The first thing to understand is that the first time is the hardest for ALL of us. And most of us, even after we've told you that "The only thing to fear, is fear itself." Still occasionally get butterflies in our stomachs at the thought of going somewhere we've gone a dozen times before, let alone at pushing the envelope yet another notch. But as we keep telling new members, while we come up with lots of things to be afraid of, there's really no reason to be afraid.
That said it's best to start slowly and work your way out into the world, because half of the battle is building up your own confidence. If you can just ACT like your walking to the corner, going to the grocery store or getting gas in a skirt is the most natural thing in the world, nearly everyone will respond in kind. Similarly, if you act furtively, like you have some reason to be embarrassed at how you're dressed, people will take you up on that invitation as well. Think of it this way, about half of the world's population goes out and about in skirts all the time and no one things any the less of them for it. The fact they happen to be women is entirely beside the point. When they wear pants no one thinks about that either; why should it be any different for you. So don't be embarrassed that you start slowly and carefully -- you'd be foolish to do otherwise because every town is different -- the fact is we all have started that way and that the crucial thing is to start.
Next you have to find a style. If you look at the Pics and Looks section you'll see that members of the SkirtCafe wear and look good in a wide variety of skirts and dresses. So pick a style that suits you and try it out! Many members have found it works well to start with the simpler styles that look like pants that the factory forgot to separate into two legs, such as denim skirts, because they look so much like menswear. Like I said above, the crucial step is to begin and in a place and manner you can feel reasonably comfortable and confident in and then build on it. Once you get comfortable, don't be afraid to push your own boundaries because that is how you will find a distinctive style.
Another plan is to look around at what women your age are wearing and try to imagine how it would feel to wear the clothes that appeal to you. Window shop, look in magazines, catalogs and online. How do you think women discover their styles?
Speaking of which, ask the woman or women you're comfortable talking to about personal matters for their advice. Especially if you like the way they look and dress. Most women seem to get a kick out of seeing me in a dress so don't be afraid to ask for expert advice.
When you're looking around for that elusive personal style, resale and thrift stores are a great place to look because all kinds of things wind up in those shops and they are great bargains so the unsuccessful experiments don't cost much. And in thrift stores you're usually supporting a good cause.
Look online for the standard dress sizes and where your measurements put you. Then realize they're only a starting point. Especially the more expensive brands of clothes go for "vanity sizing." That is, their 10 could be a standard 14 or who knows what so that the buyer feels thinner in it. The brand carried in department stores generally run true to size, but reviews on the store's website can tip you off to the clothes that don't and sometimes just the cut or style can make a big difference. For instance, a sleeveless dress with generous armholes might work better for you in a smaller size especially, like many clothes are it has a little spandex or elastane woven into the fabric. Remember, you won't fill out the bodice like the fitting models did.
So you might think that skirt sizes would be more consistent. HA!! They're the WORST for inconsistency. When you go skirt shopping bring along your tape measure so you can measure the waistband on the hanger and multiply by two. If that number is close to your waist size or wherever you expect to wear the skirt, try it on. That's right, try it on. The staff will have no qualms about telling you where you can do that. Remember, they are there to help you make a purchase you will be happy with, not to enforce social norms. The latter is bad for business.
Above all else, don't forget that we're practicing that manliest of mantras, "No guts, no glory!" Or, to be more specific, "It takes balls to wear a skirt!" Yes, most of us have been told that at least once.
Good luck and welcome to the café!
(that's where the story behind this post took place)
