Hit the road, Jacks.

Skateboarders were, for a long time, something like modern-day outlaws, getting into shenanigans wherever there was a rail to ride or a little old lady to scare.

A recent post on A Time To Get got me thinking about how "totally rad" this subculture is and how much more I want to learn about the sport and the people who have made it so gnarly (especially the girls because there are so few of us but especially the boys because they are so darn cute).

Skateboarding, surfing, and that whole California thing have, in the past fifty years or so, come to define the American youth. Think of Lords of Dogtown, the X Games, the Beach Boys. Tony Hawk on a box of Frosted Flakes.

The whole wide world has gone to the boards.

And for the past six months I have cruised all over New York City on my American-made Zig Zagger, put together by the pros at Autumn.

My deck (and my carefully honed ruffian persona) would be nothing without this dirty pair of Jack Purcells which have seen me through many long nights and epic rides. I may not be the fiercest hooligan on the street, but I know a good shred when I see one.

The Jacks look jaunty with shorts and fresh to death under a sun dress. Together these summer staples (skateboard and sneaks) have cruised seamlessly into fall, and keep my street cred alive and kicking. Or so I tell myself.

All pieces, from the selvedge shirt to the chambray frock, are by J. Crew.

A holiday on the Cape.

For two straight weeks I have seen nothing but rain and gloom from sea to fruited plain. Rather than crawl under the covers and hibernate, I prefer to recharge with photo reminders of this past summer.

On Labor Day weekend Kate, Liz, and I made our maiden voyage to Cape Cod. We spent a night on the Dennis shore and one by a pond in Chatham. While not the most action-packed vacation we had ever taken, we certainly snapped enough pictures to prove otherwise.

Back seat warriors like myself must head into battle fully prepared. I suited up for the drive in my favorite Nantucket Reds. The ancient, faded L.L. Bean Boat 'n Tote carried necessities (water, makeup, sand, and Gatsby) and, later, the crown.

My souvenirs must tell stories, and this crown is no exception. It began its journey in the back of an Altima and now hangs in my closet, patiently awaiting its next adventure.

This sticker was affixed to the Altima's rear right passenger window. I spent a lot of time staring at that flag between New York and Providence, R.I., where I took this photo, and, finally, the Cape.

On Saturday afternoon we walked along Route 6, the Cape's main drag, to Captain Frosty's for their famous lobster rolls and ice cream.

As we unpacked our duffels in Dennis, Liz said, "Cary, how many pairs of khakis do you have?"

"Did I pack or do I own?"

"Do you own."

I thought about it for a minute and then replied, "I really can't say."

You can never own too many khakis. I swear by J. Crew's Boyfriend and Original fits.

On Saturday evening we took the boat for some water-skiing and a tour of the Bay. I was allowed to drive until I plowed into a lobster buoy.

We spent nearly an hour strolling the beach, hoping to catch the sun as it sunk below the horizon. Our iPhones were poised and ready to capture it.

On Sunday morning we drove to a nature preserve on Nauset Bay to hike and hunt for shells. This nautilus now sits on my windowsill.

The nail polish is, as usual, "Kennebunk-Port" by OPI.

Our cottage in Chatham boasted enough bunk beds to fill a college dorm room and a hammock and this pretty view.

Our last Cape adventure before heading home was a long boozy brunch at Spanky's Clam Shack on the Hyannis harbor. The waitress praised this cerulean sip as Spanky's special recipe, but I'm pretty sure it was just a Bay Breeze. Paired with slaw, fried clams, and quahogs, it tasted like a dream.

In just 48 hours we snacked on some of the best eats of the New England shore while admiring its prettiest sunsets. Scargo Cafe and Wildgoose Tavern also hosted our hungry little crew.

My stash of khaki pants thanks our hosts for the wonderful vacation.

The great American manicure.

