My favorite skirts in my wardrobe cover every category. There are neutral wool midis from J.Crew and Joseph that complement knee-high boots and chunky loafers. When paired with draped scarf sweaters and button-down shirts, my Akris laser-cut skirt and a printed organza midi from Zara add texture and funky prints. For the work days when I’m feeling extra cozy, I look at knitted sweater dresses that can be dressed up, or down. Malene Birger is always my go-to for creamy, chunky cable knit styles while Norma Kamali has a great waist-cinching option for those after-work dinner dates and events. There’s a pleated number from Miu Miu (mine is the vintage version, but this chocolate brown one is a dream!) and leather options from Co and Veronica Beard in my rotation, too.
My pantsless journey is, apparently, just beginning. I may have ordered two more this month—don’t tell my husband. The skirts and dresses that make up a majority of my winter wardrobe, ahead.
Leather Weather Midiskirts
The leather midiskirt’s effortlessness—and transitional appeal—is a go-to for my city-dwelling lifestyle. On casual days, I like to wear them with oversized turtlenecks (à la the Olsens) and moto boots. For work weeks, you’ll often see me sporting one with a crisp poplin shirt or fitted crewneck.
Let’s Get Funky
I may gravitate toward neutrals 90% of the time, but every so often I like to indulge in a little playful print. Zara’s organza skirt looks more expensive than it is, and everytime I wear it, I end up receiving a ton of compliments. Another coveted skirt of mine is Tibi’s recycled wool option—it’s designed with a built-in boxer effect that looks so good with a tucked button-down and glossy leather belt.
Knitted to the Max
Dresses, dresses, dresses—where would my wardrobe be without a good rotation of dresses? My most recent purchase includes this under-$300 option from Mango, which is both a skirt and a turtleneck—the best of both worlds, in my opinion. For laid-back days, I reach for Cos’s grey knitted shift dress. It looks too chic with tall kitten-heel boots and tights.
Something Wooly
I’m not willing to forgo my skirts come winter. If anything, the seasonal shift makes me more determined to challenge myself and my layering techniques. The wool midi is the perfect solution to cold-weather problems. This J.Crew skirt comes in a versatile cream, with an A-line silhouette. It’s perfectly heavy. Speaking of heavy, Joseph’s Duparc skirt cascades to an asymmetric hem and is weighty like a well-made sweater.
Pleats, Please!
In my youth, I had a Blair Waldorf obsession. Her Upper East Side prep school aesthetic never left my mind or closet, and even years later, I still embrace uniform codes. These days, instead of going full girly-girl, I lean into Miuccia’s motto of “ugly chic.”My favorite part about a pleated skirt is that no two are the same. Just take a look at the silky brown lines cut into JW Anderson’s skirt, or the voluminous pleats in Toteme’s cotton blend maxi. I think I’ve worn both into the ground—and rightfully so.