How do you dress for a date with a guy? It seems like there are three options that women take. 1. They dress for men. 2. They dress for women. 3. They dress for themselves. Here’s what that means.

I’ve spoken to men about this and most agree that on a first date, they would love to see a woman in jeans, heels, and a simple top (aka “casual pretty”), or in a sexy-but-not-too-revealing dress. Both camps agree that they prefer minimal makeup for both looks. And no Uggs. Men really hate Uggs. Except for Tom Cruise. He wore those in Eyes Wide Shut and he pulled them off. And screw anyone who still hates Uggs. It’s 2013, they’re comfortable as hell, deal with it.

Depending on the type of guy and the type of date, I’ve opted to go the black jeans route, or any pair that makes my ass look gasp-worthy, with heels and a white tee or tank that shows just the right amount of whatever. Then there’s the opposite route of my favorite trick, the LBD. (The secret ingredient is Spanx!)

BUT. Lately. I’ve been merging those last two options: dressing for other women and dressing for myself. Dressing for other women doesn’t mean dressing to allure other women. Unless you’re into women. Most of the time, dressing for women means that you’re wearing the latest trends and trying to dress like all of the cool fashion blogs the kids are doing. These are the outfits that men just don’t understand. “Why are you wearing ugly wooden platform boots?” “What’s with the hat? I can’t see your face.” “Dude, your dress is completely sheer, do you know that?” That sort of thing.

Now then, dessing for yourself means wearing whatever the hell you want, regardless of how trendy or untrendy it is, how comfortable or uncomfortable it is, and so forth. And sometimes, regardless of whether it’s the 1st date or the 5th, I’m thinking, “Eff it, I gained weight, so few things fit, I like this weird skull print shirt and these dangly cross earrings, suck it.”

I still dress for men on occasion. If I feel like it. It’s like having a cheat code. If I’m feeling uninspired or lazy, I’m going to use it.

There are great generalizations in this article, I understand that. Not all men are the same. Not all women are the same. We’re all very special unique people with our own Pinterest boards just bursting with creativity and examples of our awesome style. (I can’t even tell if I’m being sarcastic anymore.) So when it comes to how to dress for a date, here’s what I recommend:

1. Know the venue. You don’t want to wear heels and a minidress and then find out you’re going to Disneyland.

2. Don’t try to squeeze into something that doesn’t fit you anymore. So you had to move up a dress size or two, so what? He’s not going to check the size number on the label. And he’s not going to care.

3. When in doubt, go the breezy jeans route, or wear something that makes you feel irrestible. Everyone should have an emergency go-to date outfit. Find yours.

What’s your date outfit?

 

Images by Nina Leen, Mirek Towski, Loomis Dean, Paul Schutzer