I Promise These Workwear Staples Aren't Boring—How I Style Them in Office Outfits

As a freelancer, I don’t traditionally enter an office everyday, but lately I’ve been working from a shared workspace that has boosted my sudden urge to “dress up” for work. It’s actually helped my focus and energy. This opportunity to take the effort to get dressed for very light workplace interaction has rewired my styling approach, and I wanted to share my findings to those who might need a spark of inspiration for office outfits.

I wanted to focus on four key basics that every office go-er should probably have already in their closet: a little black skirt, a striped shirt, black leggings, and a cardigan. My personal style usually involves a great pop of color or two, but I understand how that can be distracting in a more buttoned-up setting. So in the spirit of ‘90’s Carolyn Besette at Calvin Klein, I kept to neutrals, but reworked them in a way that feels a little less pared-down minimalist and a little more somethin’ somethin’.

Refresh the Little Black Skirt

I constantly troll my favorite designers on The RealReal from “price low to high” for hidden gems at a great deal, and a simple black skirt almost always kicks off the lower tier. I wondered why this particular item isn't valued more, because I see it as an opportunity to purchase a very well-made workhorse for the wardrobe.

Because I’m always on the hunt for something unusual, my favorite little black skirt I own is a super lightweight wool 1997 Miu Miu style with a super high slit. While I definitely have worn this in a super leggy, NSFW way, as it was shown on the runway, I often layer it over long tunics or shirt dresses, sometimes with a cool colorful or patterned pair of tights. This time, while dresses over pants have been on my mind, I tried it over a pair of simple tapered trousers and absolutely loved the effect. I paired the combo with a simple vintage Gap wool collared sweater, black flats, and a pop of a color in a bag (if that’s allowed at work!). It all came together as an effortless and comfortable outfit, but just a touch of that cool-factor that turns otherwise boring trousers and a boring skirt into something much, much less boring.

Refresh the Striped Shirt

First things first, do yourself a favor and get a bigger striped shirt—your elbow crease and bust will thank you for the extra room. Second, take that big shirt and pair it with an equally oversized jacket. This silhouette automatically brings very square office basics instantly into cool, effortless French girl territory.

I threw a simple cotton turtleneck under the shirt because it’s one of my favorite layering hacks for warmth that also makes it feel more sophisticated. The third step is to pair it all with something small to avoid the messy, clown-y feel of dressing up in Dad’s clothes. So, I took a pair of fitted cropped jeans (you can definitely swap for a black cropped ponte pant, if jeans are a no-go at work), a pair of sock booties, and a tiny nylon Prada bag to play up the oversized proportions. This one feels good for almost anywhere else I’d want to go from a casual dinner date or drinks with friends after work.

Refresh the Black Legging

Okay, this one is also dependent on the dress code of your office, but I think it can be a very chic base that's also quite comfortable. I'm never, ever gatekeeping my obsession of Sacai shirt dresses. (I quite literally have six different ones for various seasons, and have worn them for years and years.) I love ones that are a little funky or “reworked,” and this one has sweater sleeves—a great added texture. I added a blue wool sweater vest on top for a monochromatic statement. They're always the perfect length, too: never too long for bare legs, long enough to cover your butt if you’re pairing leggings underneath (a crucial element for a professional setting).

Black leggings and loafers anchor the look that I finished with a secondhand Prada nylon backpack, one of my favorite work essentials. I also want to note that I think it’s worth investing in a very thick cotton or cashmere pair of leggings that have great opacity and feel closer to pants, instead of trying to get more mileage out of a pair of workout ones. The nylon will throw off the polished vibe.

Refresh the Cardigan

I once went through my very good friend Christina’s closet and helped her slim down her cardigan selection (she had just a few too many), but I was thinking of her when I put together this outfit. Mind you, this super old Marc by Marc Jacobs one of mine is a little funky, with the layering effect and two tones, but I wanted to show how playing with neutral colorblocking can still feel interesting, even if the colors aren’t super bright.

I love the idea of a mismatched twinset with a short-sleeve or tank sweater in a contrasting color, so I chose a cream cashmere knit to go with my cardigan. I also added a navy trouser, black loafers, and a black patent hobo bag with big silver hardware for a little more texture. It felt more interesting than the simple sweater-and-trouser combo I default to in the winter. I highly recommend adding some non-long-sleeved sweaters to your wardrobe as a more polished trans-seasonal staple and an extra layer with cotton shirts, long-sleeved tees, turtlenecks, and, of course, cardigans of a different color.