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Okay, I'll bite. What cities that could be defined as medium-sized have those stores?
I don't know of any cities the size of Greensboro and Winston-Salem that have all those stores; I'm pretty sure there are none. Maybe some have one or two of those stores though. I know Augusta, GA is getting a Michael Kors store.
I suppose OP means high end stores such as Neiman Marcus, Armani, Saks, Thomas Pink, Nordstrom, Barneys New York, Michael Kors, or Bloomingdales.
It also occurred to me that while Greensboro/Winston-Salem have some high end demographic as evidenced by existing retailers, does not have the a lot of the type of shopper (new money) that drives business at some of the stores you mentioned. I for one am thankful for that...
The trend these days in retail seems to be getting away from malls and more in the concept of large stores set back from the road in strip plazas with stand-alone places like banks and restaurants up front by the road. Which works better in places that don't see a lot of snow.
The outdoor mall seems to be a relatively new thing at least in more northern climates, I visited one in Anderson IN over the summer that was rather nice, parts of it were like an open mall with roads between the buildings and parts were like the strip plazas. I don't think any of the place was more than five years old, but that area is growing, places that were farmland in 1999 were loaded with retail in 2013.
I'll say this. Greensboro has a heck of a lot more shopping than where I came from in Martinsville, VA. Of course, that's to be expected since Martinsville has never recovered from the collapse of the textile mills and furniture factories. Of course, my wife and I don't have a lot of money to throw at these high end department stores, so we really don't need to shop at places where a pair of jeans might cost ya $200 bucks or more.
I'll say this. Greensboro has a heck of a lot more shopping than where I came from in Martinsville, VA. Of course, that's to be expected since Martinsville has never recovered from the collapse of the textile mills and furniture factories. Of course, my wife and I don't have a lot of money to throw at these high end department stores, so we really don't need to shop at places where a pair of jeans might cost ya $200 bucks or more.
People from Martinsville shop in GSO. They also go to restaurants/bars and other general entertainment in GSO.
From the earlier comments in this thread (from years back) comparing Richmond to GSO and WS, the Triad should be considered one shopping area due to the proximity of the cities...so when someone says "Richmond has 3 Dillard's" (even tho Dillard's is not a standard I would aspire to) the Triad actually has 4 Dillard's - WS, GSO, HP, and Burlington. Richmond does not have another comparably large city 20 minutes away like exist in the Triad, so it's really hard to compare the two.
I think shopping in the Triad is pretty comparable to other cities of similar size. People just like to complain.
Greensboro/Winston do okay on the Shopping end I've always though. Four Seasons is still the only 3 story mall in the state and I love that place. And what I'm surprised no one has yet brought up is that the reason that the Triad dosent have more retail or even high end retail is that unlike Richmond which was mentioned for some reason earlier Richmond kind of stands by itself. But with the Triad there are 2 larger more robust and more attractive Retail Hubs close by as Raleigh/Durham is just an hour away and Charlotte an hour and a half. As someone else mentioned retailers look at $ per household and also geographic region. So The same way Greensboro has benefited over the years by normally getting all the great concerts even when Raleigh and Charlotte don't because it's smack dab in the center and can draw from 3 large population centers. In the reverse if you can't find it in Greensboro or Winston one could make the relatively short Drive to Charlotte or Raleigh/Durham and find all the SAKS, Nordstrom, Neiman Marcus etc they could need.
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They also go to restaurants/bars and other general entertainment in GSO. 
