‘True Prep’ Swag Bag Giveaway!

UPDATE: The contest is now closed. Thanks for the outstanding responses and great stories of your favorite preppy moments!  We’ll have a winner announced shortly.

Off the Cuff is happy to announce that it’s partnering with TRUE PREP to give away a great swag bag full of old school accessories for guys and gals.  The centerpiece is your own copy of the just-released ‘TRUE PREP’, by Lisa Birnbach.

This outstanding gift bag is made possible by the generosity of some equally outstanding brands: Vineyard Vines, L.L. Bean Signature, Cole Haan, Tommy Hilfinger, Kockaround Sunglasses and Jewelry for a Cause.

And before I forget, make sure to check out Lisa’s appearance on yesterday’s The Colbert Report.  As Stephen, said, he is the man he is today because of TOPH. Colbert the actor is also enshrined in the official Prep Pantheon.

So, on with the Swag Bag Giveaway!  To win this great collection of fun Ivy League merch, please tell us:

What is the best preppy moment of your life?

I can’t prevent anyone from making up a story, though of course I’d prefer you didn’t. Be honest, be detailed and have fun.  Get your response in (just leave it as a comment) by midnight, Wednesday, September 22 (NOW ENDED).  I’ll announce a winner the following Monday and this preppy swag will be sent right to their door. Domestic US delivery included.

Let’s hear about your best preppy moment ever!

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  1. Ok, honestly my best preppy moment has to go back to high school! I was sooo into Tommy Hilfiger. I remember dressing down from head to toe in Tommy Hilfiger (even the yellow and black tennis shoes!). I think I kind of miss those PREPPY times!

    Thanks for the throw back memory!

  2. Brendan O'Connell

    Truthfully, it has to be when I was born and my parents named me “Brendan Matthew O’Connell”. Yep, my initials are BMOC!! Set the tone for a wonderful gin and tonic soaked life of pink and green wonderfulness 🙂

  3. Robert Carrasco

    Although it was some time ago, the absolute best preppy moment was my first year of college in California, when a classmate from Connecticut saw my penny loafers, jeans, oxford shirt and crew neck sweater among all ofthe shorts and flip flops and said “you remind me of home!” and proceeded to nickname me “Biff.” I should look her up . . .

  4. Andrew Y

    Would have to be the time my little sister was getting sailing lessons at the local yacht club. I’m from deep southern Maine, which is full to overflowing with rich, liberal old people and their ultra-preppy offspring. I immediately dressed to the nines when I heard that I’d finally be getting into the fabled yacht club, putting together my Ray-Bans, best chinos, dock shoes, and what I think was a Tommy Hilfiger polo (complete with “surprise” collar), perfectly coiffed hair, etc. I pulled into the parking lot shaking in anticipation, totally ready for my big debut. When I entered, I saw a big empty room that looked like it had been thrown together over a weekend with a few trophies on the opposite wall. Huge windows overlooked the harbor, but otherwise the place was completely barren. No pillars or marble anywhere. A bored girl sat on a folding chair, wearing standard high school American Eagle summer fare. She nodded at the window and said my sister would be in soon. When the other parents traipsed in, they were all in various states of disheveledness.

    A tear still comes to my eye when I think about it. One of my greatest outfits and most prepared attitudes. Shut down by reality. My sister got told she had a really cool Dad for the rest of the summer, so it wasn’t all for naught.

  5. Angelina

    This is probably more of a lack-of-prep story, but years ago when I was a kid, everyone in my class at school was getting ready for cotillion, except for me – my parents were from immigrant families and didn’t quite get the whole thing. I begged and pleaded, because nobody likes being the odd kid out, but no dice. Fast forward to present day, and I’m talking about how I’ll never be invited to fancy work dinners because of my habit of immediately dumping my fork contents down my shirts. My father remarks that it’s a shame they didn’t have classes in those things when I was a child. I mention cotillion. “THAT’S what that was?” he asked, aghast. “Why didn’t we sign you up?” He’s still appalled. Granted, my friends say it was more about itchy tights and sweaty palms, but the look on my father’s face was priceless.

