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The Blog

Approachable inspiration for a stylish life. 


How to Dress Like a Boss in a Dressed-Down World

Kristen Berry

Faux Fancy_How to Dress Like a Boss

While watching an episode of “Mad Men” or “House of Cards,” I’ll often catch myself wishing that I could wear such exquisitely beautiful, formal clothes to work without feeling woefully, awkwardly overdressed.

This frustrated me when I first moved to the Bay Area from Metro Detroit. While we dressed casually at the office of the PR agency I worked for in Michigan, when we had a client meeting or a new business pitch, we dressed up. And I did so gladly. I love dressing up. I like wearing “work clothes” to the office. It makes me feel fashionable and professional and ready to kick the day’s ass.

So when my California supervisor sat me down ahead of a big client meeting and suggested I dress less “nice,” I bristled a bit. But while your ideas, intelligence and work product are the most important things at the end of the day, it’s naive to think that what you wear doesn’t matter. Here in the Silicon Valley, well known for its acceptance of hoodies and flip-flops in the workplace, dressing overly formally can do more than just make you look out of place – it can give the impression that you’re out of touch, too stiff or just not the right fit for a company’s culture, especially if you’re already an outsider.

But in today’s casual culture, what exactly are you supposed to wear when you have a big meeting, a job interview, want to show your boss (or employees) that you mean business, or just want to step up your workplace fashion game? And how can you balance looking appropriate while maintaining your personal style? Here are a few tips and tricks that have worked for me.

Classic Cuts in Bold Colors and Patterns – My Foolproof Recipe

Faux Fancy_Dress Like a Boss_Kristen Berry

When someone recently asked me what I feel most powerful in, this dress immediately popped into my mind. I love the combination of the classic, formal cut and the fun, bold, can’t-miss-me color. This has been my go-to formula as I rebuilt my work wardrobe for the Bay Area. I always keep an eye out for classic office-appropriate clothing staples – structured dresses, blazers, pencil skirts, etc. – in hues and prints that are anything but corporate.

It also helps to mix and match dressier pieces with more casual items, especially for everyday wear. Want to tone down that sharp pencil skirt? Pair it with a cotton tee. Throw a denim jacket over that conservatively-cut dress. Combine your elegant blouse with your favorite jeans. Finding the right mix can create the ideal balance of formality and ease – and get even more mileage out of the pieces already in your closet.

How I recently styled a wool pencil skirt from J.Crew for the office.

How I recently styled a wool pencil skirt from J.Crew for the office.

How to Amp Up Your Wardrobe If You Gravitate Toward the Casual

No matter how beautiful an item of clothing might be, you’re never going to feel confident in it if you’re uncomfortable in it. That goes for physical comfort (Too tight? Too restricting? Too hot or itchy? Don’t buy it), as well as a sense of authenticity. If the outfit doesn’t feel like you (or the you you want to project), you’re not going to feel like your best, most confident self.

First, let’s tackle items that are physically comfortable as well as professional. What are the items you typically gravitate toward, and how can you kick them up a notch? If you frequently reach for t-shirts, keep reaching for t-shirts! However, look for options with an interesting cut or bit of detail that dresses them up a bit. Or just throw a jacket on top – a little topper can make you look instantly pulled together. Also, consider tossing a top or two into the mix that isn’t a t-shirt. A button-down or blouse can feel equally comfortable if you pick one in a breathable fabric that feels good against the skin.

Similarly, if you’d like to add a few skirts or dresses to your work wardrobe, opt for flattering, forgiving cuts (a good A-line works on everyone) in fabrics that allow you to move freely. Also, materials with a hint of stretch tend to be more wrinkle-resistant, in addition to helping you feel more mobile. If you love wearing jeans seven days a week, wear ‘em! Just consider their color, fit, and condition. While light denim is in, a pair of neat, dark, straight-legged or slightly boot-cut jeans go a long way toward looking office-appropriate. Speaking of color, why not branch out of your everyday blues and grab a pair in a different hue once in awhile? And when it comes to shoes, don’t feel pressured to wear heels if they just aren’t your jam. Ballet flats, ankle boots and structured flat sandals work just fine.

1) Emmanuelle Alt; 2) Desiree Rogers; 3) Claire Mazur and Erica Cerulo; 4) Tracy Sun; 5) June Ambrose; 6) Mellody Hobson; 7) Amal Clooney; 8) Emmanuelle Alt; 9) June Ambrose; 10) Amal Clooney; 11) Hillary Kerr and Katherine Power.

1) Emmanuelle Alt; 2) Desiree Rogers; 3) Claire Mazur and Erica Cerulo; 4) Tracy Sun; 5) June Ambrose; 6) Mellody Hobson; 7) Amal Clooney; 8) Emmanuelle Alt; 9) June Ambrose; 10) Amal Clooney; 11) Hillary Kerr and Katherine Power.

Now, for the trickier part – finding a style that feels authentic to you while also presenting a professional image.  Ironically, I find it helps to start by looking at the style of women I admire for inspiration. I ask myself what it is about a certain outfit that speaks to me. Perhaps it’s how crisp Emmanuelle Alt, editor in chief at Vogue Paris, always looks in her blazers. Or the cut of the long-sleeved, boldly printed dress Mellody Hobson, president of Ariel Investments (and Chair of the Board of Directors of DreamWorks Animation) is wearing above. I then make a note (literally, there’s a note in my iPhone dedicated to fashion) to keep an eye out for those things the next time I hit the stores. This also helps ensure that when I walk into H&M or Zara, I don’t walk out with purchases annoyingly similar to items I already have, but pieces that really make a difference in my wardrobe.

What item in your closet makes you feel most like a boss?

- Kristen