There are a ton of wardrobe philosophies out there these days, most of which concentrate on how to declutter your closet through wearing only what makes you feel happy and axing excess to hone in on your personal aesthetic. While closet detoxing — and more mindful shopping practices — are important aspects in your relationship with clothing, so is knowing when to not focus on sartorial limitations. For me, that means never labeling my clothes.

I’ve never had an “I can only wear this here” kind of mindset, like calling a tank a “summer top” or a bodycon mini a “going-out dress.” Having such rigid guidelines can cut a lot of the creativity (and fun!) out of putting together outfits and evolving your sense of style, and those two aspects are, to me, what getting dressed should be all about. To see if this mindset was universal (or determine if, actually, I just liked to break the rules), I asked five of my co-workers to partake in a style challenge: to wear their most scandalous clothing to the office without making HR bat a lash. Was it *actually* possible to look like a #Girlboss — and feel comfortable — wearing your tightest, most cropped, most cut-out pieces to work? Was it even possible to pull off? Read on to see the ways they hacked their slinky duds to fit their 9-to-5s.

Lee Schellenberger, Kit Designer


Tell me about your scandalous piece.

“This scandalous piece comes from American Apparel… so scandalous! It’s a fun palm print, a banana leaf, which is everywhere, and I like it. ‘Cause I’m very picky about prints. It’s good because I have high-waisted everything in my closet. So, with crop tops, you can change around high-waisted skirts, high-waisted pants, high-waisted whatever, so yeah, it’s the way to go.”


How do you usually wear it out when you don’t have to worry about HR?

“When I don’t have to worry about HR, I usually wear it with a high-waisted circle skirt. I would wear it to bars, like out-out. Or maybe on a really nice sunny day.”


Was it difficult to hack it for the office?

“Finding the right high-waisted dress pants to go with a crop top was the hard part, but once you do that, it was easy. High-waisted slacks, a cool jacket — the jacket has to look trendy enough to go with a crop top. It can’t just be your grandpa’s cardigan.”


Cortney Clift, Associate Editor


Tell me about your scandalous piece.

“It’s a simple black dress with low-cut sides from Reformation. I got it because you could wear it with a bunch of different things and it’s easy to put on — good for summer.”

How do you usually wear it out when you don’t have to worry about HR?

“With a bra that won’t show when I want to look really elegant or with a lacy bra that shows a little bit on the sides for fun. Or just like that with a denim jacket to the park or for brunch.”


Was it difficult to hack it for the office?

“No, it was easy to put on a collared shirt on underneath.”


Marisa Kumtong, Junior Designer


Tell me about your scandalous piece.

“It’s a really great crop top from Forever 21. I love it and I feel so good in it. It makes me feel really good when I go out — it fits my body well. It shows just enough, not too much.”


How do you usually wear it out when you don’t have to worry about HR?

“I would wear it with heels. It’s pretty simple so you don’t really have to mess with it too much; you just wear it and that’s all that needs to happen. That’s all the flair; it’s already all there. I don’t really like accessorizing too much; I keep it pretty simple.”


Was it difficult to hack it for the office?

“It was not difficult. I put on a blazer and I put my backpack on and I put a longer skirt on so it doesn’t show as much. Instead of making it look like a two-piece, I can pull it up to make it look like a one-piece so it’s more conservative for work. It’s so versatile; I love it.”


Katie Bukstein, Director of People


Tell me about your scandalous piece.

“My scandalous piece is a dress from this great boutique in NOPA. It’s great for a sunny day — you can dress it up or dress it down and it’s flowy, so you can wear it in warm weather or you can layer.”

How do you usually wear it out when you don’t have to worry about HR?

“Either wearing some sort of cool bra in the back, sort of open or depending on if it’s really warm, leaving it open entirely with heels to dress it up and some funky jewelry because the front is pretty covered.”


Was it difficult to hack it for the office?

“It was super easy to change it up for work. I just added a cool pop of color with a little tank top for a more conservative, fuller coverage. Throwing on a blazer, a vest or even a leather jacket would work, too.”


Beth Wischnia, Editorial Intern


Tell me about your scandalous piece.

“I got my scandalous dress at Nordstrom. I love the cutouts and I love the bright color, and I love how that’s it. I like things that are very simple with just one thing that makes it cool.”


How do you usually wear it out when you don’t have to worry about HR?

“Just like this! It’s something I would wear in Vegas or I probably would wear it to a very big night out. This is a little bit dressy and scandalous for me for going out here in the city on a normal night.”


Was it difficult to hack it for the office?

“It was difficult before I started. Once I put it on, it was so tight that I was like, okay, I can put a lot of things over it or even under it —I like the idea of a collared shirt under too; it looks much more conservative, which I tend to gravitate toward, especially when it comes to dressing for the office. I like the juxtaposition of the cutouts with the collar. The hardest part was covering the waist cut-outs, but I think it would work with a lot of different high-waisted skirts in neutral colors. So it wasn’t that difficult once I opened my mind to the idea of wearing it to the office. I‘ve never actually worn this dress, ever, so I had to kind of think how this would work!”


Kate Puhala, Style Editor


Tell me about your scandalous piece.

“I’ve had a really hard time finding the perfect jumpsuit. They’re always either too dressy or too casual or too patterned — I really like wearing black. So, this one from American Apparel just fit the bill for me. It’s plunging (front and back!) is really hot but not too racy, especially since the fabric and cut is so drapey. It’s really well balanced (and nice to give my butt a break from my skinny jean-only denim rotation).”

How do you usually wear it out when you don’t have to worry about HR?

“I keep it simple: a charm necklace or choker, a patterned clutch, some open-toed sandals, a pop of color lipstick and a good mani/pedi to round out the elegant feel.”


Was it difficult to hack it for the office?

“Not at all. I toss anything cropped over it. I’m obsessed with this ADAY crop top — it has totally replaced my need for a white work button-up, plus its sportier vibe suits my style better anyway. When the two pair together, it’s like a minimalist girl’s dream. Or for a more casual approach, I’ll wear a tight, short-sleeved crop top underneath — that was my uniform at BeautyCon this year.”


What are your style hacks for transforming your most scandalous clothing into everyday duds? Share your secrets in the comments below.