Dear ASM,

How do I politely ask my (smart, accomplished, much-loved) sister to dress appropriately for a family wedding celebration (mine)? I am 46, my sister is almost 50. She runs marathons, works out constantly, and keeps herself very thin, fit, and attractive. So, she looks great, but she also leaves next to nothing to the imagination in how she dresses, wearing super-short, very skimpy dresses, tight low rise jeans, short-shorts, high heels, etc. Basically, she still dresses as she did as a hot 20-something. I’m having a small family wedding (my first) and I’m trying to figure out how to tell her, gently, that I’d like her to wear something pretty that’s neither skin-tight or panty-revealing. The last time I brought this up (for a holiday dinner with my fiancé’s family) she took it very personally and said my request hurt her feelings. But I’m afraid if I don’t say anything, she’ll show up in five-inch heels and six inches of black lace at the post-wedding dinner. What to do? I’d like family discussions of the wedding to be happy, not focused on what my sister was wearing.

Sincerely,
Knee-length Sister

Dear Knee-length Sister,

First off, best wishes on your impending nuptials! That is happy news indeed.

To your question…. While I like your use of words like “politely” and “gently” – they betray a non-bridezilla quality often missing in today’s weddings – I’m sorry to say that the way you do this is that you don’t. There is no polite way to tell someone to dress differently than they do. Imagine if the tables were turned and instead of what I’m sure is a flattering and age-appropriate outfit you wanted to wear, your sister politely and gently asked you to tart it up and show off the goods a bit more. How we dress communicates something to the world. Your sister has had many decades to figure out the message she wants to send; unless she asks for your opinion or expresses a desire to change, you need to butt out.

One sensible run-around you could try is to make an event of buying her wedding outfit together if you think there is a chance you could influence her decision a bit without hurting her feelings. If shopping and lunch or drinks or tea is a sisterly-type day you might enjoy together, give it a try. To pull this option off, though, you’re going to need to get on board the revealing train, gently nudging towards a bit less tight or a bit longer or less lace, not a wholesale change.

Keep top in mind, though, that you’ve already gone down this road and she let you know that your request hurt her feelings. To bring it up again is unlikely to work, is guaranteed to cause more hurt feelings, and is likely to cause bad blood between the two of you – hardly what weddings are about.

Comfort yourself with this knowledge: you have a serious misunderstanding of human nature if you think discussion of your sister’s revealing outfit won’t be happy. A highlight of my extremely sensible Midwestern family’s Christmas is the arrival of a card from old family friends who dress younger and trashier (with her showing off an ever-increasing cup size) as each year passes. Their atrocious taste brings us no end of joy and merriment.

After all, what’s better after a wedding than dishing on everyone there? I, for one, would rather have cousins and in-laws making catty remarks about a happy sister’s Forever 21 attire than conjecturing about why a Talbots-clad sibling seemed so glum.