Let's talk about jeans.
Being a non-anorexic girl with wide hips and a pretty big butt, I've ALWAYS had a difficult time finding jeans that fit me well. Jeans, then, are one of the few items that I advocate "splurging" on. My definition of splurge in this case is anywhere from $50-around $100.
When you find a good pair of jeans you can wear them 3-4 times a week and not look like a homeless person. A good jean splurge is a pair that you can wear on casual days, but can also dress up for nights out.
My suggestion, if you're oddly proportioned like myself, is to go to a store where they know what they're talking about. My absolute favorite is Lucky Brand Denim, on the corner of Newbury and Fairfield Streets.
You can go in there and tell them what kind of jean you're looking for--in my case, mid rise boot cut--and they'll grab a few options for you to try. The staff is honest (at least that's my impression), friendly and don't try and make you buy 20 other things while you're there. You walk out without having broken the bank, and you get a good pair of jeans, which, let's face it, makes every woman happy. Here's the pair I bought most recently:
The Lola Boot--perfect for the girl who wants a higher rise to her jean (not mom jean-ish, I promise you) and a skinnier leg (no need for extreme flare, this is not 1975, people!)
The options at Lucky usually run around $100--which is not necessarily a "bargain," but its much better than paying $250 for a pair of True Religions or Rock & Republics, which I'm convinced, by the way, are made only for girls who are 5'10" and weigh about 80 lbs. But I digress.
Another, CHEAPER jean option that I love is Express. They re-vamped their line fairly recently, adding different rises and more washes. So they also have a mid-rise jean that I love (the W31 Curvy) and are always having sales. A basic Express jean will cost around $50-$60, but they sometimes have $20 off sales on all denim.
The nice thing about Express is that you can get a good quality pair of jeans for a reasonable price, but they don't look cheap in any way. A dark jean from Express dresses up really nicely. A lighter wash is perfect for going to class or going out for a casual lunch. They have plenty of options for all different-sized gals, and you can usually get a great outfit from there for well under $100. Plus, their clearance racks are AMAZING.
A note about buying jeans: don't buy a pair if you don't love them. If you just "kinda like em," you'll wear them once and then bury them in your closet. Trust me, I know.
The ideal jean should fit nicely around your waist--a little snug when trying them on because most jeans will loosen up about half a size. If you're a heels girl, like me, buy them a little bit long, so they'll look good once you're hiked up in the big girl shoes. Or better yet, bring your favorite pair of heels with you when jean shopping.
And remember, don't EVER let a salesperson pressure you into buying something you're not sure about. She didn't work hard for your money, you did.
EXPRESS: The Shops at Copley Plaza, Downtown Crossing, Cambridgeside Galleria, Arsenal Mall
LUCKY BRAND DENIM: 229 Newbury St., The Shops at Copley Plaza, The Mall at Chestnut Hill