>>1I tried something else that works in a similar fashion: spending a few hours where successful people congregate. It could even just be a wealthy exurb where there are nice stores or a park, or a part of town where there are a lot of nice stores. If you feel you don't fit in, don't be self-conscious, but start thinking about what you can do in order to do so. Absorb some of the culture and start feeling a part of it. Notice what people do, how people act, what people read, how neat they dress and carry themselves. Again, don't do it to shame yourself, but to learn and absorb. If you go regularly, you won't think of your visit as a vacation and these places as somewhere you'd someday like to live, but a place that you do go already.
Pic related: Mariano Park on Rush Street in Chicago, in the Gold Coast neighborhood