 100% of the time.
I generally don't find anything larger than 36" waist where I am and that's already got room to spare at the actual waist. Of course leg length is also an issue - anything bigger than 34/36 and you must have 2m legs, right? And then adjustment prices are high too :S
The bigger problem is trousers - generally it doesn't matter how fit I am, the size of my thighs (muscle again, played rugby from a young age) will stop any trousers from fitting me properly. Anything that fits around the thighs is guaranteed to be several inches too big around the waist (no, a belt doesn't solve this all the time: ruins cut and comfort).
The problem is as much with the attitudes & economics of high street fashion as it is with you. I don't get as frustrated and depressed shopping when I'm in better shape physically but it's still a very unpleasant experience - and that's without even thinking about style.
Most people say "go tailored" with all the obvious expense and silliness of asking for tailored jeans etc. Buying and adjusting is more realistic if you or someone you know can sew or wants to learn (or maybe affordable professionally). But again, sadly, many high street clothes don't have sufficient build quality or extra material (at least one tailor refused me on that basis).
Always seemed to me that there is a business opportunity for providing web-ordered clothes. If the fittings were better than a single number, and were consistent, it would be a great service from the consumer point of view. Perhaps difficult to get started from the business one though, before the volume is large enough/process easy enough?