How to Boss Up While Dressing Down

Two Woman and One Man Looking at the Laptop

Would I rather be feared or loved? Easy, both. I want people to be afraid of how much they love me,

The reason why the TV show “The Office” is so beloved, I believe, is because everyone has met a Michael Scott: a man so into himself while simultaneously trying to win the approval of his peers, that he misses the mark. The type of person who wears a pinstriped suit because they once read in a 2015 issue of “People” that it would make them seem “powerful”. A person who peruses “Cosmo” and learns how to not be the office bitch, rather than learning how to be the office savant. Everyone wants to shrink away from a Michael, but many fall prey to being, well… the office “tool”. So, how do you stay away from a cringe moment while seeming laid back and in control? It’s having the confidence you need to lead, while making everyone else believe it, too.

Photo of Man Holding a Book

Wearing a three-piece suit isn’t cool

*Gasp* Believe it or not, looking like you’re going to prom isn’t what the cool kids are doing. Unless you’re Jack Donaghy in the make-believe land that takes place at 30 Rockefeller Plaza, no one thinks some 1st level manager is hip enough to wear cufflinks. While the homage “Dress for the job you want, not the one you have” isn’t faulty, no one wants to see a mailman in a Batman costume: basically, dress for your job, but add some flair. On a casual Friday, you can forgo the black slacks and nice blouse, but if you want to look like a big wig CEO, show you’re willing to dress for the act without coming off as a pretentious twit. While everyone else is wearing T-shirts with their favorite baseball team on it and a pair of capris, you should be wearing a pair of jeans with a nice button up or blouse. You’re still “casual” while maintaining professionalism, but also “cutting loose”. AKA, “wow” your intended audience without looking like a Dolly Parton rip off – because as Dolly would say “It costs a lot of money to look this cheap.”

This isn’t a Vacay, Bruh

I know some people may think that casual Friday means you should be able to come in wearing your birthday suit or that crop-top your daughter bought you for your 45th birthday, but my god – it does NOT mean that! You need to dress like you are here for a JOB. Imagine seeing your 65-year-old secretary rocking her nighttime neglige. She might feel comfortable and it is as casual as it gets, but you still don’t want to see it, and nor will anyone else. No matter how much of a sexy thing you are, no one should be able to tell the color of your underwear. What I mean is: dress appropriately while also showing your style. I know, this was annoying to hear while you were in school, but, if you wouldn’t want to see your grandma in it: don’t wear it. Chances are, you wouldn’t want to see another colleague – or boss – in a similar outfit.

Photo of Woman Using Her Laptop

This Ain’t the 90s

Sometimes, wearing your favorite band t-shirt can be sort of a liberation movement. You get to relax a bit and show your personality. However, if your favorite “Shin’s” T-shirt has a mustard stain from here to the southern border, you have a problem. I know I seem to contradict myself from my previous point, but a few times a quarter it’s totally cool to show a bit of personality as long as you’re most willing to show you are professional. 

If on a casual Friday you want to wear a nice T-shirt showing a band or a hobby: rock it! If you’re going to a board meeting with a stain on your shirt accompanied by ratty jeans, you aren’t “casual”, you’re a slob. There is no reason that “individuality” has to equal “total mess”. 

If you do choose to wear something more casual, such as a T-shirt, you can always keep it casual while still maintaining an air of business. Wear a nice belt that will make your jeans more polished and a nice-fitting blazer over it. This will make you look stylish while also not making it look like you rolled out of bed. Adding that third piece will bring together your outfit in a clean and professional way.

Man in White Dress Shirt Blue Suspenders and Gray Polka Dotted Bowtie


While having a clean look is always good, there’s no reason that dressing down means you can’t dress up! Sometimes having a clean look (a nice button-down shirt or blouse with pressed slacks) can be exemplified with the right accessories. Slick ties or bow ties for men, or a nice watch can really spice up an outfit. For women, having a nice necklace or scarf can take any outfit up a notch. Even shirts that you’ve worn a thousand times can look completely new if you pair it with new or different accessories. 

Of course, these accessories mean nothing if you look like a total slob. If you are going to bother ironing your slacks, then you should take it upon yourself to make sure you look tidy, too. This means; pulled back or styled hair, well-fitting clothes that compliment your frame, shoes, and socks that match, and a belt to keep everything up.  If you’re wearing casual clothes, you should make sure the rest of you is pulled together in a clean and professional way.

Rock the Look

The most important part of looking like a boss while dressing down is to rock what you’re wearing. Whether you’re in your new ironed blouse or walking down the runway in your fresh new tie, the most important part at the end of the day is to make sure you exude confidence. Even a slob that exudes confidence can make people turn their heads, so imagine peoples reactions to someone who looks like a total boss while also acting like it.

While I could go on and on, my point is that everyone has a chance to mix “I’m a boss and I know it” with “ I’m laid back and accessible”. If you want to be “chill” you also have to be professional. At the end of the day, whatever you are wearing needs to be paired with an air of confidence that will capture a room. A great outfit and that confidence will make you the boss of the room, we promise.

Written by: Lauren Anderson

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