Where do we go to help them figure what looks good and where to get things that fit? Especially virtually/online? (We are still isolating as much as possible due to the pandemic and having at-risk kids). Thank you!
Many great suggestions here. My sweetheart got up the courage to use the dressing room in a small shop at the mall one Wednesday morning. The only other person in the store was a burly man. She tried on one dress and we bought it and she loves it. Then the shutdown began. We remain isolated due to our own health concerns, and in support of others whom we don't want to infect.
She has stuck with men's pants, and wears skirts that have very adjustable waists like elastic and drawstrings.
I sew, so I make and alter her clothes, but I can't keep up with her appetite and body changes. We hired an upscale dry cleaner's tailor to alter some shirts, and they came back poorly done -- even after I returned them to be redone twice.
A few more ideas:
Before the shutdowns, I was hyper-attentive to how she interacted with the merchandise. She followed me as I deliberately walked slowly through the racks, stopping when I noticed that something caught her eye. We discovered that her shirt and dress size is usually exactly one size larger than mine, so I tried on clothes for her in my size to help her see what they looked like "in real life". I explained how each item felt on me: stiff, energizing, constricting, delicate, rugged...
She doesn't have the patience to try on a box full of clothes or sort through huge racks. I enjoy doing both.
She continues to buy clothes from her favorite Man Brands that have some more feminine fabrics.
Best wishes!