As a little girl I begged my mother to let me join her on her weekly trips to the manicurist. Cindy at Shar's beauty parlor would wrap Mom's nails in fiberglass, buff them with what looked like a mini jackhammer, and apply two thin coats of cotton candy pink. More often than not I wiled away these mornings spinning in the stylists' chairs, flipping through old Vogues, and stealing candy. But on a couple special occasions Mom gave her blessing, and I too had my nails "done". Cindy, like most pros, swore by OPI. A love affair was born.

Coney Island Cotton Candy

A sweet pink for a little lady who would grow up to be a big New Yorker.

OPI achieved nail salon ubiquity for their cheeky marketing, and most girls freely admit to falling victim to each season's clever names and collections which echo current fashion trends. This season, for example, the Matte and Suede Collections capitalize on the craze for flat, shine-free finishes.

Wild manicures are a good way to be in the moment without becoming a slave to trends, but I keep an old Topsider shoe box filled with favorites that look fresh season in and season out. In my permanent collection are classic colors with names that draw inspiration from great American locales (and a favorite Christmas carol).

Baby It's "Coal" Outside

Dark, moody hues have been trendy for so long that they now count as modern mainstays. I like this shade because it's softer than pitch black and more classic than hunter green or navy.

Big Apple Red

I first discovered this vermilion while interning at Ralph Lauren in (where else?) the Big Apple. Bright lollipop red was a favorite at 650 Madison.

Lincoln Park After Dark

This universal favorite kicked off the dark, almost-black phase in fall 2006. It looks especially seasonal against cream shades, winter whites, and my Hunter wellingtons.

Cajun Shrimp

This is the perfect warm weather hue. I love to wear it with pale blue chambray sundresses, thin yellow scarfs, white sandals, and a deep tan.

Kennebunk-Port

Meet the granddaddy of them all, the one that set the mani-pedi stars in my eyes and keeps summer at the tips of my toes all year 'round. I wear it so frequently that it has become something of a neutral shade for me.

A collection I'd love to see in the future would echo those dreary Missouri landscapes that I miss so much: moss and olive greens, khaki, dirt brown, gray as gloomy as the October sky, and bright holly red. But until that hits the stores, I'll stick with what I know and love.

For a comprehensive list of all OPI shades and collections, most of which are available to order, please visit Nail Polish Diva.

Pastoral and pigskin.

On Friday I ran along my old route in Columbia, Missouri, my college town. I ran west toward Scotts Boulevard, past the church and the golf course, past the playgrounds and the subdivisions, and stopped along a dirt road to take some photos.

Gray, gloomy skies don't make Missouri any less beautiful. This farmhouse, guarded by barbed wire and a thick wall of holly, looked especially proud against the clouds and strong cold breeze.

Ripe holly stood out against the greens and browns and grays. It also reminded me that Christmas is now just two months away.

If not for the rain I might have snuck past that fence for some close-up shots and fun-seeking, but menacing sprinkles demanded I make tracks.

My adventure outside the farm served as inspiration for Saturday's outfit at the Homecoming game. I channeled the sky and earth in white jeans, a white pointelle cotton tuxedo shirt, gold belt, brown leather handbag, and (of course!) the beloved olive drab fatigue jacket. All pieces are by J. Crew. On my feet are the peep-toe, heeled brogues by Nine West. The lipstick is Lancome L'Absolu Rouge in (just like the holly) Berry Noir.

Standing next to me (and equally well-dressed) is one of my oldest and dearest friends Kristen B., author of White Gloves and Party Manners. She wore a black Merino wool cape by Ann Taylor Loft and a beaded black and gold headband by Belle.

The old college try.

I'm spending the extended weekend in my Missouri college town, catching up with dear friends and remember what the rest of the country looks like in autumn. [See below for its beauty.]

Tonight we visited the Blue Note to catch Pete Yorn on his current tour.

His album musicforthemorningafter was the soundtrack to my senior year of high school. His new beats set the tone for my Brooklyn days and Manhattan nights. I think he's wonderful.

