Any girl that attended Catholic school from first grade through her senior year of high school (ahem, me…) is bound to have a love-hate relationship with plaid. On the one hand, it conjures memory of itchy kilts, strict rules, and…well, school. On the other hand, the uniform made life so easy and truly sharpened my fashion sense (hey, even a headband served as a platform for self-expression). And even I can appreciate that all plaids are not made equal — some evoke a preppy New England vibe; others, a slightly rebellious grunge aesthetic (I don’t go near the latter…) At any rate, this season has been chock-a-block full of eye-catching plaid pieces, and I particularly appreciate the mash up of the utilitarian-militarista-plaid looks I’ve seen by the likes of Rag & Bone and Dries Van Noten, among others. How to get the look without appearing like a vampy schoolgirl? One safe bet is a plaid topper, like this toggle cape ($268, Steven Alan):
Add a utilitarian-chic tote ($230, Clare Vivier) and some classy brown leather gloves $250, for good measure
Meanwhile, how about this shrunken blazer (love the contrast-fabric beneath the collar — $160, TopShop) with a pair of plaid shorts (now, I know I said I was on the fence, but there’s something so…to die for about this combo! — $65, TopShop):
Perfect with a rich-looking tote (Alexander Wang has that it factor right now — $1,300, Liberty) and some heathered flats (I just adore these cap-toed flannel Lanvins — $500, Bergdorf Goodman):
Alternately, why not pair this shawl-collar sweater (A.P.C., $310, La Garconne) with a wool skirt (Alexander Wang, $425, Net-A-Porter — note that you can find a FAR more affordable version of this skirt at Old Navy for only $23…)
Finish with tweed headband (Jennifer Ouellette, $60, Barney’s) and this suede shopper ($650, Barney’s) — something about the contrast in textures and tweeds updates the whole look and brings into fashion-forward territory, without making you look like a nut:
For a similar but slightly bolder aesthetic, go flannel-on-flannel for a truly winterized look with a cozy gray blazer ($375, Steven Alan) — I’d wear it with the collar flipped up! — a silky blouse ($78, Nordstrom), and a plaid mini($29, OldNavy):
Channel Blair Waldorf with a pristine white blouse (Vanessa Bruno, $350, Net-A-Porter) tucked into a plaid skirt ($135, La Garconne):
I like the skirt waist worn a little high and the top neatly tucked in for the perfect modern silhouette. Top with this darling camel-colored felt cape ($378, Juicy Couture — note that MaxStudio has an olive green hued variation of the cape below on sale for $78!):
I like the slouchy look of the coat against the prim-and-proper get-up. In my mind, a “grown-up” shoe is in order, like this chic suede pseudo-bootie (more flattering because of the low-cut front — on sale for $124, Nine West):
Glossy gold accents are most definitely the way to go by way of additional accents — they feel weighty and “grown up” in the comparison to the plaid skirt. I like the idea of these gold disc studs (Gorjana, $35, PiperLime), this chunky Fallon ring ($215, ASOS), and this heavy chain bracelet ($138, A Bientot):
This forest green scarf would truly tie everything together ($295, Barney’s):
One thing I’ve done quite a bit this season? Tucked various blouses and button-downs into one of my two go-to black pencil skirts. I recently wore a plaid button down (in a dressier cotton fabric — don’t think this will quite work with a flannel; something like this $158 Steven Alan blouse would work) tucked into a high-waisted black skirt ($130, TheOutnet) and some pointy-toed black flats (Sam Edelman on sale for $42, 6pm):
This ladylike red handbag rounds it all out (Kate Spade, $325, Nordstrom):
I’m all about the tassel these days…
Now, while I’m have lots of fun imagining these skirt-and-blouse/sweater get-ups, my go-to “putzing around the apartment” outfit consists of a plaid tunic or oversized shirt (like the Rag & Bone tie-waisted one below — $355, Les Nouvelles — but Urban Outfitters has a fairly similar one for an affordable $48), leggings (I get mine from American Apparel for $26/pop), and my Tory Burch rabbit fur mukluks (I adore them — and they look very similar to these Manitobas — $280, Gravity Pope). I can’t help it — it’s just about the coziest outfit on earth. I’m sure Mr. Magpie is sick of seeing me in it…
I feel snuggled already. If I were heading outside of the apartment, I’d swap out the mukukuks for some leather boots ($298, Madewell) and add a rich leather tote (Michael Kors, $1,195, Net-A-Porter):
Finish with a be-tasseled Mulberry tote (swoon — $1,250, Mulberry) and — if you are daring — a mongolian fur vest, a la Olivia Palermo (chic-pea that she is — Michael Kors, $325, Net-A-Porter):
Finally, for just a POP of the trend, why not spruce up an LBD or a minimalista black-cropped-pants-and-black-sweater for work with this bold buffalo check tote ($74, ShopRuche)?
I like the idea of pairing any of the above toppers with a plain white tee, an understated pair of dark-wash denim, and some bright red flats (on sale for $62, Kurt Geiger):
Being as enamored of accessories as I am, I’d likely layer on a necklace (I l.o.v.e. this affordable little chain necklace! — $59, Talbots) and a pair of sparkly sunburst enorma-studs ($125, Charm and Chain):
