Starting Your First Job? Here's Your Corporate Dressing Starter Pack

For serving looks from 9-5.

Model wearing a gray blazer and matching skirt.

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It’s been a while since I stepped into an office. As a writer—a fashion writer, at that—my work-from-home outfits generally consist of a rotating wardrobe of floral printed dresses, overalls, and men's suits. Think creative freedom with zero dress code. It just so happens that my little sister, age 20, and I are starting jobs two blocks from each other in New York City this summer. When she came to me for wardrobe advice, an honor of the highest power as an older sister, I started making a list. That list became this piece.

I thought long and hard back to my first job out of college in the city, which also started in the hot summer months. I didn’t have the financial means to stock a whole new wardrobe, and believe me, my literal wardrobe could barely afford the additions. I tried to focus on a few key pieces in neutrals like black or navy that I knew I’d wear forever. As I dust off some of them today, four years later, I love that they’ve not only stood the test of time, but proven themselves as sound investments. Read on for the seven categories I think every new-to-the-workforce person should consider. Shop your own closet first: “Borrow” from your older sister, if you’re lucky enough to have one, take a day and shop vintage, and then shop these picks for a closet you’ll love as much as your hard-earned PTO.

Dressed Up T-Shirt

Here’s a trick I wish someone would have taught me earlier in my career. A T-shirt, when worn properly, is a fantastic warm-weather work staple. There are a few things to be sure of. First, this isn’t the T-shirt you pull over a wet swimsuit on your way back to the train. This T-shirt should be structured in some sense, either a solid collar or a thicker fabric. It should be one color or striped. Wear it tucked into your favorite trousers or with a simple skirt for a no-brainer outfit. Layer a few simple necklaces or opt for statement earrings. However you spin it, this workhorse is guaranteed to make getting dressed way easier.


When I was in college, the “trousers'' that were in style looked a lot more like stretchy black cigarette pants. Not thanks. It’s the Golden Age of trousers now, and you don’t even have to commit to sourcing a vintage pair. Lots of new brands are killing the wide leg, relaxed trouser look. Try pairing with the aforementioned T-shirt or a matching oversized blazer for that Scandi look we’re all hoping to stumble into.

When in doubt, a little bigger will always feel better than too tight. According to Beverly Osemwenkhae aka BeverlyO, wardrobe stylist and founder of ProjectBee Consulting, fit and quality make for a great trouser. “There are so many different cuts and pants styles, but what really makes a great piece is the way it fits,” she says. “If a pant fits proportionally with waist to hip ratio it's a keeper, and if it enhances all your best features it's a plus.”


Like a clean, crisp white T-shirt, a solid pair of white sneakers also belongs in any work wardrobe. But for days when you need to level up a little, it’s great to have a go-to shoe style that’s not a heel or a sneaker, but somewhere in between. The choice is incredibly personal. Beverly loves a closed toe mule, which she calls “a little more elevated than wearing a ballet flat and also just as comfortable.” My personal preference is a loafer. Investing in a material that wears well, like leather or a thick sole, means this purchase will last long after your internship is done. Try not to get distracted by hyper-trendy cheap shoes. You’ll just end up replacing them in a few months.

Work Bag

In a similar vein, only you know what you need out of a work bag. And it might make sense to hold off until you’ve had a few days on the job to know what you’re really asking of a tote. Carrying a laptop to and from the office? Working mostly from home? Once you’ve decided what’s important, be sure to keep a smaller pouch inside filled with essentials so that when you’re desperate, you don’t have to dig through your entire bag. If the pouch feels too high maintenance, then opt for a bag that comes with built-in storage.


Nothing says “hard at work” like a blazer. Similarly to trousers, always size up when in doubt. Wear your blazer over a summer dress that’s maybe more appropriate for happy hour. Pair it with a pair of Bermuda shorts or keep it simple with matching pants. You really only need a few blazers to transform your wardrobe.

Black Dress

“I just found a midi shift dress so chic. It can be styled in so many ways,” says Beverly. Now’s the chance to dust off the little black dress your mom made sure you packed for college. Feel free to let your personality shine through, AKA the dresses you wear don’t have to feel too corporate. These three picks are a perfect example of three different interpretations of a little black dress that’s great for the office. You’ll get a sense after the first few days of what flies in the office and what you should save for the weekend.

Midi Skirt

If pencil skirts are 2014, then midi slip skirts are 2022. They’re a dream come true for those looking to keep things breathable without having to wear something skintight. Try pairing any of these skirts with a sleek white T-shirt, a button up, or a cropped cardigan if the office AC runs cold (and let's be honest, it almost always does). In the fall and winter, you’ll love the option of pairing these with boots and bodysuits. 

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