17 Things Guys Say They Hate To See You Wear On A First Date

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I know what I like to wear, but I must confess, I don’t know what guys like me to wear. And it’s not like anyone should completely change their wardrobe for a date or turn off their true selves, but sometimes it’s worth it to dress safely — shall we say agreeably? — on the first meeting. Think of it as going into an introduction with a blank slate, with baby steps, with caution. Because even guys who say they don’t care about clothes kind of do. Here’s what some of my guy friends said when I asked them were first date fashion no-nos:

Related: The Ultimate First Date Guide: Everything You Need To Know


Anything too revealing. Short skirts, cleavage-bearing anything. Seriously —  you may think you look hot (and you probably do) but it’s not a great first impression. My friend Rich told me, “I like a slow reveal — and to do a little work to get there.”

Also: anything that totally hides the body. “No sweatpants!”

Huge purses. They make you look high-maintainence which makes guys think you’re an expensive date blahblahblah, not fair but true.

Related: 6 Things Girls Should Never Wear On A First Date (If They Want A Second One)

Anything too dressy. If you’re going to a sporting event, skip the pearls.

“Whore Lipstick.” (This was described to me as “lipstick with adjectives such as hot, wet, sexy, lusty”.)

Ear gauges.

Related: 12 Last-Minute Steps To Prep Your Apartment For A Guy

UGGs. (This came up a few times.)

A T-shirt expressing any sort of controversial opinion. The example given was actually “I Love Mitt Romney.”

Too much makeup. You might think it looks okay, but guys don’t like to see your face caked in makeup.

Uncomfortable-looking shoes. Do a test before your date — if you can’t walk normally in them, leave them at home.

Related: 10 Things Guys Should Never Wear On Dates

Glitter. This is really hard for me to say — I am devoted to the wearing of glitter makeup. But even I know: On a first date, an interview, or anytime I need to actually impress, I wear normal-person makeup. Don’t stress — the second you get home you can scrub it all off and go back to your more natural, glittery state.

Something that can fall off, slip up, unzip, or unbutton. Even though your date would probably love it.

Something that you haven’t worn before. You never know how you feel in something until  you give it a test run, and you want to feel good.

Related: 10 Things To Always Have With You On A First Date

No bra. Although one of my friends highly recommended not wearing one, I’m going to have to disagree.

A turtleneck. “I don’t need to see Katy-Perry-On-Sesame-Street-like cleavage, but I want to at least get a peek at her neck,” one guy said.

Anything from Buckle, particularly this cowboy hat. (Where do they get this stuff?)

Related: Getting Ready For A Date In 30 Minutes Or Less

Hats in general. Hats are cool, but they are also polarizing. One guy said he didn’t like “those fabric beret-like things” (and I have no idea what he’s talking about), and another said “any hat that is more interesting than the person wearing it” (and I have no idea what he’s talking about). But the takeaway is that guys do have opinions about hats, and while they might be confusing, they’re often negative.

I know this sounds like a lot, but it seems somewhat feasible. They want to see your skin, but they don’t want you dressing too dressy, too uncomfortably, or see too much of your boobs or butt. No hat. Wear a bra. Tone down your make-up. That leaves a lot of room to express your style! As long as your style isn’t Buckle-inspired.