  6. Percy Chatsworth

    Spending the many weekends/weeks at the cottage of an established Toronto artist I dated. We would hop around to other cottages around the area to visit friends – Steaks and G&T dinners with members of the Order of Canada, many bottles of wine with Canada’s wild fashion czarina, Spending an afternoon with a top Canadian financier and his girlfriend, as they were completely blitzed off some marijuana (And possibly more). Essentially, I was running away from my family to spend the summer with Toronto’s ‘top’ people, seeing them behind the curtain of their Toronto lives in Canada’s Muskoka Lake, our Hamptons.

  7. I was up at a friend’s cottage about a month ago and we were going out for an evening boat ride. There were a bunch of people there I’d just met for the first time, so they were unaccustomed to the way I dress. I stepped onto the dock wearing a navy V-neck with an orange polo underneath, khakis, and navy boat shoes. One of the girls shouted, “Whoa, hello J.Crew!”, to which I replied, “Actually, this sweater *is* from J.Crew.”

  8. Reagan’s in the White House. I’m a sophomore at Georgetown University’s School of Foreign Service. As is customary, my sophomore seminar concludes with a cocktail at Dean Putnam Ebinger’s townhouse. I hoof it on foot from my dormroom with my classmates dressed in a seersucker from Jos. Banks on 18th and L, Sperry canvas boats, and tortoise wayfarers. It is spring semester in the Eighties after all. By the end of the evening I am one gin and tonic too many and walking into the Dean’s well adorned, linen covered walls. I pull it together enough to lead the entire class in a rousing chorus of Monty Python’s Philosopher Song:

    Emmanuel Kant was a real pissant who was very rarely stable/ Heidegger Heidegger was a boozy beggar who could drink you under the table/ David Hume could outconsume Willhelm Freidrich Hegel/ And Wittgenstein was a beery swine who was just a sloshed as Schlegel.

    Got an A. Minus.

  9. Ray

    Voted “preppiest” at my High School in 1980. The fact that my school featured preppiest along with best looking, most popular, etc speaks volumes about the kind of school it was.

  10. William Burdick

    This story is not about gin and tonics, sailing in Cape Cod, or Reagan’s presidency. It is about green pants. On one lazy summer day, I ventured down to our city’s Celtic festival. Feeling, well, festive, I decided to wear my green chinos in celebration of all things Irish. The day was a relaxing one, complete with mediocre fish and chips, stout beer and botched Gaelic. Of all the booths and stalls in the festival, one especially piqued my interest – the kilt stall.
    This kilt stall was unlike any other. There were no tartan plaids or emerald greens to be had – there was a sea of khaki. Khaki kilts with cargo pockets. Like wearing penny loafers with socks, some things just don’t mix. Half amazed and half disgusted, I gandered inside. Sure enough, a hairless man, who appeared to be the stall’s sole proprietor, was proudly sporting a “utilikilt.” I looked at him. He looked at me. And then at my green pants. And grimaced. I couldn’t help but laugh.

  11. Martin

    One day during my sophomore year at Georgetown University, I went to class sporting my navy and red striped bow tie, along with my favorite chinos, a white and blue university stripe oxford, navy blazer, and penny loafers. While strolling through campus, I spotted a bow tie-clad professor across the front lawn, and he spotted me. We acknowledged each others’ presence, as if we were part of some sort of bow tie-wearing fraternity. As we approached, he jokingly said to me, “Hey, you’re stealing my thunder right now,” to which I replied, “We’ve got to stick together, my brother.”

  12. ALM

    I didn’t come from a preppy family and had never dressed like one before; but when I was 16, I was invited to my best friends sisters confirmation. Having just gotten my hands on a copy of The Official Preppy Handbook, I somehow convinced my parents let me wear a seersucker. Not coming from a preppy town, i was told that I would stand out. And stand out I did, amidst the blue blazers and dark suits. When I walked into the church, in my seersucker suit, white linen shirt, and fantastically colored bow tie, people couldn’t help but smile and ask about it. Afterwords at the party I was happy looking in seersucker that more than one girl came over and asked me to dance.

  13. Cary

    I was at a nightclub recently, awash in a sea of printed t-shirts, gelled, spiked hair, ripped jeans, mini-dresses, and of course a lot of black. Two girls talking near me, about me:
    Girl #1: “Wow, that guy looks too nice for this place.”
    Girl #2: “Yeah, he looks like he has a steady job.”
    Later in the night from some random guy: “Dude. You have got to be the CEO of something.”