Yorn's is good American music: music created with guitars and drums and pianos. Music created for dancing and ruminating on fast-moving trains. Music for interstates. Music for heartbreak. They make me wish for a fire escape and a thick wool sweater and a wood-burning stove. These are epic songs for epic youth in an epic country.

Pete puts on a good show, too.

Mid-Best.

Autumn in New York is hailed as the City's prettiest season, and I do agree that cool breezes, choppy rivers, and long afternoons spent tossing the pigskin in Central Park give new meaning to the phrase "urban oasis". But to really discover what makes this season so special, to understand why the long winters and the hot summers are worth all our trouble and discomfort, you must leave Manhattan.

This week I am in my home state of Missouri, rediscovering an oft-overlooked part of America and reconnecting with college friends. My journey began in Saint Louis, where backyards like this are a dime a dozen and where long boulevards seem to burst into flame with Technicolor maple and sycamore leaves.

I could spend all afternoon tromping through these woods - found outside city limits in the village of Chesterfield - but not, perhaps, in these shoes. They are my current daytime favorites - vintage pony hair by the granddaddy of department stores Saks Fifth Avenue, scooped up at Williamsburg's Beacon's Closet.

L.L. Bean debuts its Signature Collection.

On Wednesday night I visited Hosfelt Gallery to celebrate the launch of L.L. Bean's Signature Collection. The line, designed by Alex Carleton, founder of Rogues Gallery, features ready-to-wear and accessories inspired by the brand's formidable history as our country's (and especially Maine's) preeminent outdoor outfitter. SupermodelMaggie Rizer (who became my first mannequin crush upon viewing her in, fittingly, a New England-themed spread in Vogue's February 2000 issue) serves as the face of the campaign.

This photo comes courtesy of James Wilson of Secret Forts. The peep-toe brogues are, obviously, mine. The nail polish is "Kennebunk-port" by OPI.

In a brightly lighted corner, past the inspiration board (as pictured below) and the oyster bar (built into an old canoe), a coterie of impeccably dressed bloggers swapped war stories and fabric swatches. I felt very, very honored and humbled to be part of this group - many of whom I have followed and admired as they built their mini style empires on the worldwide web. Among the dapper to whom I was newly introduced are Michael Williams of A Continuous Lean; Kate Jones, designer of Ursa Major jewelry (and previously at Rogues Gallery) and Freemans' hostess with the mostest; the electric and impossible-to-track-down Foster Huntington of A Restless Transplant; Emil and Sandy Corsillo of the Hill-Side; Kyle Hackett of Selectism; Sean Sullivan of The Impossible Cool; and Randy Goldberg and fellow Missouri alum Paul Underwood, both of Urbandaddy. Of course everyone present sported their all-American finest, but this boys' club (and Kate) took the Trad cake.

The collection itself was a mix of staid separates and all-American extras. I suppose the timeless quality was an homage to L.L. Bean's Waspy lineage, but Carleton spruced things up with contemporary Trad styling. Topsiders, Boat 'n Totes, and sneakers all stole the spotlight from chic but practical outfits, a madras shirtdress (which could have been a contender if not for the absence of some mysterious "It Factor", which Max and I debated but could not for the life of us identify), and an enviable Breton striped sweater, worn with shorts and TOMS.

The models appeared sufficiently bored, as models often do.

As usual I found the menswear far more inspiring: a particular pair of Nantucket red shorts set my heart aflame, as did a mishmash of blazers and button-downs. Nip in the waists, add some heels to those bluchers, and pass me a (bright red) lipstick. I'll make the boys' duds cocktail-worthy faster than you can say, "Lake Androscoggin."

