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
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.