Casual Friday.

I attended Catholic school from first through twelfth grade.

In general, uniforms were handy, I think: no fights with my parents over what I could or could not wear on a daily basis; no keeping up with the cool girls by copy-catting their “cool clothing” (though, I still found ways to misspend my parents’ money by demanding specific types of shoes and fleeces and backpacks that I coveted on the better-appointed girls in my class); no daily dilemma over what the hell to wear.  Oddly enough, during my high school years, the shabbier you looked, the cooler you were.  Frayed skirt hem?  Great.  Bleach-specked polo?  Fabulous.  Clunky brown shoes with the back flattened down into a make-shift mule?  The peak of chic.  And ratty, tattered sweatshirts from older brothers or, better yet, boyfriends with our brother school’s insignia on the front?  Epic.  My sisters benefitted from my trailblazing in this arena: whereas I showed up on day one of  high school wearing a banana yellow, so-fresh-out-the-bag-it-still-had-creases-in-it polo and a knee-length forest green skirt with knife pleats so crisp I could have sliced my hand with them (#dorkusmaximus), my sisters waltzed into class wearing all the clothing I’d altered and broken in to the point of acceptable threadbareness.

“Why would you want to look so bad?” my best friend, who attended public school in Arlington, marveled when I tried to explain the ruffian-chic vibe we’d channeled as teens.

Because, fashun.

I have thought about fashion a lot over the years, and have come to the unsatisfying conclusion that fashion defies logic.  Why do we cotton to kitten heels one season and then, two later, discover that nothing could look stodgier?  Why have I been wearing tattered jeans for the last few seasons, and, before that, only skinny jeans, and before that, colored jeans, and before that, flares?  (Ugh, flares.)   Fashion is far more about emotion and, more specifically, aspiration than anything else — about wanting to fit in, about desiring to project a certain image or lifestyle or personality, about hoping to be somebody or affect a certain kind of reaction that leads other people to believe you are that somebody you want to be.

In high school, we were collectively trying to portray a cool nonchalance, an I-can’t-be-bothered-by-your-traditions positioning.  Our admittedly affected insouciance dovetailed with, or borrowed from, or otherwise reflected Abercrombie’s “undone” ethos, and Abercrombie was king at the time.  Abercrombie, with its borderline pornographic catalogues (how did my mother let us shop here?) and heady cloud of cologne and blaring music (“I’ll wait outside,” my mom would sniff) and overpriced, intentionally faded and tattered wares, made me feel as though I was the type of girl who spent her summers at the beach with sunkissed, sandy hair, riding around in roofless Jeeps with older boys who would sneak me beers around bonfires.  (Though absolutely zero of that was true.)  Abercrombie was exactly what my country club upbringing was not — or maybe it was the rogue inversion of my rearing: it involved polo shirts and khaki and plaid, but polo shirts that were too tight, and khaki that had distressing to it, and plaid skirts that were too short.  Abercrombie felt like trespass, like late nights past curfew, like sneaking behind fences, like dangerous and youthful firsts.  By skirting the uniform regulations, we were living out the same devil-may-care fantasies.

I chuckle at myself, thinking back.  My parents must have rolled their eyes as I’d trot into Founder’s Hall in the morning, hair a messy top-knot, plaid boxers peeking out from beneath a 4″ long, frayed skirt, polo whitened with bleach.  They must have looked at each other and said, “Pick your battles.”  They must have gritted their teeth as they saw me recoil in disgust from the beautiful cable knit sweaters and velvet skirts they’d ply me with, as I opted instead for intentionally destroyed, far-too-revealing separates.

But, truth be told, I’m still not far off from the thirteen-year-old flirting with teenage angst and dreams of innocuous delinquency through her clothing choices: I still dress myself out of desire.  I dress myself to tell the story of who I want to be.  And sometimes that’s The Girl Who Reads Vogue and Knows What Bag Is IT This Season, and sometimes that’s The East Coast Mom Who Was Raised at the Country Club and sometimes that’s The Boho Girl Who Wears an Embroidered Maxi and Barefeet and Probably Does Something Artsy for a Living, and sometimes that’s The Polished Executive Heading to the Board Room.  All of these versions of myself, so easy to access with the careful selection of a handful of articles of clothing.

Who do you dress up as?

I’ll tell you that these days, I’m dressing as Mom Who Just Needs to Get 1000 Errands Done While Looking Semi-Put-Together.  Below, my favorite picks for Casual Friday.

Casual Friday Look No. 1: The Statement Sweater.

More often than not, my day-to-day uniform looks something like this: statement sweater ($69), my high-waisted jeans (ain’t nobody got time for plumber butt — $189), and my Gucci slides ($680).  I also love the fur-trim ones, even though my brother in law saw them and remarked: “It looks like there’s a dead squirrel attached to the back of those shoes.”  HAHA.  Also, more great slouchy sweaters here.

Casual Friday Look No. 2: The Statement Shoe.

As you’ll probably gather, when I’m trying to look casual but pulled-together, I tend to focus on one special item in my outfit and keep the rest pretty straight-forward.  So, if I want to wear my latest Gucci acquisition ($595), I’ll keep the rest of the look basic and finish it off with an inexpensive and unfussy red top ($25) and some relaxed-fit jeans (people go nuts over the styles from Re/Done).

Casual Friday Look No. 3: The Striped Dress.

I love the striped shirtdresses that have been all over the place lately because a) they look “done” without being too uptight; b) I don’t need to figure out what pants/jeans/skirt to wear on the bottom; and c) they tend to be nursing-friendly.  I pair mine (this shape is also up my alley — I love a nipped waist) with Tod’s loafers.

Casual Friday Look No. 4: The All Black Errythang.

If I just can’t be bothered to think about anything, I throw together anything black in my closet.  Lately, this has meant a black button-down blouse (mine is the Blythe from J.Crew, no longer available in black but this is similar), black silk joggers, and my new unnecessary purchase of the month: pearl slides.  (Incidentally, very comfortable.)  If you like the slides but are not about to drop anything close to $100 on them (or, worse yet, the full $750 for the Miu Mius!), I found these lookalikes for $28!  Also, oversized black shades — these are my absolute favorites these days.

A Few Other Casual Friday Finds

Other pieces to mix and match with my go-to looks:

+Still obsessing over this chic blue sweater — what an unexpected hue!

+I’ve never been a Chuck Taylor girl.  I always favor my classic Supergas.  (Chuck Taylors: Supergas :: Bowling: Tennis.)  But these calf-hair ones in chic camel may make me change my mind…

+A great alternative to a black silk button-down.

+Cashmere for $160!  I love this in the navy or camo colors!

+My latest pearl acquisition.  (Also check out these beauties.)

+Not black, but these blush pink joggers look so easy and comfortable.  I’d pair them with pearl slides and a simple black pullover sweater, or a white silk button-down.

+Throw this cape over your all black look, and you’ll slay.  Seriously, I just decided I’ll wear this look tomorrow — black jeans, black sweater, black Gucci mules, and this.  Done and done.

+Still daydreaming about this bow blouse.

+This sweater dress has the same ease-of-wear as a striped shirtdress.  Love.