Post-show we swilled and were swell at the Ace Hotel's gorgeous new bar, which cemented its status as my new favorite place in all of New York City when I looked up to find an enormous American flag nailed to the wall. If you visit (and you should) order an old-fashioned and the grilled cheese sandwich. You'll probably see me there, dancing on tables in my favorite winter whites (and the Boyfriend Fatigue Jacket).

Many thanks to Max Wastler for extending me the invitation to this swishy and long-awaited event. Check out more coverage and photos at All Plaid Out, Guest of a Guest, and Secret Forts.

The new favorite.

On Friday I visited J. Crew's flagship in the Flatiron District to poke around the sale section and see what's new. Style director Jenna Lyons' sensibility about mixing high and low, new and old, fancy and casual, is a major source of inspiration for me, and while I cannot credit her with my discovery of the cargo short, my friends might certainly blame her for approving them as evening wear.

I love a deal and rarely purchase retail, preferring to hold out for sample and seasonal sales, but this jacket, the Boyfriend Fatigue in olive drab, practically leapt onto my back. I could not leave without it.

I have determined to wear it every single day for the rest of my life (or at least until spring bids adieu to jacket weather).

On Saturday night night I dressed it up with a skimpy LBD and black patent heels and gold hoops.

On Wednesday night I dressed it down for the L.L. Bean Signature Collection presentation with white jeans, platform peep toe brogues, and, most importantly, J. Crew's Lucite chandelier necklace. (When you hang with boys' club, it's very important to sparkle.)

I'll wear it in the summer with gold sequins.

I'll wear it in the winter with tartan and wool.

I have long needed a new sartorial security blanket, and this jacket most definitely fits the bill. I don't ever want to take it off. It gives the wearer instant street cred. What girl wouldn't look cool stomping down Chrystie Street in this tough coat and rich red lipstick, aviators hiding her eyes?

Note: Lovers of all things J.C. should add the J. Crew Aficionada to their daily reader.

Brooks Bros & Mad Men

On Tuesday I joined Max Wastler of All Plaid Out at Brooks Brothers' Madison Avenue flagship to celebrate the launch of their capsule collaboration with Mad Men. The limited line of suits created by Emmy-winning series costume designer Janie Bryant will be available through the end of the series' season.

Stepping off the elevator and into the label's second floor suit department was like stepping back in time. Tie clips and slick hair abounded, and the duds looked great (if a little safe, but that's fine with me. I have little need for fops and dandies and prefer my men traditional(ly dressed)).

For a much more informed analysis of the suits and the talent behind them, visit All Plaid Out.

My eye, however, was not on lapels and pinstripes, but on the guests present - almost all the young gents who work at Sterling Cooper. Salvatore! Campbell! Oh my lands! Outfitted in Brooks' finest they seemed perfectly "in character", save for artfully mussed hair. Michael Gladis' beard and Vincent Kartheiser's hipster shag, for example, were quite post-modern (although my phone number exchange with Vincent so that I might set him up with a dear friend was decidedly more old-fashioned). Draper and Sterling must have been at a board meeting because I searched and could not find them. Undeterred I knocked back another dirty and shot some stick with Kinsey and the boys. This good girl has gone Mad.

Saturday at the Flea.

On Saturday I joined Kate at the Fort Greene flea market. A strong easterly wind rent tents asunder and shattered at least one china set, but the stalls were crowded, the sky blue, and autumn all around. I knew the moment I arrived that it would be a successful trip, that everything I could ever want was hiding amid racks of vintage furs and old cedar boxes filled with locks and keys. All I had to do was dig.

One of my favorite finds ever, this life preserver was pulled up from the bottom of the Gulf of Mexico. Alas, I could not take it home with me. You can find it and other fun sea-faring trinkets at Three Potato Four.

Keeping with the nautical theme I present a fresh label on old plaid. This buffalo check was made in the U.S. of A. by Old Ironsides. I should have bought it for the schooner logo alone.

This flag, made by Valley Forge Bunting, measures five by nine feet and is made of 100% cotton canvas. It came home with me, of course.