My wife is 5'4 and has thick legs, calves and thighs and a really round hiney (in a good way!
) She has problems with traditional shorts. Some are too thin stretching too much and showing too much in the sunlight. She cannot find a pair of boots anywhere that will allow her to zip up on her calves. So that syle is out!
We happened to run into some Terry shorts at a shop we happened to visit while bored. She tried them on and loves them. Nice thick material and construction. Nice comfy chamois. Nice fit around the thighs and hiney. High waisted. Paid about $80. Liked them so much we drove back the next week for a second pair (50 miles).
She's done countless 40-50 milers, a few 72's and an 84 with no discomfort at all. Saddle combo helps too. Specialized Lady's Dolce gel ($50)
I myself used to use the Trico gel shorts, loved them but can't find them in the shops anymore.