DEAR SOMEONE ELSE’S MOM: Whenever my sister and I go out to a dressy event, like a wedding or anniversary party, my sister always wears the same outfit. It isn’t so much that it’s a little out of style so much as it makes her look like a middle-aged woman, rather than someone in her mid-30s.
She’s a single self-employed mom, and I understand she doesn’t want to spend a lot on herself, but I keep thinking she’s going to be single forever if she doesn’t make a little effort to look her age when she goes out.
Do you think it would be tacky of me to offer to take her shopping, my treat, to get at least one decent outfit that lets people see how young and pretty she really is? She’s smart, sweet, and has so much to offer, and she just doesn’t seem to get it or especially care. Add to all that that she’s got a killer body, which I’ve always been jealous of! --- MY SISTER’S NO FRUMP
DEAR MY SISTER’S NO FRUMP: It sounds as if it’s just possible your sister isn’t as interested in getting out there, romantically speaking, as you think she should be. If that’s the case, she might be perfectly happy with her dressy outfit.
Your offering to take her shopping may work in the context of a birthday or other special occasion treat, provided you let her do the choosing, without judgement.
What could potentially be a more useful approach is if you encourage her to update her look as a small, well-earned treat to herself. If you go shopping with her, you can perhaps remind her that she works hard, takes care of her family, and now deserves a little something for herself. Even if she doesn’t replace the whole go-to ensemble, perhaps new accessories or a partial switch-out will make a big difference, and more importantly, help her feel like it’s okay to reward herself once in a while.