Tag Archives: preppy topsiders

Another ‘How to be Preppy Guide’

Hello and a good day to all… we hope you are able to get out and enjoy it. Or stay in and enjoy it, whatever your preference.
Today we bring you another example of the as-yet-to-be-named viral infection sweeping Manhattan. Likely an airborne virus, this mutant strain appears to take over writers’  and editors’ thought processes, frequently resulting in columns on “How to Be Preppy.”  Our latest example comes via this column at website Complex, a site TP visits every now and again for research purposes only. Honest.
Band of Outsiders

Band of Outsiders

In explaining how one accomplishes Prepdom (our word), Complex awards Band of Outsiders its designation as “The Brand,” presumably “the” preppy brand.  Above we show the apparel and accessories illustrating Band of Outsiders’ designation as “The Brand”: their trenchcoat in a Blackwatch plaid, accented by the ‘trapper hat’ trimmed with raccoon. Below, our selection of this look with David Beckham in the company’s cashmere tartan sweater vest.
Band of Outsiders Cashmere Sweater Vest

Band of Outsiders Cashmere Sweater Vest

The rapid spread of the virus shows no signs of abating; we hear it is frantically being tracked by the CDDC (Centers for Design Disease Control) in an effort to maintain some, any sartorial standards. Below, our selection of Penn Badgely in a Band of Outsiders’ blazer and grosgrain wrapped loafers, from GQ’s August issue.
GQ August 2008

GQ August 2008

Many readers not ‘sur intime avec’ Band of Outsiders may remember them for their collection with Sperry Topsiders that debuted this past spring, the company’s first collaboration with an outside entity.
But we digress. The Complex Guide continues with pointers on ‘The Drink‘ (a Hendrick’s Gimlet)…

… as well as The Tie and The Shop (if you recognize the photo below, please award yourself ten extra Preppy Style Points, a currency we regret to inform you that is utterly without foundation or value, other than our holding you in the highest of esteem).

Now, you know exactly where this is going: The Shoe (of course), The Restaurant (appropriately situated on the UES,) and more. We must stop at this point to provide readers with full disclosure: we actually adore much of what Complex publishes, and quite love this little treatise as well, so there, our secret is out. We hope you don’t think less of us.

Until next time….


Filed under Logos, preppy, Preppy clothing & brands, Preppy Fashion, preppy lifestyle, Preppy People

Preppy Nautical Goodies: Sperry Topsiders, Figawi & Regatta Pillows

Preppy Shoes Sperry Topsiders Green

Warmer weather causes The Princess to drift off and dream about the water… and the beach… and sailing… and… well, you get the drift. When we saw these Topsiders, we thought they most definitely looked like they would be great for the boat. We were surprised to see that Sperry now offers a small clothing collection in addition to their splendid shoes. We kind of liked their Women’s Polo, perhaps in part because the logo is mercifully small. (It’s not our fault for being unaware of the clothing part of their offerings. Perhaps if their shoes were of poorer quality, they would require replacement sooner and we would have been looking at their website sooner!) We were very impressed with the Cotton Duffle, thinking that it might serve a myriad of purposes when it comes to summer travel, and trust The Princess, it is more than reasonably priced. A $29.99-kind-of-reasonable-pricepoint. That qualifies as completely and insanely priced, unless it is microscopically sized, and the description did not give the size. Hhhhhmmmm. Still, I would run, not walk to their website and decide for myself.

Sperry Women\'s Polo Shirt Navy Sperry Topsider Cotton Duffle

The men’s Striper Slip-on from Sperry (seen below) actually looks pretty good as well, although we did waffle for a moment or two… can’t say why for sure. Perhaps when viewing it in madras it just didn’t look right; madras is a great fabric but not right for all items or appropriate for all occasions. (There’s a topic calling for greater discussion, don’t you think?) What did look right to us for the guys was the Figawi Jacket; you can do some serious sailing in this. Oh yes indeedy. Which raises the question: why is it not available in Women’s sizing? Is the Princess supposed to buy it in a Men’s Small…hello? BTW, for those wondering what or who a Figawi is, it’s an absolutely outstanding event over Memorial Day weekend on the Cape. It’s the first big Regatta of the season, boats doing Hyannis to Nantucket on Saturday, Sunday is a massive clambake and then Monday back to Hyannis with a party after the race at Hyannis YC. It is simply a must. I think there’s a fundraiser the weekend before, also in Hyannis .

Men\'s Sperry Topsider Slip on Striper


Sperry Women\'s polo


All this talk about sailing and such reminds the Princess of one of her favorites: the Regatta Collection of pillows. These are some our favorites – bright nautical flags on an eggshell background, some with solid colors on the reverse side, many with contrasting piping for an elegant accent offsetting their whimsical motif. So if you can’t make it to Figawi, why not try these? If not for yourself, perhaps as a Hostess gift for your next visit to Skip & Octavia’s thsi summer? at

Regatta Pillow Collection at PreppyPrincess.com

Regatta Pillows Collection by PreppyPrincess.com



Filed under Prepalicious, preppy, Preppy Fashion, preppy lifestyle