Goodness, I felt the opposite when my sister-in-law unboxed the 38 mm pink sport we bought her for her birthday yesterday: "Damn, that's a really good looking watch. Maybe I overspent getting Stainless Steel on a first generation watch. I could have had a really nice watch for $350."
Really it was lightweight and felt better on my wrist than my SS, and it was really attractive in person. It does have a more "Swatch" type of vibe to it, but I equate that with fun and sportiness, not cheapness. Sis was thrilled with her Sport and didn't even look twice at my SS watch with black sport band. I was the one who kept staring at her watch.
This is similar to what happened with my partner when we went to try on the watch. Before, he was eyeing the black SS, even though we both felt shelling out $1000+ for the watch was a bit too much. Then we got to the store, the person helping us brought out a tray of watches, and my partner picked up a dark-colored watch and asked "Is this the black SS?" I said, "No, that's the Grey aluminum." My partner was like "Really? Wow, this is nice," and never took another look at the SS watches.