What Not to Wear on a Date

By Terri Trespicio for GalTime.com

Am I overdressed?Am I overdressed?

Could you talk a little about what to wear on a date? How important is it to be comfortable? Also, if I'm dressing up to appeal to someone else, am I kind of not being myself? I tend to look somewhat casual, but if I dress up too much than perhaps I'm sending a false picture of myself.

--Jenna P., Boston, MA

Some people will say: Ah just be yourself. Be comfortable. The right person will love you for who you are, not what you look like.

Do not listen to these people.

How you present yourself has everything to do with how people perceive and treat you. Sure, I like to be home in a tank top and no bra. That's comfy. You better believe I'm not leaving the house like that. And it's pretty safe to say that unless they're on their way to a big board meeting or a black-tie affair, most people tend to be fairly casual. This is besides the point.

The only time you really want to factor in comfort is when you plan to walk 5 miles or are investing in Goretex boots for a climb up Mt. Washington. Unless you routinely buy shoes that don't fit or clothes that are uncomfortable, this is not an issue.

Comfort is Overrated Comfort is Overrated Comfort Is Overrated

The comfort you're referring to has more to do with confidence than it does elastic waistlines. Dates--especially first ones--are definitively UNcomfortable. By design. Showing up in sneakers and jeans is not going to remedy that issue. If you can bear the discomfort of a date with a stranger, you can bear up in heels for a few hours.

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Why? Because how you look matters. Attraction is first and foremost visual. It just is. A man may not know Louboutins from Lululemon, but he knows a woman who's made an effort when he sees one. And he can easily spot someone who hasn't. Yes, a great sense of humor, intelligence, a loving nature and good soul are all important. But no one knows that when you walk in the door. They just see you--and if it's you in a pair of ill-fitting jeans and a top that screams "I just threw this thing on," well, you have limited yourself and the potential of this date.

Going out, meeting new people, and sussing out attractive potential partners isn't about comfort. It's quite the opposite: It's about getting OUTSIDE your comfort zone. That's where the magic happens. You want the ultimate in comfort? Stay home.

I'll even go so far as to say that you should wear something that's just uncomfortable enough that it makes you aware of your body and your posture. A pencil skirt with a slit up the back will make you aware of how you're holding yourself on a bar stool, for instance. A fitted dress ensures you stand tall. Slight discomfort heightens awareness of your body, your physicality, and this can be a very good thing.

Now, that said: Nothing screams insecurity like someone who's in clothes they don't believe they can pull off. Hobbling down the street in sky-high heels is not a sexy look. Aim for confidence over comfort. Meaning: Yes, you should be able to walk without support, but you also want to wear clothes that flatter you and that help you look and feel more confident. It goes without saying that you shouldn't invest in clothes that do not fit or cause you serious pain.

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If you don't feel sexy in fitted clothes because you're sensitive about your belly, then you wear a top that flatters your midsection while playing up your rack, if that's one of your assets. Great lipstick if you've got full, sensual lips. I mean, this is basic fashion advice right? Play up what works, play down what doesn't. It doesn't matter if you wear kitten heels or stilettos--it's whatever puts a little swing in your hips and makes you feel like sex in a bottle.

Hmm...Hmm...Take this quick test when you look at an outfit:

-- Could I just as easily hang out on my bed reading magazines in this? (Change out of it immediately.)

-- Would I wear this very same thing to a baby shower or a work meeting? (If yes, it's probably a little dull.)

-- If this outfit could speak, what would it say? "I'm on my way to a 6-month cleaning" or would it simply purrr or perhaps even growl. Go with that one.

-- Did I wear these shoes to clean the garage? Would they be aptly described as "practical?" Change them. Shoes are the punctuation to your outfit. They should say something, and it shouldn't be, "I wore these for five hours in line for the iPhone 5."

Is This Really Me?

It's clear what you're really getting at here, and it's not so much what looks good on you (because I think you already know, and if not, go shopping with an honest and stylish friend). You're really asking, "If I make an effort, am I not being true to who I am?"

What you're assuming is that there's only one "true" you. That the "real" you is in your underwear watching Honey Boo Boo Child, or in work pants and a sensible button down eating a pita pocket. Well, tonight the "real" you is going to wear a silky top and a skirt, and slurp down oysters.

You aren't choosing whether to be you or not to be you when you get dressed to impress. The idea is, how do I broadcast my best self. You don't become someone else by sliding on some heels. You simply unmask another side of you.

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I'll go so far as to say this, too: Not making much of an effort is passive aggressive. It says, "I shouldn't HAVE to make an effort." Or worse: "Prove to me why I should." Eeesh. This sends a message not just about how you feel about your appearance, but about how you view relationships. If you don't make an effort now, why would you make an effort at any other point? It may start with lipstick and raking a comb through your hair. But it becomes how much of an effort you make to listen to and understand him, how invested you are in keeping your passion alive. Being accountable and willing to rise to the occasion matters.
pink flatspink flats

Girl Shows Up to Date Unshowered

Case in point: A male coaching client of mine went on a first date recently--a brunch date. Turns out the girl figured since it wasn't a Saturday night, she had a license to be sloppy. Unless you're a French model, the just-woke-up look won't work for you or most. He reported that she made no effort--no make up, hair a mess. He got the impression she fell out of bed with a hangover. It was a turnoff.

"Is it crazy to want a girl who looks put together with some effort? Just not sexy to me if you didn't try," he wrote to me.

No, it's not crazy. Not at all. You don't have to get all tarted up in a way that's unnatural to you so that you can get the guy to like you. But you do have to turn up the dial. And if your instinct is to reach for what's merely "comfortable," rethink it. When you make an effort to really shine in your appearance, you send a message not only that he is worth that effort, but that you are, too.

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