Preppy in the 90s


1999 – A professional headshot of me taken by a photographer in Tribecca when my wife and I were living in New York City.  I took my glasses off for this shot because the lenses, as I recall, didn’t have an anti-reflective coating, and because the photographer was going for more of an intense lawyerly look.  I have on a Ralph Lauren navy blue wool suit with gray chalk stripes that I bought for $50.00 at a thrift store in Asheville, NC.  It was memorable because, though a great suit, it was one of the most expensive thrift purchases I’ve ever made, but I still wear it occasionally.  I’m not sure where I got the button down shirt and foulard tie.  Both were likely thrifted.


1999 – My beautiful wife and I on our wedding day outside her aunt and uncle’s house.  They hosted the reception.  I have on a charcoal gray suit with suspenders, a paisley tie with navy background and a white button down shirt.


1999 – Outside the small Episcopal chapel where our wedding ceremony was held in Greenville, SC.  I think my wife looks lovely here!  Opting for simplicity, we kept the invitation list to 50 and had no groom’s men or bride’s maids, just a priest, a crucifer and musicians.  We designed and printed our wedding announcement and program for the ceremony and asked that there be no gifts (though this was largely ignored).  We tried!

The coup in the do-it-yourself approach was my wife’s wedding dress.  While we were in New York, she selected her own material from a shop in the Garment District and took it to a boutique in Williamsburg, Brooklyn.  She asked them to design a party dress, which cut the cost down considerably.  The cap toe dress shoes I’m wearing with the charcoal gray suit were polished, but cracked, and had a small hole on one of the soles – likely visible to our guests when we knelt at the altar.

We’ve been happily married for 13 years.  As we look back on the wedding, we’re glad that we kept it a simple ceremony.  The organist was wonderful.  There were solos from a friend who was a professional opera singer.  A string quartet of classically trained musicians, my wife’s friends since childhood, played for us.  It couldn’t have been a more prefect day.


1998 – My wife-to-be and I on the balcony of a friend’s apartment in New York City.  You can’t tell here, but we were on the 44th floor high above 9th Avenue near Times Square.  We had been invited to a Christmas party.  I have on a wool houndstooth sport coat, a sage turtleneck and a pair of khaki pants.  My wife is wearing a vintage (60s) green and black houndstooth jacket whose design was very Sherlock Holmes.  That was a thrift find at Anne Merchant’s Time Warp shop (now out of buisness) in Greenville, SC.  I still have that jacket, too.

Middleburg_19931993 – With friends in Upperville, VA after the fall Piedmont Hunt Point-To-Point races.  I’m wearing a light windbreaker, a classic Norwegian Fisherman’s Sweater from L.L. Bean, a pair of rumpled khakis – rumpled being their usual state – and Bean Boots.  Among my friends is a sampling of Barbour, Burberry and Brooks Brothers.

Über Preppy Band – Vampire Weekend

Vampire Weekend’s 2008 song M79 references bleeding madras: “No excuse to be so callous/Dress yourself in bleeding madras/Charm your way across the Khyber Pass….”  Madras, a lightweight cotton weave usually with a plaid pattern,  is perhaps the most versatile and definitively preppy article of clothing, used for jackets, shorts, pants, shirts and even ties.  On Labor Day, I put away all my madras clothes (and seersucker/poplin) for use next summer.  However, now that it’s October in New York City and still hot (80s all week), I’ve been tempted to bend the sartorial rules a bit and  break out a madras shirt today.

In early madras shirts and pants, the dyes used were not stable and literally bled during washing, yielding slightly different hues that faded with time.  Jackets and ties that had to be dry cleaned maintained their vibrant color.  Below is a vintage (1960s) Gitman Brothers bleeding madras shirt.  The bleeding variety is harder to find these days, as most dyes are stable.  I rarely see madras in thrift stores. Vintage shops are your best bet to find the real deal.  If  you come across a madras piece you like that fits, don’t second guess yourself.  Buy it.  It won’t be on the rack when you come back.

Vintage Gitman Brothers Bleeding Madras Shirt

Vampire Weekend Lead Vocalist Ezra Koenig In A Madras Plaid Shirt

Here is a blast from the past – a shot of me in my college dorm in an actual bleeding madras button down shirt from Gitman Brothers, which I had for years.  I’m also wearing cotton shorts – most likely from Brooks Brothers – and a nautical belt (sailboat motif).   For more on madras, you might want to check out this post from Ivy Style.

For more about Vampire Weekend and the preppy connection, check out this article from Billboard.