If you're expecting some grand congregation of prepsters you're not going to find it. There's a Vinyard Vines in Georgetown if you want to score a pink shirt or two.

Anonymous wrote:Get a yacht, pop a collar, and knock back a couple of gin and tonics old sport.

He's too young to drink.

Stay in Annapolis - definitely a preppy, boaty crowd. Also head over to Easton in MD, as well as the Delaware beaches. In DC it's Georgetown. In VA it's Old Town Alexandria.

Get a yacht, pop a collar, and knock back a couple of gin and tonics old sport.

Howard County maybe? Columbia?

Seriously you are so weird.

This poster has been obsessed with what is preppy for a long time. At one point he asked where people with popped collars hang out. It's a quirk.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Preppy and Baltimore don't exactly cross paths.

You clearly do not know Baltimore. Plenty of preppy old money, probably more so than in DC.

Yes more "old money". Old money preppy is not downtown spending it out in the burbs yes, but I would not describe the Friday Saturday night crowd as preppy.

I don't think you have a clue what you are talking about.

Anonymous wrote:

Anonymous wrote:Preppy and Baltimore don't exactly cross paths.

You clearly do not know Baltimore. Plenty of preppy old money, probably more so than in DC.

Yes more "old money". Old money preppy is not downtown spending it out in the burbs yes, but I would not describe the Friday Saturday night crowd as preppy.

Anonymous wrote:

If you have to ask...

I'm not from the area friend.

Anonymous wrote:Preppy and Baltimore don't exactly cross paths.

You clearly do not know Baltimore. Plenty of preppy old money, probably more so than in DC.

If you have to ask...

Preppy and Baltimore don't exactly cross paths.

This is such a strange question... what do you mean by preppy? Country club crowd?

Georgetown comes to mind.

I know it's not typical on the travel forum to ask about this area, but I'm headed to St. John's in Annapolis in the fall. I'll have eay access to Baltimore and DC. My weeks will be full of work, but I do want to explore the area on weekends. What are some preppy hangouts (shops, restaurants, etc) in Baltimore and DC? What's the preppiest mall in the area?