“…I didn’t want to wear a sack dress myself; I just wanted to be friends with a woman who did. She’d be smart, sophisticated, witty, and brave, and together we’d bond over this haute hoot.” John Waters, “The Dress that Changed My Life,” Harper’s Bazaar, September 2014
Shapeless sacks. These are the two words that best describe my wardrobe, according to my always-natty brother. His next three words would be saggy diaper pants (AKA, harem or MC Hammer pants). Super sexy, I know. Tunics, caftans, sack dresses, oversized shirts, drop-crotch pants – if it’s large or voluminous, boyish or boxy, it’s in my closet. But it wasn’t always this way.
You see, I spent my formative sartorial years working in retail, where the number one mantra was: Look. The. Brand. So my “style” was essentially dictated by what was currently in store and what I could afford. I went from saving up my $4.75-per-hour Foxmoor Casuals paycheck to buy Sasson jeans (no Levi’s allowed) to sporting a lab coat, chunky gold earrings and beaucoup de maquillage at the Saks Fifth Avenue cosmetics’ department to 15(!) years dressing for success at Ann Taylor, Inc., which was an entire sartorial journey unto itself. From shoulder-padded Murphy Brown jackets to a boucle micro-mini skirt suit and chunky shoes straight off the set of Ally McBeal,to wishfully channeling Carolyn Bessette Kennedy in her knee-high boots, pencil skirts and fitted v-neck sweaters to an unfortunate stretch — and I do mean stretch — wearing the same elastic-waist black skirt and striped knit top every other day for the last two months of my pregnancy.
But, in an unexpected turn of events, at the end of my leave, I didn’t go back. I quit. And after the baby coma wore off and I reluctantly put away my maternity pants, I floundered in post-pregnancy schlumpiness. Whoever coined the phrase nine-months on, nine-months off is an idiot. (Why am I not losing the baby weight? Is it the daily chocolate croissant from Mazzola Bakery? Watching Ina Garten all day and then cooking up a storm every night?) Finally, driven by A) going back to work, and B) having had to pour myself into Spanx for my 20-year reunion in order to wear a tea-length, fit-and-flare black dress (redeemed only slightly by my still-nursing boobs; hey, guys – look at me! I finally got some!), I realized I had to pull myself together. After nearly two decades in retail, I had finally broken free of looking their brand and needed to find my own brand. But without dress codes, style guides or new deliveries to guide my purchases, I was unmoored. This was 2005, so while the interwebs were a resource, there was no Pinterest, no Sartorialist, no WhoWhatWear.com—there was barely Facebook and nobody posted anything interesting, let alone stylish. What should I wear? What could I wear? What did I like? Where would I shop?Whoever coined the phrase nine-months on, nine-months off is an idiot.
So I did what any smart girl would do: I placed a 911 call to my GBF. Who better to help me rid my closet of all the hideous and now ill-fitting career-gal clothes and make a fresh start? Together, GBF and I made piles for the consignment store and the Goodwill: sad suits I no longer felt obligated to wear, cashmere sweaters that no longer fit and blouses, belts and bags that were, well, just NO. And there we were, laughing over triacetate, when he pulled out a navy wool Harvey Faircloth sack dress and flung it onto the consignment pile. “STOP!”I shrieked. “I just bought that!” It was like someone cut the music and turned the lights on at our disco party for two (insert sound of needle scratching off a record.) GBF looked at me in horror. I looked at him with defiance. “Well,” he said, tentatively (and hopefully), “perhaps you could belt it?” And that’s when I knew, though I valued his opinion and loved him dearly, on matters matériel, I was going to have to go my own way. The way of the sack dress.
The seeds of my style were sewn (no that is not a typo) by my needle-crafty mother and sorceress/seamstress grandmother. It is them that I credit for my obsession with comfort and caftans. Hosting dinner parties in our gold-veined, mirror-walled dining room, my mother always wore a glamorous up-do and an authentic Tahitian muumuu or an exotic, colorful hostess dress she had created. My well-heeled grandmother, whom we visited every summer in Southern California, always traded in her tidy office attire for one of many elegant, floor-length housedresses (which she whipped up in multiple fabrics) as soon as she walked in the door. (This was a woman who cleaned her pool and washed her car in a caftan and high-heels and did headstands and splits daily to keep in shape. I can only aspire.) I had always admired this easy, glamorous shape, and now that I was free from the constraints of The Code, I could indulge my own inner “hostess.”
