I feel your pain. I myself was burdened (with the acute misery that is misfitting denim) for many years before I discovered my love for Rag & Bone denim. It’s soft, I’m always the same size, and they make me look thinner than I am. La victoire.
When confined in price range however, I would suggest your best friend (aside from me) (obviously) is vintage. I don’t mean vintage vintage – those intimidating, but oh-so-holy places which house thousand dollar Dior gowns from the 50’s. I mean the type of vintage you find in fun boutiques that play elvis all day, Op shops (Vinnies/ second hand stores/ charity shops), markets, garage sales, and as I recently discovered, mothers’ closets.
I am so fortunate to have a mother, who not only has impeccable taste, but refuses to throw clothes out. A couple of months I secured 3 pairs of eighties high-wasters, and turned another into a pair of shorts. Snip snip.
So that’s a way to buy free jeans. Or free anything. Steal them from the back of your mother’s wardrobe. Alternatively, second hand jeans at the shops mentioned above are seldom priced over that allusive $100 mark that brand-new jeans can almost never be bought for.
So go vintage! You have to do some digging, but that’s the fun of it.