I'm pear shaped and I look terrible in skinny jeans, but I never tried tucking them into boots, mostly because they never make it out of the dressing room. I take one look at myself and put them right back. The problem is not that they hug my thighs, since I always wear jeans that do that. The problem is the tapered leg. I can't believe I've never bothered trying them on with boots. My hips are naturally very wide and I never look good in skinnies no matter how skinny I get, but ever since I lost weight I've been able wear slim straight legs rather than just bootcuts and flares. I have a very small bust, small shoulders,an obvious waist, and, of course, wide hips and thighs. Should I look for a specific kind of boot or does it even matter? Will this kind of outfit make me look more "hippy" than I do when I wear straight leg jeans and regular shoes?