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Celebrate Boss’s Day with professional flair

2 business women talking in hallway

Monday, October 17 is Boss’s Day – a day reserved for employees to show appreciation to their superiors and strengthen the bond between officemates. Whether you’re the boss in your office or you work on a team of colleagues whom you appreciate, there’s no doubt that there are professional women who inspire you – and many of them are stylish!

Many struggle with finding professional clothes for women that aren’t too stuffy or too sexy. Here are some of the most stylish ladies in power and how you can draw inspiration not only from their accomplishments, but also their workwear.

Sheryl Sandberg

Sheryl Sandberg was the first woman to serve on Facebook’s board, and is now the Chief Operating Officer of the social media giant. In addition holding such a high title of one of the biggest websites in modern times, she’s also an activist for women’s rights. Sandberg founded the Lean In Foundation in 2013, which focuses on offering women inspiration to help them achieve their goals in the workplace. Her book, “Lean In: Women, Work and the Will to Lead,” was also written in 2013 as a guide for professional women working their way up the corporate ladder.

Sandberg manages to have one of the fullest calendars in the professional world, while still dressing amazingly. With a fondness for short and long sleeve sheath dresses, her office outfit is on point at all times. If you’re looking to emulate this style, take a page from Sandberg’s book and pair your favorite sleeveless dress that you wear in the summer with a fashionable one button blazer for the fall.

Anna Wintour takes professionalism and makes it fashionable.
Anna Wintour takes professionalism and makes it fashionable.

Anna Wintour

You can’t even think about fashion without the name Anna Wintour popping into your head. This journalist started off as one of the first editorial assistants at Harper’s Bazaar UK and paved her way to becoming the editor-in-chief of Vogue. She’s held this position since 1988 and has become as much of an icon in the fashion world as the models that grace the pages of the magazine. Though there are rumors that the notorious Miranda Priestly of “The Devil Wears Prada,” is based on Wintour, this hasn’t stopped her from being one of the most respected and revered women in the fashion and journalism industries.

Although we don’t all have the cash to deck ourselves out in runway duds, that doesn’t mean we can’t learn a thing or two from Wintour’s fabulously funky style. From faux fur vests to those sky high dress heels you’ve been hesitant to wear, bust out anything that’s been sitting in your closet for being too out-of-the-ordinary and rock it in true Vogue fashion. Another way to draw inspiration from Wintour is to never forget to top your outfit off with a statement necklace.

“Tie a look like Nooyi’s together with high heel pumps.”

Indra Nooyi

Indra Nooyi started at PepsiCo in 1994 as the Senior Vice President of Strategic Planning, and worked her way up through multiple positions until eventually taking on the title of Chairman and Chief Executive Officer in 2007 and 2006. She’s been included on Forbes’ World’s 100 Most Powerful Women year after year and served on a variety of boards, from the U.S.-India Business Council to the World Economic Forum.

Nooyi has a very classic professional look, complete with chic skirt suits and pearl necklaces. If you work in a law office or other conservative setting, or just want to channel an “I’m here and in charge” sort of vibe with your office outfit, Nooyi is the woman to look up to. Tie this look together with high heel pumps and a tailored satchel for all of your work documents.

Marissa Mayer

A traditional boy’s club, the tech industry is no stranger to Marissa Mayer. Before taking on the role of president and CEO of Yahoo in 2012, Mayer was an executive and spokesperson for Google. In addition to holding such a high position with Yahoo, she’s also an investor in a variety of companies, from decor site One Kings Lane to startups like uBeam. Mayer is truly a multifaceted professional, with her hands in a variety of industries. As if all of this isn’t enough to fill a resume to the brim, Mayer is also a board member of the New York and San Francisco Ballets – she was a dancer when she was younger – and the San Francisco of Museum and Modern Art.

Mayer has learned how to balance professional attire with classically feminine pieces to make for a very well put-together office wardrobe. Mixing full skirts and floral blouses with neutral dresses and cardigans, Mayer proves that there’s no need to sacrifice style and function for a professional look. Channel this look all year round by not saving your florals just for spring and wearing your dresses with tights or hose in the cooler months.

The women referenced in this article are not associated with or endorsing Monroe and Main.

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