In Which Coolness Is In The Eye of The Beholder

The latest entry in our Adolescence series bring fashion to the fore. Read on for lurid tales of high style from a legendary park avenue outpost…


Part One (Rebecca Wiener) Part Two (John Gruen)

Part Three (Tess Lynch) Part Four (Jessica Grose)

Part Five (Molly Young) Part Six (Lucas Stangl)

Part Seven (Andrew Zornoza) Part Eight (Rachel B. Glaser)

Part Nine (Andrew Lasken) Part Ten (Kevin Porter)

Part Eleven (Jamie Galen)

Part Twelve

The Ostentation of Riches

by Anna Dever-Scanlon

skaters, large pants, smoking blunts & my stepbrother collecting all of the smiths albums, nirvana, skate shoes, snowboarding, manic panic.

stop. enter prep school. the cool kids are wearing brooks brothers. the cool kids are wearing brooks brothers. and lily pulitzer dresses. and boat shoes.

am i crazy? lacrosse sticks and white baseball hats. tennis rackets. hockey sticks. sweatshirts and polar fleeces.

the author with her gfs

everyone was smart, some people just didn’t show it. and they were the cool kids. screaming “deez nuts” at each other as they walked out of the dining hall. it was healthy.

and then there were the kids who had some semblance of cool – who knew at least what other kids our age were doing (these people were generally from california and developed huge drug problems during long weekends shut inside their dorms.) also healthy.

so how does one deal with this? by becoming friends with the various weirdos that also found themselves in this strange environment. day students (i was one) were always good for this.

western mass

it is one of the ironies of the park avenue outpost i attended that it happens to be located in western massachusetts, home to a large amount of aging hippies who moved there to get back to the land in the sixties and seventies.also, theater kids, and the small amount of unabashed intellectuals who weren’t good at sports but had a certain gawky swagger about them that somewhat fit in among the heavy wood panelled halls and corridors.

i want to give you wedding rings

i was in every play and dated those intellectual guys and my friends were all the “artsy” girls in my class. it was tolerable.

the dress code at my dear old alma mater:

boys had to wear blazers, ties, and dress pants or khakis (so many khakis). girls had to wear dress pants or skirts or dresses. no jeans were allowed and if you were wearing corduroys or khakis you were supposed to wear a blazer.

no one did this, but occasionally you’d have a cranky teacher decide to enforce the letter of the law and make a girl go back to her dorm and get a blazer.

the de facto dress code for girls was lilly pulitzer dress, cable sweater, and kitten heeled mules. just like their moms. and they didn’t seem to care that they were clones of their parents. this lack of rebellion was the eeriest part of the whole experience for me. didn’t anyone want to even attempt to break away from what their parents were? apparently not.

conformity in dress is one of the main ways of communicating your acceptance of the status quo. maybe it is a class issue – if you have a lot to lose, you are more hesitant to rebel. or maybe it was just the nature of the boarding school atmosphere – when you are totally isolated, if you don’t fit in, you have nowhere else to go.

the author with a bf

some of the guys kept it fresh by wearing brightly hued shirts – pink, yellow, sometimes two at the same time. there is a certain art in mastering preppy style. pairing the perfect leather elbow patch tweed blazer with the perfect pair of navy lacoste pants and perfectly weathered car shoes.

my teenage mind was too turbulent to be able to sit back and enjoy it for what it was, although now i have a sort of nostalgic fetish for the classic preppy look, although always from a distance. it’s not something i want first hand contact with.

“Trouble Sleeping” — Corinne Bailey Rae (mp3)

“Like a Star” — Corinne Bailey Rae (mp3)

“Seasons Change” — Corinne Bailey Rae (mp3)

in a way, learning preppy style is like learning latin. it may be a dead language, but it forms the basis for everything else. it will always be there as a reference for american fashion.

it’s so entrenched and its forms are so rigid that there will always be a mischievous glee in breaking down those forms, mixing them up, and creating something new.

so, thank you boarding school, for taking a little grungy kid with an attitude and teaching her the staid backbone of american sportswear. among other things.

Anna Dever-Scanlon is a writer and designer living in New York. Her blog is Lipstick Dipschitz. You can view her clothing at Annamatrona Clothes.


Refinery 29.

Brooklyn Indie Market.


Mod Cloth.

In the Bag

Kim Weinstein’s site.

Who What Wear


Face Hunter.

Hable Construction.


Duh, The Sartorialist.

Business of Fashion.


We believed in Alice in Wonderland.

Jess vs. Wes Anderson.

Brian discusses Donald Barthelme.

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