    I couldn’t have looked more preppy (and out of place) at the time due to my typical uniform – penny loafers, khakis, and a blue stripe OCBD. My standard attire since reading the Offical Preppy Handbook at age 13.

  14. SB

    At a wedding this summer, a good friend of mine decided that our sartorial choices for the wedding should reflect the geographical region of the country where we were raised. Having grown up in the northeast, I wore a trim pair of khakis, a blue/white striped oxford, a burgundy/navy repp stripe tie, penny loafers, and a navy blazer. I was a little embarrassed for my friend when he showed up in an ill-fitting white seersucker suit and white shirt, which he felt was appropriate for a southern gentleman.

  15. Carly C

    When I was in 5th grade, my family moved to Honolulu, HI for my dad’s job. Completely out of my element, I remember school shopping to be quite an experience. Over the summer, I insisted that my wardrobe be purchased exclusively at Liberty House, a local department store, because it was the only place to find Ralph Lauren childrens clothing. I showed up on the first day of school in what apparently, the other kids (decked out in Quicksilver and the like) thought to be a uniform. One of the girls in my class came up to me and whispered “We don’t have to wear uniforms here. Not until high school.” I think the rest of my classmates were more embarrassed for me than I was for myself. I’d never been so proud to stick out.

  16. Sam

    A few years back I was a visiting professor at a reatively small and working class background college. We were encouraged to dress “professionally” and I (with a limited wardrobe and limited budget) did my best. During the winter I rotated between a camel hair and a tweed herringbone jacket almost every other day, along with khakis, oxford cloth shirts, crewneck sweaters, and a hand full of repp ties. Shoes were loafers, bucks, and/or a pair of old, dark green, suede Adidas Stan Smiths, which I wore more often when I learned what “professional” meant to the others.
    I got many, often sarcastic, comments about the frequency with which I paired the jackets with the suede tennis shoes. But one day I was complemented by an attractive, cool, young art student who told me that I reminded her of “a character from a Wes Anderson movie.” “You know,” she said, “old school preppy.”

  17. Matt

    My friends and I had gone into a bar, and were playing a game of beruit after coming from watching an afternoon tournament lacrosse game. Me (Northeast MA Prep school) my friends (Rival NH prep school of same name) each have on colored shorts, an OCBD and a D-ring belt. While my friend sports sperry’s, I was more comfortable in my penny loafers. As we are playing, this group comes up to us and wants to learn how to play. We explained that while it was going to take a lot for an team from our respective prep schools to play together, but we taught the group since they were interested. As the game progresses, many of the onlookers (members of the same group) begin to cheer for us as we are playing well, and one exclaims to his friends you guys are getting smoked by “TEAM Brooks Brothers!” even though not one of us was wearing anything BB. We were honored, however and toasted a highball with the team we played against right after. We were proud our prep colors were on display that day.

  18. Christine Z.

    I went for a job interview wearing a white blouse partly open over a striped seersucker dress with grosgrain ribbon trim. And I got the job –
    my first one out of college!

  19. Bryce C

    I was at the Kennedy Center this summer for an afternoon performance so I decided that it was the best time to bust out by best summer seersucker. I put on my J. Crew seersucker pants, white Ralph Lauren OCBD, Cole Haan bucks and a blue and green ribbon belt. I get there and immediately see a sea of badly dressed theatre-goers (fanny packs and and cargo shorts galore)! I slip into my seat and don’t really pay attention to the person next to me until seeing his white bucks. I immediately get excited to see another prep and start moving my way up and then I see that he is wearing seersucker pants, a blue and green ribbon belt and a white Ralph Lauren OCBD. I finally look at his face and he is beaming and then he says “Welcome to your future!” I am only 19 and he had to be at least 45 so I really got a kick out of it. It is fantastic to see that preppy staples will last a lifetime and will always be a timeless, elegant look, no matter how old you are.

  20. Wehaf

    I spent a summer taking courses at Johns Hopkins, during which they held the lacrosse championships there. My friends and I would put on our polo shirts and go and watch lacrosse. Does it get any preppier than that?

