Alison: Return of the Preppy

For some, fall means crisp air, red leaves, and acorns leaving dents on your car hood. For others, it’s the weekly morning keg party in a parking lot outside of a football stadium. To me, however, fall means my return to preppiness. 

For many years for many Americans, there was nothing quite like cool Saturday afternoon in the bleachers sipping Jack and Coke from a stadium cup and wearing a cableknit sweater to keep warm. This pastime, enjoyed by so many 20-somethings for nearly a century, has given way to more modern endeavors (watching 15 different football games on your satellite feed from the comfort of your own home, going to school in sunny California to escape said fall weather, and the advent of fleece, for starters), but something still feels right about it to me. 

The heritage textiles, the layers, the basset hounds… Tommy Hilfiger’s ‘Ultimate Tailgate’

With the release of True Prep, the follow up to the 1980 classic The Official Preppy Handbook; the recent rebirth of the Tommy Hilfiger brand under Peter Som; and the rampant collegiate trends, it seems like “preppy” is back with a vengeance. 

Often the preppy look is written off as lacking intrigue, boring, or downright dowdy. Many women like to think that “preppy” is incompatible with “chic”. But what about Jacqueline Kennedy Onassis, Grace Kelly and Katherine Hepburn? Do Tory Burch, Michelle Obama and Gwyneth Paltrow mean nothing to you? And while it has treaded into much trendier waters, have you no respect for the humble origins of our beloved J. Crew? My dear women, “preppy” can indeed be compatible with “chic,” you just need to learn that preppy doesn’t only mean embroidered ducks on your corduroys or a pair of reds from Murray’s Toggery.

Navy Schoolboy Blazer (J. Crew, $188)

As classic as it gets, this is a preppy style will always look good (granted decent tailoring and fit). My little brother had to wear one at school from 6th grade on, so for a while I was all about the hand-me-up, children’s-sized (read: 3/4 sleeves) navy wool blazer. With the big gold buttons, this one is a dead ringer to Ben’s Brooks Brothers school uniform, and a must buy. Wear with just about anything. Seriously.

Leather Blucher Moc (LL Bean, $69)

 The menswear look for shoes has been big for the last couple seasons, but I can’t tell you how much I detest the look of oxfords. While yachting loafers just generally sound repulsive, too, these classic bluchers from LL Bean are a wonderful alternative. I can’t tell you how comfortable they are, and they have a wonderfully nostalgic feel. I love mine with a cropped pair of skinny jeans and a long cardigan. They are a men’s style, but heck, that’s what preppy is all about: stealing the best from the boys.

Ladies Winter Force Waxed Parka (Barbour, $399)

Barbour coats are the staple of fall where I hail from, no matter how stylish (or not) they are. This one, however, is a timely take on the classic wax field jacket. Hello military trend.

Boys Cotton Roll-Neck Sweater (Ralph Lauren, on sale for $49.99)

The quintessential preppy look involves major layering, and what better to layer with than a comfy sweater? The pop of red will work wonders with the rest of your fall wardrobe, and the boys sizing means it’s a bit more affordable.

So go on with your bad self and pair some of these preppy staples with your modern, stylish wardrobe. You’ll look like the million bucks your great grandaddy donated to Harvard.



  1. love prep says:

    But this post seemed a little bit phoning it in to me. J. Crew and LL Bean? Those are pretty standard around DC. If you look around the city, you would clearly surmise that preppy never left, so how could it be “returning.” My style is pretty preppy, but about a quarter of my wardrobe already comes from J Crew… I would have loved this post to showcase an unsung designer, up and comer, or a cool look from a designer that doesn't usually skew preppy.

    September 30, 2010/Reply
  2. Anon says:

    I like your writing style, Alison! More designers/stores/options would be nice, but I am in love with the J. Crew blazer!

    September 30, 2010/Reply
  3. Allison says:

    Great post, but I was looking forward to seeing how you integrate preppy and chic. I wholeheartedly agree that the two go hand-in-hand; Lilly Pulitzer and Vineyard Vines are only one aspect of “preppy” wear… an aspect that should be buried alive. Obviously J. Crew falls into this category, as well as LL Bean Signature and Land's End Canvas. You can even find some great buys at Loft, Banana Republic (I know, I know) and boutiques in the DC area.

    September 30, 2010/Reply
  4. Cat says:

    I couldn't agree more!

    September 30, 2010/Reply
  5. Andrea says:

    That JCrew schoolboy blazer has been on my To-Buy list for a while, so I think this is a sign I should just buy it already.

    Maybe I am missing something, but what's wrong with Banana Republic?

    September 30, 2010/Reply
  6. D says:

    Was there supposed to be more to this post? It just cuts off abruptly at the picture of the shoes…

    September 30, 2010/Reply
  7. Christine says:

    What do you look for when you buy children's cut clothing? I've often thought of doing it myself, for price reasons, but would probably do it online…

    Do you check length, etc? Also, do they tend to fit differently? And is it better to buy boys' clothing than girls' ?

    October 1, 2010/Reply
  8. LL says:

    Love it! Can't wait to let my prep flag fly this fall

    October 2, 2010/Reply