Reader Question: “She doesn’t dress as well as me”

Dear Megan,
What should I do when I out-dress my date? I know this is subjective, but sometimes I feel like I have dressed more fashionably for an occasion than she has (even though she knew ahead of time the nature of the occasion).  I have never said anything, except to compliment her. My thought has been to lead by example. Is it ever appropriate to drop her a hint, and if so, how should it be done?

Henry Higgins, is that you?

In My Fair Lady, Henry Higgins (the dashing Rex Harrison) picks an unsuspecting…homeless woman? Pigeon girl? (It’s been awhile since I’ve seen it…) played by the fetching-as-soon-as-you-wipe-away-the-one-dirt-smudge-on-her-cheek Audrey Hepburn. Higgins has bet his fancy doctor friend that he can pass Hepburn off as a high society lady by teaching her how to speak, dress, and act “properly.” Of course, he pulls it off. She gets upset. They fall in love. There is singing and choreographed musical numbers.

(You may recognize the plot from its modern-day retelling, the 90s’ classic “She’s All That” starring Freddie Prinze Jr and…that chick who was in Josie and the Pussycats.)

THE POINT IS, are you trying to date this lady, or are you engaged in some fancy people social experiment, trying to better the life of this poor girl who you’ve taken pity on to date? If it’s the latter, I’d let go of any thought of “leading by example.”

(Actually, it surprises me that you’d date someone whose style veers so wildly from your own. If being well-dressed is as important to you as it seems to be, wouldn’t you naturally go after a girl who dresses to your sartorial standards…?)

In any case, don’t compliment her on the clothes you don’t like! That’s lying, and you’re not doing yourself any favors besides. I’d say, if you really like this girl, but simply want to help her declare peace in her war zone of a wardrobe, then you might need to wait till you’ve been seeing each other for awhile.

I have dated guys who’ve dressed more casual than me (think sweatpants and windbreakers…everywhere) and guys who’ve dressed waaay nicer than me. If any of them had asked me to dress down, or up, to match them – especially at the beginning of our relationship – do you think I’d have listened? Or do you think I would have swiveled my neck around and gone all, “Oh no you didn’t!” in a sassy-like manner. Yeah. Probably the latter.

The thing is, if I like a guy, I’m going to dress to please him to some extent. Not change everything about my wardrobe, but if he says, “Aw babe, I love how you look in that dress,” I’m probably going to wear that dress more often. Ya dig?

So, do what us girls do when we don’t like how a guy dresses. Compliment the hell out of her when she wears something you like. Maybe even buy her a few things that you think are more appropriate for her, then suggest she wear them on specific occasions. (ie, “Hey honey, why don’t you wear that skirt I got you to dinner tonight?”)

If she doesn’t take the hint, and the way she dresses still bothers you, she’s probably not the right girl for you anyway. You never want to be with someone who you’re constantly trying to change. And couples have broken up for much less (and sure, more) than how a person dresses. Relationships are about compatibility; if you cringe every time you walk out the door with this girl because she’s wearing a brown belt with black shoes, well, I wouldn’t put odds on you guys making it down the aisle.

Tell me: have you ever dated a girl that dressed way different than you? Did it bother you? Did it change your style at all? Did it change hers?

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