Are You Unintentionally Horrifying Your Boss? 6 Office Dos and Don’ts

Navigating a professional relationship can be difficult—from communicating clearly to managing expectations—and when that relationship is with your boss, it gets even trickier. Accordingly, we thought we’d get some career pointers from one of the best bosses we know (and full disclosure, this editor’s boss), Who What Wear Co-Founder, Hillary Kerr.

Ahead, the top three dos sure to impress, and the top three don’ts that just might horrify. Plus, just because we like you, we threw in some office outfit inspiration and killer shopping options to elevate your workplace wardrobe. 

“No one likes having to circle back on something, which is why communication is so important. Even if the news is that you haven’t finished something, keeping your bosses abreast of your progress is always a good thing.” –Hillary Kerr


“People who are helpful and willing to take on tasks outside the scope of their day-to-day work are always appreciated. If you go out of your way for your boss, your boss is more likely to go out of her way for you. Unless she’s evil, in which case, I’m sorry.” –Hillary Kerr

“It’s always strange to me when someone doesn’t seem to know what other brands, companies, or people in their industry are doing. Whether it’s merely to learn what not to do or sparks an idea of your own, you should always pay attention to other businesses in your category. Information is power.” –Hillary Kerr


“People who get the most done, and who are the most respected, generally speaking, are the ones who acknowledge the help they get from their colleagues and teams.” –Hillary Kerr

“Is your workload overwhelming? Are you having trouble with a colleague? Do you dislike a project? That’s fine, just come with some potential solutions for your problem. There’s nothing productive about just saying “no” and leaving it at that. Have alternative ideas and think of ways to resolve the situation; it shows you care and that you want to fix things.” –Hillary Kerr

“From the moment you resign until your last day in the office, work twice as hard. Okay, maybe that’s an exaggeration, but the point is your behavior during those last few weeks is what your boss will remember about you. It is your legacy, so don’t slack, show up late, or suck, in general.” –Hillary Kerr

A.L.C. Schoolly Top ($430)

We’ve seen a lot of matching sets in the past few months, and this floral version is one of our favorites.

Bianca Pratt 10K Yellow Gold Initials Necklace ($275)

A delicate letter necklace is an excellent way to personalize your office look.

Zara Mini Shopper Bag With Pocket ($60)

You likely have a standard black purse, so why not shake it up with a color perfect for fall?

Massimo Dutti Cashmere Dress ($280)

This effortless shift was made for layering. Pair it with a sleeveless button-down shirt now, and try a turtleneck underneath for fall.

Rag & Bone Jo Anne Shirt ($295)

You’ll be surprised how often you reach for this classic striped button-down shirt.

Front Row Shop Cut Out Shorts ($41)

If you can get away with shorts at your office, we recommend this tailored pair.

meli melo Medium Thela Bag ($813)

Call off the search—your perfect work bag has been found.

MM6 Maison Martin Margiela Oversized Jacket ($766)

From the oversized fit to the unique material, this blazer is sure to elevate any outfit.

Loeffler Randall Remy Pumps ($325)

The shape of these Loeffler Randall pumps is especially appealing.

Wilfren Calais Sweater ($145)

Pair this chunky knit sweater with a crisp collared shirt.

Melt Bhalay Mohawk Scarf ($550)

How are we justifying this splurge? It’s sure to become a signature piece, guaranteeing a low CPW (cost-per-wear).

Meredith Hahn Luna Studs ($55)

Your basic studs will be jealous of these edgy, yet delicate, earrings.

Club Monaco Nealy Shirt Dress ($229)

Your office outfit should never look too contrived—keep it simple with a printed shirtdress like this black and white version.

ASOS Pleat Front Bonded Midi Skirt ($77)

This is the sort of pastel hue you can wear year round.

Have you ever done something you regret at work? What about a time you excelled? Share your story in the comments below!