  21. Phil Berkowitz

    I attended a family event not too long ago. After everyone commented on how nice my two sons (aged 9 and 12) looked, I took another look and started to laugh. I realized that they were dressed in True Prep from head to toe. Both were dressed in khakis – the little one wore a white Brooks Brothers OCBD and a Vineyard Vines blue tie (with soccer balls on it) and brown shoes; the older wore a french blue Brooks straight collar shirt, a yellow Vineyard Vines tie (with blue sailboats on it), a blue blazer, and brown shoes. I couldn’t look as preppie if I tried (although the True Prep’ Swag Bag might help).

  22. Jack A. Mallon

    I’m a second year history student at the University of Guelph and last week, seeing as it was the first week of classes, I wanted to make a good impression. Dawning my father’s tweed blazer from his days at Guelph with the University crest and elbow patches, as well as khakis, a blue oxford, and a rep tie I set off for campus, bringing my squash racquet with me for a game later that day. Upon reaching my Ancient History class about ten minutes late I strolled in, hoping not to interrupt my professor. As fate would have it I had been taught Latin by the professor several times, and when he saw me, halted his lecture and greeted me in Latin and started telling me how squash was his favorite sport and that he’d like to play me sometime. Glad to have avoided making a bad impression with my tardiness I took a seat for the remainder of the lecture. After class as I was walking down the hall I was approached by three or four students asking me a multitude of questions about the course. It turned out that my friendliness with the professor and my overall appearance had led them to believe that I was the assistant professor. I played along and answered as many questions as possible. People can say what they wish about preppy attire, but for me it is the embodiment of dressing for success.

  23. AEV

    Great meeting you last night in G’Town at the VVines event – and, as usual, a great post. My “best preppy moment”?

    That’s an easy one: Arguing – and winning – with my boss about why I shouldn’t have to wear socks with loafers at the office during the summer (assuming no formal business meetings are on tap) and why it’s “ok” that I wear brightly colored ones during the cool/cold months. He got a free style lesson or two, I got to wear my loafers with no socks. We both won.

  24. Jeremy

    Since we’re talking about clothing, I’ll off up one of the most ridiculous moments I’ve had. Several years ago after getting back from the Virginia Gold Cup I went straight over to the apartment of a friend who was having a party. After an hour so of chatting another friend who hadn’t been at the race walked in. I was stunned for second and then walked over to him announcing “At least someone got the memo!” It turns out we had, entirely independently, decided on an outfit of white shirt, blue blazer, bow tie, and green oxford pants. These things just happen.

    I’ll see if I can give the full effect with a picture here:

  25. Dave

    Well there really isn’t one specific moment, but rather a series of times,. Like the first time getting intoxicated with a friend of mine, emptying his parents liqour cabinet and drinking his father self concocted brew of liquors left after a party and strained through an opera sock, to summer at said friend’s grandmother’s house in Pine Orchard. Or perhaps my vehicles which, until I could not find anymore, were adorned with my initals in nautical flags, and going to the Cape in the back of my relatives woody station wagon back in the eighties. But a couple of memories do stick out, being the 17th man on America3 back in the 1995 Cup trials. But I would have to say the most would be back in college. I was invited to a debate watch party in 1988. The famous “You’re no Jack Kennedy” debate, wearing a bow tie, self tied of course, a tweed cardigan, jeans and penny loafers in amongst all the Dems, including Teddy Kennedy himself, all decked out like psuedo cowboys, that perhaps might bring the fondest memory to mind.

  26. When my mom gave me my grandmothers pearls. My family is from the north and not traditionally very preppy. But when my mom saw that I was becoming a prep she knew how important pearls are to that. So she gave me her moms pearls. Thats my preppiest moment this far

  27. Cartwright

    My boyfriend and I went to a wedding decked out in full seersucker. Seersucker suit with bowtie and loafers with no socks for the man. Hand tailored seersucker strapless dress with a multi-colored seersucker sash for me. Made the bridge and groom look like chumps.

