National Boss Day: Empowering Leaders Through Style And Confidence By Jennifer Walderdorff

The 16th of October is National Boss Day, a wonderful occasion to honour and appreciate the leaders who inspire us and drive our workplaces forward. But let’s take it a step further this year by celebrating not just the people in charge but the confidence-building that comes with leadership, symbolized by the way they dress. In this article, Jennifer Walderdorff explores the uplifting and stylish side of leadership, focusing on how dressing like a boss can empower individuals to lead with conviction and flair.


Dress for Success, Lead with Confidence:

Dressing like a boss isn’t just about fashion; it’s about projecting self-assuredness and authenticity. Not just the wardrobe choices can enhance one’s self-esteem, convey a sense of purpose, and foster an environment of empowerment in the workplace. But also the attitude of the wearer emphasizes this impact. And I am not simply referring to corporate basics.

Inspiring Stories of Stylish Leaders:

Angela Merkel:

Angela Merkel, I know what you are thinking, but the former Chancellor of Germany was known for her distinctive style that did not adhere to the traditional corporate dress code. She often opted for colorful blazers, modest dresses, and scarves, which were both practical and reflected her style. Her fashion choices conveyed a sense of individuality while maintaining an image of authority. Her policies, leadership, and maybe her individuality style are what made her the longest-standing Chancellor with 16 years running the show.

Vivienne Westwood:

The late Vivienne Westwood was a British fashion designer known for her unconventional and avant-garde style. While she was not a political or corporate leader in the traditional sense, she was undoubtedly a leader and influential figure in the fashion industry. Her style aligned with her brand’s ethos of rebellion, sustainability, and pushing the boundaries of fashion. She often wore eccentric, punk-inspired outfits with bold prints, unusual silhouettes, and unconventional accessories. Vivienne Westwood’s unique style reflected her leadership in the fashion world and her commitment to expressing her artistic and environmental values through clothing.

Michelle Obama:

While Michelle Obama served as the First Lady of the United States, she became a style icon known for her fashion-forward choices. Her wardrobe featured a mix of designer dresses, casual separates, and statement pieces. She often incorporated vibrant colors and patterns into her outfits, showcasing her fashion flair while breaking away from traditional corporate attire.


Leading Choices of Boss Style

When it comes to wardrobe choices synonymous with leaders, here are three classic styles:

Professional Power Suit:

A well-tailored, classic suit is a timeless choice for leaders. Men often opt for a sharp, two-piece suit in traditional colors like navy, charcoal gray, or black, paired with a crisp dress shirt and tie. Women can choose a tailored trouser suit or a skirt suit, paired with a blouse or a top. This more traditional look exudes authority and professionalism.

Business Casual Elegance:

For a slightly more relaxed yet still authoritative appearance, leaders can choose business casual attire. Men may wear dress slacks or chinos with a dress shirt, perhaps with the sleeves rolled up for a more approachable look. Women can opt for a well-fitted blazer with tailored trousers or a knee-length skirt, paired with a blouse or knit top. This style strikes a balance between professionalism and approachability.

Modern Leadership Chic:

In more contemporary workplaces, leaders may embrace a modern and stylish look. Men can wear slim-fit suits with unconventional colors or patterns, like a well-fitted checkered suit. Women can explore more elaborate blouses, stylish dresses, or mix-and-match separates while maintaining a polished appearance. This style showcases a leader’s ability to adapt to current trends while still commanding respect.

While these are seen as classic examples, when you are your own boss, there are only the guidelines of what you fit into comfortably and makes you look as good as you feel.


Empowerment Through Personal Style:

Dressing like a boss, by no means is an instruction to change what you wear, it is merely enhancing your style, from choosing attire that reflects your individuality to embracing accessories that exude confidence. Dressing like a boss will become a means of self-empowerment, leaving a lasting impact on their professional lives.

Embrace Your Individuality:

Dressing like a boss begins with understanding and celebrating your unique style. Instead of trying to mimic someone else’s wardrobe, focus on clothing that aligns with your personality and preferences. Consider what colors, patterns, and silhouettes make you feel confident and comfortable. Look at your shape and body type to falter and provide maximum comfort. Whether it’s bold and vibrant outfits or classic and understated pieces, choosing attire that reflects your individuality will set you apart and empower you to make a lasting impression in your professional life.

Invest in Quality Pieces:

Quality clothing not only looks better but also lasts longer. When dressing like a boss, invest in well-tailored, high-quality garments that fit you perfectly. A tailored suit, a well-constructed blazer, or a classic pair of leather shoes can elevate your look and exude professionalism. Quality pieces not only enhance your poise but also communicate your attention to detail and commitment to excellence.

Accessorize with Confidence:

Accessories can be the finishing touch that takes your outfit to the next level. Whether it’s a statement watch, a tasteful tie or scarf, or a stylish pair of eyeglasses, carefully chosen accessories can exude self-assurance and personality. Don’t shy away from experimenting with accessories that resonate with you. They can be conversation starters and convey a sense of authority. Just remember that less is often more, so choose a few key accessories that complement your overall look without overwhelming it.


Casual Friday Feeling?

When corporate chic is not an option, and casual Friday or any day is on the agenda – there is a stigma attached to jeans being worn as an alternative. It is data from a study that provides some context to the understanding that jeans are worn when all hope or inspiration is lost on outfit choices. In this study, 51% of women wore jeans when they felt sad, but in contrast, 33% wore them when happy. This just exemplifies the fact that there is no one-size-fits-all-all, and dressing like a boss can ultimately mean exactly what the individual wants it to mean. Whether colour, prints, or plunging necklines make you feel powerful and boss-like, then who is anyone to stand in your way? The beauty of style and being the lead character in the story of your life is that you are writing the script and should be in a place where you can turn up to work how you feel most comfortable because whatever the vocation, career, or title you have earned, you are always the boss of you!


In conclusion, National Boss Day is not just about celebrating leaders; it’s about recognizing the influence of empowerment that comes with leadership. Dressing like a boss is a way to manifest confidence and inspire others. Use your style as a tool for leadership and self-assurance. This National Boss Day, let’s celebrate not just the bosses but the empowering essence of leadership.

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