What’s "Work Appropriate"? Managing Generational Expectations

In today’s multi-generational workplaces, dress codes are as varied as music tastes, from ‘90s R&B to today’s viral TikTok anthems. And nothing sparks debate faster than the phrase, “Back in my day.”

A consultant I spoke with built their career when traditional business attire was a mark of respect. A sharp suit, polished shoes, and a structured blazer were nonnegotiable. As they put it, “If someone showed up in joggers and flip-flops, I wouldn’t take them seriously.”

But times have changed. According to Forbes, 58% of employees now prefer business casual, casual, or no dress code at all. Forbes

I saw this shift firsthand during my 15 years in finance. The bank I worked for provided every employee with a uniform consisting of navy suits, white button-downs, and black heels. After five years of the same look, everyone, including me, was over it. So I joined the dress code committee and quickly realized something. The people deciding what was “appropriate” all came from the same generation, with the same set of expectations.

Workwear is more than just clothing. It reflects values, culture, and identity—each shaped by the era in which we entered the workforce.

Generational Approaches to Work Attire

Traditionalists & Baby Boomers: The Power of Formality

For older generations, dressing for work meant structured suits, ties, pantyhose, and polished shoes. Every day. No exceptions. To them, formal attire equates to professionalism, discipline, and respect.

Gen X: The Casual Friday Pioneers

As Gen Xers climbed the corporate ladder, they introduced a more relaxed approach, pioneering the business casual movement. They remember when Casual Fridays first emerged and still appreciate a polished look. Think tailored blazers and slacks with more flexibility than their predecessors.

Millennials: Breaking the Mold

Millennials, who entered the workforce alongside the rise of tech startups, questioned the need for rigid dress codes altogether. With companies like Google normalizing jeans, hoodies, and sneakers in corporate settings, workplace fashion evolved into a space for personal expression. For them, comfort and productivity go hand in hand.

Gen Z: The Authenticity Advocates

Gen Z, the newest group in the workforce, grew up in an era of remote learning, influencer culture, and fluid self-expression. They see no issue in blending casual and professional styles. To many in this generation, yoga pants and Converse sneakers count as business casual as long as they are clean and intentional.

As Kourtlynn Faith shared on TikTok, “Gen Z isn’t spending money on work clothes. It’s either work clothes or clothes to go out. There is no in-between.”

Strategies for a Cohesive Workplace Dress Code

1. Create a Clear but Flexible Dress Code

Instead of rigid, one-size-fits-all policies, companies should define clear expectations while allowing room for individual expression. This means setting guidelines based on the company’s brand, client interactions, and industry standards rather than outdated traditions. Using a spectrum approach such as client-facing business, business casual, and creative professional helps employees navigate dressing expectations without feeling restricted.

2. Encourage Leadership to Set the Tone

Employees often look to leadership for cues on what is acceptable. Having leaders across generations embody the dress expectations of the company without making it feel forced helps normalize modern interpretations of professional attire.

3. Offer Workplace Styling & Image Workshops

Partnering with experts, like myself to host workshops on personal branding, dressing for influence, and navigating workplace attire can help employees across all generations understand how to align their wardrobe choices with their career goals. This turns dress codes from a rulebook into a strategic tool for self-presentation.

Finding the Middle Ground

Saying, “This is how we’ve always dressed,” no longer works in the 21st-century workplace. Dress codes should evolve to support company growth, industry trends, and employee engagement. The goal isn’t to force a single style but to create a work environment where every employee, regardless of generation, feels confident, respected, and ready to show up as their best selves.

Who Am I?

I help mid-career leaders and young professionals strategically enhance their presence and build trust and influence. I offer concierge styling services and corporate workshops focused on building an authentic professional image and distinct personal brand.?

Ways we can work together

1. Book a workshop for your organization: Complete the speaker request form
2. If you're unsure how to dress for your workplace, now is the perfect time to book a Virtual Style Shift Session with me for $197.