  28. Will

    As I look back on my 15 years of life and reminisce on the good the bad and the ugly in terms of dress, there is but one moment that particularly affected my preppy style as well as values. It wasn’t the time I ran into the then candidate Barack Obama in Hawaii decked out in a tucked in well fitted polo and some great khaki shorts, nor was it when I found my father’s old Brown University sweatshirt worn to pieces and my mother’s vintage cricket sweater in the same day. Rather, it was an unexpected time and place where my moment occurred. My family and I go to church every weekend in our suburb outside of Washington, DC. Of course it is a prep filled church full of bow-ties and shorts with critters matching to Lilly Pulitzer dresses and Jack Rogers sandals. That day, in between eyeing one man’s outfit of sock-less Gucci loafers and nantucket red trousers, I saw another man across the room sitting with his family. I was aware that the son of Eunice Shriver Kennedy shriver and his family attended mass at the same church as we did, and always saw them to be very pleasant people. However, that day the man joining them was Sargeant Shriver, who hadn’t been present at Mass for quite a while. This was just after his wife Eunice had died and within reason he had been recovering from that tragedy. However, a man of his character cannot just arrive at church in his sweats and a t-shirt. Even though he had been absent from a few recent masses, he was wearing a blue blazer, well worn and frayed khakis, and great repp tie that must’ve been a good friend to him for longer than I have been alive. Nothing kept him from looking sharp when he showed up to church. On his lap was his grandson who he held close as he watched his first mass since he had lost his wife, and I realized the significance of this moment.

    This memory had been put away for a while, and Sargeant Shriver appeared at mass more frequently since then. Although the man and his legacy will always be something attributed with him, that day it wasn’t his past feats that appealed to me. Rather, it was how strong he was in mass on that particular day. It took me a while to process how much heart it must’ve taken for him to continue on in the midst of tragedy. That is the true essence of the preppy lifestyle. Of course when somebody calls you preppy, they are referring to your style of dress, but it will always have a different meaning for me. That moment truly shaped how I look at preppy today.

  29. Randolph and Mortimer

    Realizing at first read that TOPH was a satire of my particular tribe, and that if being prep is to be resolutely low key, that writing a comment about ones self on a “web-log” with the hope of winning a prize is the least prep thing of all.

    The other comments are a great read, though!

  30. Haspel

    Best prep moment ever ? Easy , four years at Ole Miss . Second best prep moment , Living up to an old Ole Miss joke ” How many Ole Miss students does it take to change a flat tire ? Three , one to change the flat and two to mix drinks .”

  31. Nicholas

    My best prep moment would have to be during the first week of law school when I wanted to make it clear who I was and what I was there to accomplish. In the course of that first week, I had at some point wore an orange paisley bowtie, madras pants, lime green slacks, and nantucket reds – all paired with the perfect pairs of sperry’s.
    The pros of doing this is that all of the southern girls at my school were instantly my new friends, and only the most respectable guys were in my study group. It’s always nice to have professors commenting on your dapper and unique look, with the added perk of finding the perfect southern belle to settle down with.

  32. Best prep moment.. or rather the time I truly felt like a character in TOPH, was driving through Middleburg, VA in the fall a few years ago. I had just left the VA Gold Cup with my parents after my eighteenth birthday and we were on the way to pick up my most anticipated present… my first bowtie from Southern Proper. I still have it today and it remains one of my all time favorites.

    In fact, this summer I started “Bowties Wednesdays” at my internship, and even got the Managing Partner to participate!

  33. BenR

    I went to Yale for undergrad. My friend, who I haven’t seen in a long time, visited the campus last week.

    He posts on facebook:
    “Dress code at Yale is apparently Andy Bernard style”

    I think to myself, Yalies don’t dress like Andy Bernard!

    Then I look down at myself. . . Blue Blazer, Khaki Pants, Pink Oxford . . . and I realize I’m dressed like Andy Bernard! PML (Prep My Life)

  34. Drew

    In May, a few weeks after our first son was born, he was gifted with his very first Polo and pair of boat shoes – the very same color and pair I was wearing that day! Glad to know our friends care about my son’s upbringing as much as I do!

  35. Greg

    My best prep moment, was in high school when everyone was going through this hazy 80’s dress and discord, while I was reliving how my Dad dressed and behaved during the turbulent 60’s. One day I arrived on campus in a bright pink oxford button down shirt, bermuda shorts(this was the beginning of April–still a little chilly) and my Bass Weejuns were so worn down–that I wrapped duck tape around them, just to keep them in place. Well, this set off a maelstrom at school, first breaking the rules by wearing shorts and my beat up penney loafers did not go over well. Let’s just say, I was the talk of the yard for a few days. But, I never relented in my preppiness, only as an adult, I’ve gotten better with my fit and fabric choices.

  36. Zack

    My best prep moment is probablly going on right now! i mean i wear white nike socks with sperrys, the shorter shorts and bright shirts with my Ray bans!

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