From a guy’s perspective, do heels really make that big a difference when it comes to a date-night outfit? Do you really care if we wear heels rather than, say, boots or flat sandals? And what if a particular pair of stilettos makes a girl as tall as—or taller than—her man friend?
I would imagine that when you go out on date night, whether it be a first date or just another date with the person you are currently getting to know/seeing/married to/settling with/employed you via Craigslist/etc., you have a certain set of expectations. Now, don’t get it twisted—when I say "expectations," I don’t mean the kind of exaggerated expectations that tend to follow the typical "women be shopping" dialogue. Simply put, you want the other person to take you and the time they spend with you seriously.
So, while the guy you’re dating isn’t going to magically show up and be Michael Fassbender, Daniel Craig or (at the very least) Paul Rudd, you’d hope he took things seriously enough to impress you with his appearance. I think the same thing applies in the reverse scenario. Whether or not he is expecting heels, and he probably is because "sexy shoes" are, like, the bare minimum of "fashion" signifiers that the average man understands, I think wearing them is the right move. You and I both know that you put thought—maybe too much thought—into what you’re wearing to date night. Your date probably does not. But when he sees heels, I think it’s safe to assume that he knows you mean business.
Personally, I have nothing against boots or flats. Actually, I take back the flats part. A cute pair of sneakers or sandals beats those fancy socks masquerading as middle school ballerina practice slippers any day. But for those of you looking to lead by example, I think they fall a little on deaf ears.
As for the worry of being as tall or (gasp!) taller than your man friend, I wouldn’t sweat it too much. Everyone knows someone who knows that weird short dude that is creepily obsessed with taller girls. You hear about him and it sounds shocking and bizarre. To be honest, I’ve never met a guy, short or tall, who had a problem with getting together with a tall woman. Seriously! Let’s chalk that one up to ridiculous gender roles, forget about it and talk about how awesome Hillary Clinton is.
Lawrence is a writer living in New York. Got a guy-related fashion question for him? Leave it in the comments, tweet him at @SartoriallyInc or email him on email@example.com.
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