What do you think is the most preppy city and the least preppy city

Nantucket is in Massachusetts. I once knew a man from there.
I think you are thinking of Newport, RI.

Martha’s Vineyard, MA is also very preppy.

I’m sure there are plenty.
I think of LA as more fashion conscious in a sort of flashy, showy sort of way. Preppy clothes are generally characterized by being simple, well made, timeless, usually without overt branding. Things like Brooks Brothers suits, peacoats, Burberry scarves, nautical-looking sweaters. Stuff like that.

The state of Texas is probably very preppy you probably never see anyone out in flip flops ,sweatpants or trackpants or sleep, house t-shirt.

Most people there are conservative some in the country will have cowboy hat and cowboy boots look the cowboy look and all out cowboy.

But I think most 98% people there would never wear flip flops ,sweatpants or trackpants or sleep,house t-shirt or tank top out in public.

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Huh?

I am guessing irony.

Least Preppy: Honolulu

Half of this thread is now over.

Moose Jaw Saskatchewan is none too preppy, I’ve been told.

I did some reading on the internet on this topic and they say said New York and Boston is very preppy.

I also got wrong about Texas it is not preppy it is worse than Portland by what others say on the internet.

Anyways I will not say more has I not been to any of those places and just going by what I read others say on the internet.

I just received an invitation from the Tyson’s Galleria to join them at the Grand Opening of their . . . your guessed it . . . Lily pulitzer store.

No idea at all of how I might have ended up on that list. :eek::rolleyes::eek:

Bizarre.

When people in my company have to go to northern Italy for conferences, one of the first things they say is “Dress really, really well.” And we’re a professional outfit. Dressing well is considered basic manners in Italy, far more so than North Americans are used to anymore.

Philly is so beyond dress down casual (in some nabes): Shorts, work boots (not necessarily Tims), t-shirt with a Phillies jersey over it, ball cap on backwards. Not my look, but mostly because of the jersey and hat.

Nap-town? Really?

It’s a town filled with old guys wearing boat shoes and shorts pulled up to their nipples, legislators wearing business attire (which, while formal, isn’t particularly preppy,) and shoeless philosophy students. The midshipmen have a bit of a preppy look to them, but they don’t come out of the Academy much.

Then again, I haven’t lived there since 2004, so things might have changed. I never would have imagined that much, though.

Is there still an Ego Alley in Annapolis? Speedboat showcase of the preppies?

The last time I walked around Ananpolis I saw almost nothing but cord shorts, polo shirts, and deck shoes. There was an astounding amount of Lily Pulitzer, and navy blazer/oxford shirt combos were predominant at dinner.

Tel Aviv:not very preppy.

Well, I suppose for that money we have to go with Riyadh. Preppy dress will get you, at best, imprisoned. . .