Style Inspiration: What to Wear As A Young, Stylish Boss

Kirah writes,” At 27, I have recently been given a biiiig promotion. My new post requires me to be constantly in the public eye, in the media, and having meetings with VIPs (including ministers and ambassadors) who are much older than me. I want to strike the perfect balance between looking like a boss (because I am the boss of people who are my parent’s age) and looking like the young, fashionable 27-year-old that I am. Any ideas?”

Congrats on your promotion, Kirah! Big tings a gwan. At any rate, Jihan and I collaborated on a few ideas. You ready?
Just because you’re a boss doesn’t mean your wardrobe has to lose all the fun! Play a bit with pattern while sticking to conservative silhouettes. I love this graphic print dogtooth print pencil skirt and top by McQ by Alexander McQueen:

Play down the patterns with a black blazer and black pumps, but continue to pop with a red bag. This might seem like a lot of look, but you can mix and match each item with different pieces in your wardrobe to create multiple work ready ensembles. Pair the skirt with a white button down; wear the top with black pants; rock the black jacket, black pumps, or red bag with just about anything:

If all over pattern is too much, you can also have a bit of fun with a classic. Instead of a hum drum black jacket, try a striped beaut, like this one by Vivienne Westwood.

Of course tone it all down with a black pencil skirt and heels, along with a statement bag (the one pictured above is from Louis Vuitton):

My last look comprises a Black Halo dress in burgundy, anchored by brown Christian Louboutin pumps:

Accent with small statement earrings, and throw on a trench and a Chanel bag on your way to and from the office:

Jihan says, “You get those coins and prestige, girl! If you want to look like a boss, the first rule is: dress like a professional. Look for pieces with modest, classic silhouettes. It makes for easier dressing and of course, you’ll look like the authority figure you are. Since you’ll be in the public eye, take a cues from First Lady Michelle Obama, and look for eye catching, layerable pieces. This Akris dress is a good foundation. It’s feminine yet commanding. Round it out with a blazer and pair of power pumps.”

“… Make your statement with accessories, particularly a chic statement necklace, which will go further than say, a statement earring. Other than that, keep the rest of your look simple. Splurge on a well-structured boss lady-worthy bag. Looking for the necklace pictured above? Get it here. The navy version of the blazer is here.”

If you’re going to wear pants to the office, make sure they’re work-approved, well-cut trousers. Peplums are all the rage this season, so if you want to stay on trend, find a top with a modest peplum in, again, a timeless silhouette. The neon necklace is another trendy piece that will work in the office if you pair it with the right outfit.”

“… Add a red lip, some colorful shoes, and voila! You look like a boss, and don’t have to give up your youthful style. You can get the green version of the shoes pictured here, and the peplum top here.”

Get some affordable options here:

And there you have it! Which look would you rock?
And how do you dress with authority while staying stylish?

See more of our Work Wardrobe tips here.


Claire Sulmers is the publisher and founder of Fashion Bomb Daily, the #43 most influential style magazine in the world.

  • Instagram

  • Shares