Thanks for all of your advice, ladies! As many of you suggested, I found my answer to my skinny jean dilemma in a fabulous pair by J-Brand. Before my shopping trip to Barneys, I braced myself for a few hours of trying on jeans as I can never, ever find a pair that I like, so I asked a friend to come along (she wears skinny jeans almost exclusively , owns a pair by all of the major denim designers, and also recommended J Brand). She quickly selected a few pairs for me to try on, and I bought the first pair I pulled on.
J Brand sizes their skinnies by waist AND leg opening; the 10” skinny was too much like denim spandex for me, so I opted for the 12” pencil leg (there is also a 14” cigarette and an 18” boot cut).
The extra fabric scrunches quite nicely at my ankles without making me look like I have a cankle, and the back hem slides right over a pair of ballet flats without dragging on the ground and scuffing up the hem.
Although I was tempted by the black and grey, I decided that I’d start off with a dark blue hue called “ink”; after all, replacing my worn-out blue Rock & Republics had been my original intent.
Anywho, I’ve been wearing my J Brands all weekend and they haven’t stretched out at all– they are great! Any trepidation I had about “the skinny” style (ie, how I would look in it) is gone and I’m already thinking about my next pair!