Last week, I shared a timely post all about styling sneakers with suits which is a look that takes a usually buttoned-up look and dresses it down. Given how of-the-moment wearing sneakers to work is, I decided to create work looks with separates to create business-casual looks.
While, of course, we want to be able to wear sneakers with just about everything, the sneakers you style with your more casual work looks mustn’t look like out-of-place afterthoughts. There are some work silhouettes that, no matter how you try, won’t work. So in addition to sharing outfits, I will also be giving tips on what to avoid to make your sneakers with separate outfits look purposeful. Let’s take a look at what I’ve put together.
SNEAKERS WITH SEPARATES FOR WORK: COMFORTABLE OUTFIT STYLING FOR BUSINESS-CASUAL WORKPLACES
OUTFIT #1

Trouser skirts have been bubbling to the surface for a few years now. They are a fantastic way to create an easy tailored work look that doesn’t involve pants. Unlike pencil skirts, sneakers with trouser skirts pair well together. On the other hand, sneakers with a classic knee-length pencil skirt can look a bit like that 80’s working girl reference I mentioned last week where women would change from pumps to sneakers for their commutes.
In this look, I styled a black trouser skirt from Whistles with a black and white strip button-up shirt from Everlane. Pop the collar a bit, roll up the sleeves and it looks easy and chic. I own this shirt in blue and white stripe and love the relaxed shape, the fact that it doesn’t gape and doesn’t require ironing. I finished the outfit with black and white stripe Adidas Samba sneakers, a black belt from Aritzia, and drop hoop earrings from Jenny Bird.
OUTFIT #2

I styled this next business-casual look using this client-favorite jardigan from MM. Lafleur that works belted, unbelted, or with the belt tied in the back like a trench coat. I styled the cardigan with another client favorite, Quince’s straight-leg ponte pants. Under the jardigan, I layered a third piece, also popular with clients, Theory’s silk georgette shell. The outfit is finished with sneakers from Dolce Vita and a pendant necklace from Sézane.
OUTFIT #3

For work environments where jeans are acceptable, I created this polished denim look. A client recently purchased this check blazer from Veronica Beard and styled it here with a purple short-sleeve sweater that picks up the purple in the blazer. I paired these pieces with cropped wide-leg jeans from J.Crew and finished the look with grey Voile Blanche sneakers, a grey belt, and purple hoops from Machete.
OUTFIT #4

While technically not a separate, I wanted to include a business casual dress like this to show it with sneakers. Dresses and sneakers for work can be tricky but definitely not impossible. A sheath dress and sneakers, for example, definitely do not translate as well with a pair of sneakers like a style like this Argent dress does. I styled it with a pair of light blue sneakers from Puma, a silver statement necklace from Madewell, and an Apple Watch band from Quince.
OUTFIT #5

In this last outfit, I styled this layered look for work with these grey wide-leg pants from Aritzia, a burgundy and white striped button-up shirt from Banana Republic, and a navy and white striped 1/2 zip from Kule. I finished the outfit with burgundy sneakers from Rag & Bone, a burgundy belt, and simple studs from Oradina.
SHOP FOR MORE SNEAKERS
Check out last week’s post to shop for more sneakers for your workwear looks.


Today, it’s raining here. So, I’m pairing quick dry beige pants, navy RL sweater, navy barn coat, rain hat and white sketchers I’ve waterproofed. I’ll stay dry, be comfortable and feel chic enough for lunch out and a book talk meeting…
I like that you included the maroon sneakers; often times it seems like white or off-white or mostly-white sneakers make these looks work. Would adding the maroon belt and shoes to various outfits provide enough to not make the sneakers look like an afterthought? Or does it require a 3rd piece (non-accessory) like the maroon stripes in the shirt in your example?
Thanks!
I don’t wear maroon, but like burgundy and have several pairs of shoes, from ballet flats to knee-high boots. I don’t wear belts, but would either put on a burgundy scarf or a top/cardigan. Also lipstick and/or nail polish. I feel burgundy shoes need something else in a similar shade to make the outfit work. Hope I was helpful.
Trouser skirt? Can you translate for a confused Brit? Loved outfit 2. effortlessly cool.