Q: My fiancé and I have decided to have a non-traditional wedding party. My brothers are my men-of-honor and his college-aged sisters are his best-maids. I am very excited about this decision—our wedding is a “fusion” wedding and having my brothers at my side reflects some of my family’s cultural traditions.

However, even though my future sisters-in-law are technically my fiancé’s best-maids, I’ve found myself tangled up in the process of choosing their dresses. Initially, my fiancé and I decided we’d tell his sisters the wedding colors and let them wear what they wanted, within reason.

Well, the definition of “within reason” has begun to cause issues. I have a laid-back style (my day-to-day fashion is reminiscent of the failed GAP “Dress Normal” campaign) and rarely wear makeup, even at work. My future sisters-in-law tend toward style choices that are a little edgier, with higher hemlines and lower necklines than I’d wear, and a love of heavy contouring. On any other day this wouldn’t be a problem—they look and feel great how they choose to dress, and I feel the same way about my no-fuss approach. But when it comes to best-maids dresses and makeup I am worried that our two aesthetics will clash, especially now that my future sisters-in-law have started sending me dress ideas.

The first few dresses they suggested were easy vetoes (they weren’t the correct colors). But the dresses had non-color related issues too—they were VERY (VERY) tight and backless, which wouldn’t go over well with my conservative family. Now I’m worried they’ll come back with appropriately colored but otherwise inappropriate options, even though my future mother-in-law has been accompanying them on shopping trips and ostensibly pre-approving dresses.

How can I politely point them toward more “appropriate” options without seeming judgmental of their wardrobes? I honestly don’t care whether they wear a one-shoulder dress versus a boatneck or tea-length versus full-length or whatever. What I do care about are dresses that look like classic bridesmaids dresses and not like something a daring starlet would wear to the Met gala.

(Relatedly, I am now thinking I either need to have a frank conversation with them about makeup or throw money at the problem and pay for them to get their hair and makeup done with my mom and me. I am planning on keeping things minimal in that regard, and I’m not confident they’ll do the same without guidance.)

Any suggestions for how to handle things tactfully?

—Anonymous

A: Dear Anonymous,

Just pick the damn dress.

If you let them wear what they want, it’s not going to be A-line, tea-length, whatever. It’s going to be tight and short and revealing. If that’s not what you want them to wear, pick the outfits.

Saying, “Wear anything you want! …As long as it fits all of these bullet-pointed requirements,” is actually way more restrictive and complicated than just picking a dress and telling everyone to order it in their size. And trust me that this won’t end with one round of specifications. If your style is so wildly different from theirs, they’ll find a way to pick an A-line, tea-length, whatever dress that is still too low cut or too tight or too flashy for your tastes. And further refining and specifying and, “Weeelll, not really like THAT,”-ing will get really old, really fast.

Same goes for the makeup. If you want your in-laws to feel good about how they look, give them no restrictions. If instead you want them all to look a certain way, get it done. There is no middle-of-the-road option that isn’t terribly insulting (and could you imagine how you’d feel if the tables were flipped and they were trying to delicately tell you not to look “too plain”? Ouch).

If you really, really just want these folks to feel comfortable in their own skin, then you have to embrace the fact that feeling comfortable to them involves a lot more makeup and a lot less skirt. If that won’t fly at this wedding, pick the damn dress.

—Liz Moorhead

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