Brooks Brothers Football Leather Briefcase
Not only does the feel remind of days on the varsity squad, but the Brooks Logo says you're smart too. Brooks Brothers $398.00







Donegal Tweed Driving Cap
The perfect cap, even when you're not driving.  This cap screams Ivy League, good times and great beer.
MurphyofIreland.com $49.00







Chukka Boot
This is a much better low boot than Clarks and without the "hippie" feel.  A nice piece of footwear to knock around and the scuffier they are the preppier.
Alden of New England $440.00






Cordovan Oxford
Preppy men know that you can't always get by on boat shoes, sometimes you have to look like a man.  The Cordovan is classic and reminds preps of the shoes their grandfathers wore.
dann-online.com $535.00






Silk Polka Dot Ascot
Yes we know, to wear one of these requires speaking like Thurston Howell III.  Yet, Preppies boiling over with confidence view them as sophisticated and fun, not to mention, they look great with Gucci Loafers (no socks of course).
J Press $89.00



Liddesdale Hunting Jacket
This brand is the first choice of Preps who hunt.  It looks good duck hunting as well an evening out.  Although it is not made of natural fibers means nothing, after all, it's British.
Orvis.com $149.00



J Press Regimental Bow Tie
The old saying, "men who wear bow ties do so because most men don't," holds true.  Bow ties are endearing, classic and studious, all the things true preps love.
jpressonline.com $49.00









Jarrett Bay Belt
No outfit is complete without the sartorial statement of a motif belt which is a preppy way of seeking out other preps.  Best of all, the Jarrett is made by Leatherman in Connecticut.
elizab.com $59.00






The Shaggy Dog
There are many imitators but they just can't get the feel like the Shaggy at J. Press.  What more can one ask for?  A broken in sweater in a multitude of colors that simply looks smashing under a sport coat.
J. Press $180.00





The Nantucket Reds
Another staple that has been imitated.  No one has ever been able to duplicate this salmon colored treasure.  Every prep knows, you can't get that ideal fade unless you've spent numerous hours on the island.
Murray'sToggery-nantucketreds.com $72.50





 The Weekender
Timex, "It takes a lickin" and it's been around forever.  The only true preppy watch.  It looks great at work and for hardcore preps, the grosgrain band is a necessity.
Timex.com $40.00






Tropical Wool 2 Button Darted Blazer
Lisa Birnbach describes it as "the wardrobes backbone."  Nothing is more preppy than the blue blazer, crested is optional.....enough said.
J Press $555.00 




The Wellie
LL Bean Boots will always be a favorite, yet sometimes a good rain boot is all that's needed, such as the Wellies.  If they were good enough for the Duke of Wellington, then they're good enough for anybody.  Farmandcountrysupplies.co.uk $54.00









P3 Tortoise shell 
The P 3 model frames are as classic as it comes.  Everyone wore them in the 60s.  They must be the horn-rimmed, tortoise shell type or one runs the risk of looking like Roy Orbison...very un-prep.
bensilver.com $375.00