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chris, (my designer, metro husband of 1.5 years) loves to see me wear skinny jeans. me, i'm not so sure. of all the ways to draw attention to body imperfections (i.e. excess inner thigh fat, extra hippage, muffintop spillover), skinny jeans pretty much top the list.
key to wearing them--make sure they are truly skinny (skimming your figure, not flesh-choking)--and dark colors help. also always try to take pictures aiming the camera downwards, vs. straight on or from below the subject (especially if that subject is you and you just had a large po'boy for lunch).