<font face="Verdana, Arial, Helvetica, sans-serif" size="2">Originally posted by SPIT:
Unless you're dressing like a slob, I think it matters little. I commonly dress in jeans and "polo" or something similar, and have no real hotel status. However, I'm frequently upgraded (without asking!).
I think most hotels know there are numerous large companies where jeans and casual wear are the norm... especially out west.
My belief is it has to do more with having a friendly positive attitude. I see so many people who are gruff at check-in, try to act important, or "talk down" to the clerk.
At nice hotels I always check-in with a smile, say "yes", "please", "thank you", "much appreciated" rather than the slang language I often hear. I usually even start off on arrival saying, "Hello, how are you doing today?" Afterall, they're working, which can be dull at times, and I'm about to be pampered at their hotel. I enjoy trying to brighten their day. In return, an upgrade often appears.... usually to my surprise as I open the door to find a suite!</font>
I agree. IME, it doesn't matter at all how you are dressed, but how you present yourself as a person that counts. My wardrobe has been described as 'rock star casual' and I usually dress only for comfort when traveling. I don't get any fewer upgrades than my colleagues who wear business suits. In fact, many of them are surprised that I got a suite and they didn't. Perhaps it's because I always show my NWA worldperks elite card, although i'm only silver. Perhaps they think I'll appreciate it more since I sometimes look like I've never seen the club floor before.

Either way, I get the upgrade. I think it's because I am friendly and polite when checking in. People skills trump a clean suit every time.