The #1 Question to Ask Yourself Before Getting Dressed for Work

We’ve written volumes on the subject of dressing for the office (take a deep dive with this article and this one), but if you care to simplify the topic, we came across a nugget of advice that captures the essence of everything you need to know. Liana Satenstein wrote for, “Stick with that old saying: When in Rome, you can wear gladiator sandals if you want—just as long as your higher-ups are wearing them, too.” Essentially, when you’re getting dressed for work, ask yourself: “Would my boss wear this?” If the answer is no, you shouldn’t wear it either. Asking yourself this one question helps solve any office outfit indecision, and will encourage looks that impress your supervisor.

Would you try this trick? Let us know in the comments, and scroll down to get inspired and shop pieces we’re certain your boss will love.


Imax Tree


Vanessa Jackman

Need Supply Luca Track Pants ($325)

Your standard black trousers are about to get shown up.

Aerin Faden D’Orsay Pumps ($298)

This deep crimson color is right on for fall.

Clu Striped Pleated Top ($271)

The traditional collared shirt just got a feminine makeover.

Botkier Leroy Cross Body Bag ($298)

This purse has just enough edgy elements to add interest to your ensemble.

Building Block Tassel ($95)

It’s all in the details—like this leather tassel, which would look perfect dangling from the aforementioned bag.

ASOS Column Dress ($56)

A t-shirt looks incredible under this apron dress, and you can also swap in a button-down shirt for a more polished effect.

ASOS Limited Edition Plaited Headband ($16)

Hear us out: a renaissance of your grade-school headband could be the most stylish thing to happen to your hair.

Zara Perforated Skirt ($80)

Who said perforation was just for athleticwear?

The Mode Collective Point Loafers ($200)

Can’t you picture these cap-toe loafers on cult NYC blogger Danielle Bernstein of We Wore What?

Ganni Skirt ($174)

Matching sets make office dressing a snap.

Rachel Comey Quip Jacket ($515)

The market is awash with black blazers, but this cut stands out from the pack.

Do you have any career advice to share? Let us know in the comments below!

Related Stories