KatieKat, I don't know your age, but I recognize the signs of a stage I went through in my late 40s & early 50s, when my body went haywire and clothes went from being fun things that always fit, to unreliable items I had to strategize about. Much of the fun went out of shopping, as I came to terms with being an aging gamine trying to salvage some of her attractiveness without losing too much of her dignity. If this is your situation, I can tell you: it gets better eventually! Hormonal storms come to an end, and there is calm on the other side, but it takes time. Be kind and patient with yourself as you sort things out. Here is what worked best for me in the process: 1. Buying pants in multiple sizes, so there's always one that fits; 2. Looking for fashionable silhouettes that don't hug the middle (much easier this season than earlier.) 3. Indulging in delicious and flattering color around the face--whether in a scarf, a haircolor, a beautiful top, or a great new lipstick; 4. Buying better quality clothing (I finally had to admit that I needed clothes with some structure and better cut, and it became sort of a game to find the best possible quality where it really matters--trousers, jackets, dresses, etc.--for a price I could afford, by shopping in consignment shops, sales, and online discount sites. All of this has taken longer than shopping did in my 20s & 30s, but it's worth it. If you are not middle-aged, but just in a temporary fashion rut, things should go more easily for you! Starting with your shoes, for example, may I suggest going somewhere with a huge selection, and trying on pair after pair until you find shoes or boots that are both stylish and super-comfortable? (There's always one out there.) Then concentrate on an amazing jacket--leather, maybe?--that makes you feel cool because the texture, color, & cut are perfect for you. Then add a pair of premium jeans or pants that don't tug at your waist, and make your legs look long. Finish with a top or scarf in the color (it needn't be bright) that makes your complexion & eyes glow. It sounds simple, but having just one great outfit that dependably makes you look and feel attractive can be the first step out of a rut. Good luck!