The trick to dressing well on a date is to combine good style and making it look like you didn’t over think it.
I would be pleased to over think it for you, so that you don’t have to.
I think it goes without saying that it is best to wear clothes that flatter you and fit well. Show off your good assets.
Make sure you comb your hair too. My last significant girlfriend told me that she thought I had nice hair while we were on our first date.
Oh, and while we are on the subject, make sure you take some breath mints.
…Alright, back on track.
Another thing to make sure of is that your clothes are comfortable. This serves two purposes. First, you will be comfortable doing whatever it is you end up doing. Second, when your clothes are more comfortable, it helps you feel more comfortable being with this new woman.
The last thing that should guide your decision of what to wear should be that you feel like you look good wearing whatever it is you wear. It doesn’t have to be flashy or exciting, but you should feel like you look good in the clothes you decide to wear on a date. Your dates will go better when you feel sexy and attractive.
Here are some more guidelines that you may consider following beyond these basic rules.
Show different sides of your personality.
If I meet a woman out at a bar, and I am dressed casually, or dressed looking like a rocker in my leather jacket, I often plan the first date for some evening after work, when I will be dressed in a suit and tie. I like to show, with my clothing and style, different aspects of my personality.
This is similar to what I wrote yesterday about wearing accessories that are out of place with your overall look.
There is more to who I am than one particular stereotype, and I want to convey that with the clothes I choose to wear. At this time, I am working to convey breadth of character (depth comes later).
Not many people are always the same person all the time. We vary, sometimes we are fancy, sometimes casual, sometimes upbeat, sometimes mellow, sometimes professional, sometimes sporty, and sometimes slackers.
You can communicate this by wearing a different style of clothing on your date than you did when you met her.
Dress with a goal in mind.
On most first dates, I have a very specific goal in mind. I want to get to know the woman well, and to let her get to know me well. I want to build a connection quickly. I want us to feel like we know each other better after 1 date than she did the last guy after 10 dates.
With this in mind, I often tone down how I dress. I don’t dress as fancy or as flashy as when I met her. I want to communicate that this time together will not entirely be about flash and fun, but about substance.
By toning down my dress, I mean less accessories, less hip, fashionable clothing, less elaborate shoes (not less *nice* shoes though). Essentially, I shift away from dressing like one of the extremes of any stereotype.
Of course, this tactic fits into my overall goal of building a strong connection and rapport on that date. If you have other goals in mind, you can probably think about how you can dress to help communicate those goals.
Style is Communication
You may have noticed that pretty much everything I have written about style this week comes from the perspective of how to communicate to other people with your style.
Clothing and style is a *big* part of the non-verbal communication that we put out in to the world for everyone else to see and understand. No matter what we wear and how we wear it, we are communicating to women something about ourselves.
For a complete dose of learning about the language of style, get Dress For Success. It is a set of DVDs that goes in depth into style, and how it communicates with women.
Dress For Success costs less than a nice pair of jeans and shoes, and you will never buy the wrong jeans or wrong shoes again after watching this program.
Lance, who put this program together, offers a money back guarantee on the DVD program. You’ve got 6 weeks to try it out, and if it isn’t the right thing for you, you can return it for a refund. You’ve got nothing to lose. Except maybe your old crappy clothes.