Dressing Nice

I've been thinking about my wardrobe and how I dress. I realize that most of the stuff that I am wearing is at least a couple of years old, stretched out, and long in the tooth. For 7 years, I was working in jeans, shorts and sandals, basic casual wear and my wardrobe reflects that. Now I work at a big client, I am forced to wear business casual wear, which entails dress shirts, pants, semi-nice shoes, etc, etc. I have a number of ill-fitting dress shirts that I got on sale because they were too big. My tailor asked, "why did you buy such a big shirt?" To which I replied,

"it was cheap."

He said he could tailor it, but he would be taking off nearly 6 INCHES of circumference off the shirt, and because of that much material, the shirt pocket would look strange. oh. and it would cost nearly $40 to tailor the shirt with all the alterations. grrr.

I find that as I get older, I become more dissatisfied with my clothing. I no longer want to buy things just because they are cheap, but I want to buy things that are high quality will last a long time and are just classics so they will always look good. At some point, I'm going to be buying some new dress shirts, t-shirts, dress pants, etc, but with an eye to 1) is the price reasonable? 2) is it high quality? 3) does it fit well? 4) is it classic or trendy? Oh, and no-iron shirts...man, I hate ironing.

Knowing that I do not have fashion sense, I now have to find some fashionable lady to buy my stuff for me. :)