I'm an ex-full-time kilt wearer. When I started, I was the only man working in an office of women, and they had no problems at all. In fact, when I left that job, on my last day all the women wore tartan skirts and knee socks in order to join the fun. The rest of my work was in a restaurant and because the dress code was to wear the company shirt and khaki bottoms, I was able to wear a khaki Utilikilt. My co-workers thought it was great and supported me wholeheartedly. During that time I also spent nearly a year and a half (and 7,000 miles) backpacking outdoors, and wore a kilt almost the whole of that time, through all weather and terrain.

I started my kilt collection slowly, but now own two wool kilts, three P/V kilts, and two Utilikilts. Starting out I'd try not to wear the same kilt twice in a row but honestly, why not? Most people wouldn't expect you to have more than one (or wouldn't think about it). As long as you change shirts and hose I don't think anyone would give it two thoughts.

As to what I wear with them: pretty much anything that I'd wear with anything else. When it's hot out I rock the kilt, t-shirt, and sandals combination. The kilt is a garment, not a costume, so just wear it.