To be truthful, before the great closet purge, I had actually begun to flirt with some actual shopping and dressing and choosing. Such freedom! Those who haven’t the Stockholm syndrome of spending two decades under the dictates of a dress code coupled with a deep employee discount will never know the thrill of promiscuous purchases and not giving a flying frock what anyone thinks of your outfit. I discovered Bird in my own Brooklyn neighborhood (shopbird.com) and Impulse Seattle online (now Totokaelo.com) – both early purveyors of loose and languid. I perused LaGarconne.com, a pioneer of androgynous yet elegant understatement. Uniqlo launched in the U.S. (with a much more Japanese bent than they currently offer), perfect for simple basics. Isabel Marant made grey sweatpants chic. Pajama jeans and harem pants were suddenly easier to find. I became obsessed with Zero + Maria Cornejo and now own more pieces than I need, but not as many as I want. Slowly but surely, with each new purchase, I shifted my sartorial slant away from the fitted and toward the full.
So here I am, 10 years free of my retail-driven regalia and deep into ManRepeller/Leandra Medine territory. I work at a very chill creative agency, where unless I have client meetings I don’t need to “dress up” — but I usually try to look presentable just in case. (Thus, the abundance of ever-versatile sack dresses in my closet.) I walk nearly a mile to the subway and back, plus lots of schlepping in between so comfortable shoes are a must – usually ballet flats or oxfords, though I do love a good taxi shoe every now and then. Around the neighborhood, its camouflage pants or baggy jeans and a sweatshirt, often matching my 10-year old son.
How would I describe my style? Japanese bag lady meets adolescent skate-rat. Or quirky Santa Fe art teacher who only wears neutrals and eschews accessories (except for the occasional bling.) Or, more likely, lazy working mom who just can’t deal with fussy clothes. I like practical, classic, architectural, simple, modern, easy, sometimes slightly mannish, but most of all comfortable pieces. I wear a lot of black, it’s always appropriate. Also navy, grey and nude (the color, silly.) But I occasionally indulge in a graphic print or a little POC (pop of color.) I like to put on one or two items and be done. I believe less is more, unless more is more (particularly when it comes to sequins.) And I am convinced that a sack dress is perfect for any occasion.
With the luxury of apparel independence, I base my choices on three mandates:
- I love it.
- It’s comfortable.
- I will wear it a year from now.
I followed the “does this bring me joy” rule long before Marie Kondo folded it up and tucked it into our sock drawer — I want things in my closet that make me happy. (Though I have to watch this one — again, with the sequins!) Joy can come in the form of glamour or ease. Preferably both. It absolutely has to be comfortable. Perhaps because I’m fairly tightly wound, I prefer the freedom of a flowing frock to a snug-fitting skirt. Or maybe I just like a more forgiving silhouette in my old age. Either way, there’s really no point in going around all day unable to breathe. Or eat. Or run for the subway when you’re totally late for a meeting. And, finally, aside from an occasional cheap thrill at H&M, I can’t really do trends. I’d rather have fewer things but wear them longer. I try to follow a one in, one out rule, but when I do overindulge and need to purge, I enlist the TheRealReal.com You clean out your closet. They send you a free Fedex label. You receive 60% of the selling price. Done and done.
My husband respects my repelling ways. “When you bring things home, they look like grandma clothes. But when you put them on they’re cute,” he says, with forbearance. His crushes on Tilda Swinton and Jenna Lyons reassure me that he’s down with mannish style. My son doesn’t usually notice what I wear, though he once told me that my coat looked like a garbage bag. But he does think it’s cool that we have the same black-checkered Vans, so I guess we’re even. At any rate, I’m happy with who I am and how I look, and I’m glad that I never have to dress to someone else’s code again. So if you’re tripping around Brooklyn or Lower Manhattan and see a short, sturdy girl in a shapeless sack or saggy diaper pants, that will be me. And though my brother and GBF may not approve, I’ll have a smile on my face because I’m always nicer when I like my outfit.