FOUNDER STYLE: FIVE TABOOS
The freedom to dress without prescribed rules has created a new responsibility: business culture begins with its founder.
For decades, the business dress code served a relatively straightforward purpose: it established a visual distinction between professional and private life. What we wore to the office was not necessarily what we would choose for the weekend. Professional environments had their own expectations, understood through established conventions of tailoring, formality, and appropriateness.
Today, that distinction is increasingly difficult to define.
The traditional suit has gradually lost its status as the universal symbol of professional authority. Remote work, hybrid schedules, flexible corporate cultures, and the growing importance of personal expression have changed how we approach everyday business attire. In many ways, this transformation is positive. Professional identity should not be reduced to a prescribed uniform. Comfort, individuality, and personal style deserve a place in contemporary business culture.
But when formal dress codes disappear, the need for professional judgment does not disappear with them.
Instead, responsibility shifts from established rules to individual decisions. For entrepreneurs who set the tone of their organizations, those decisions carry particular significance.
The Cultural Shift: More Freedom, Less Clarity
The transformation of workplace clothing is no longer simply a fashion observation. A 2025 International Workplace Group study of more than 1,000 American hybrid workers found that only 56% reported having a clearly defined workplace dress code. Two-thirds said their dress codes had become more relaxed in recent years. Yet 78% of respondents wanted guidance on what to wear at work or on professional video calls.
In other words, greater freedom has not necessarily created greater confidence about what constitutes appropriate professional attire.
A September 2026 YouGov survey further demonstrated how differently Americans interpret contemporary workplace clothing. Traditional business garments remain widely accepted, while opinions become considerably more divided over T-shirts, sandals, and shorts.
These findings suggest a transition in which traditional expectations have weakened, but new shared standards have not fully emerged.
The problem is not that people have stopped wearing suits. The problem begins when the distinction between comfort and professional appropriateness is no longer considered.
For a founder, this raises a question that extends beyond personal wardrobe choices: if a company no longer relies on a formal dress code, what establishes its visual culture? The answer cannot be found exclusively in employee guidelines. It begins with the values, expectations, and personal example of those who lead the business.
01. Confusing Casual with Business Casual

One of the most common misunderstandings in contemporary business style is the assumption that business casual simply means wearing ordinary casual clothes to work. But these are not interchangeable concepts.
A hoodie, distressed jeans, an oversized T-shirt, and athletic sneakers may create a perfectly appropriate outfit for private life. That does not automatically make the same combination suitable for a professional meeting.
Business casual maintains a connection to the visual language of business attire, even when traditional formality is reduced. A well-tailored blazer, a thoughtfully chosen shirt, dark jeans without excessive distressing, structured trousers, or refined leather shoes can create an image that feels relaxed without losing its professional character.
The essential distinction is not necessarily the category of clothing. It is the relationship between fit, proportions, construction, fabric, and context. Even sneakers can be appropriate in certain business environments. Equally, a blazer does not automatically make an outfit professional if the styling appears careless or inconsistent.
Business casual is not the absence of formality. It is a considered reduction of formality.
What knitwear can reveal about context

Knitwear makes the distinction especially clear. An oversized patterned sweater or a loose, heavily relaxed knit may be an attractive choice for an informal day, while a fine-gauge sweater layered over a shirt or paired with structured tailoring can move comfortably into business casual. Neither is universally right or wrong; the difference is the professional situation and how thoughtfully the pieces work together.
For founders whose schedules move between informal team interactions, business negotiations, public appearances, and unexpected meetings, a versatile wardrobe should allow those transitions without demanding a new identity for every occasion.
02. Choosing Footwear Without Considering the Business Environment

Footwear is often treated as secondary, yet it can significantly influence the overall level of formality. Consider the difference between metallic platform sandals designed for an evening event and a pair of refined closed-toe shoes. Both may be fashionable, expensive, and beautifully designed. They simply communicate different degrees of formality.
The same is true of men's footwear: leather sandals, casual slides, polished loafers, and classic lace-up shoes serve different purposes. None of these categories is inherently unacceptable in every professional setting. A creative studio, an informal summer gathering, a technology company, and a formal investor meeting can have very different expectations.
The question is whether the footwear supports the occasion. In the 2026 YouGov survey, 54% of Americans considered sandals acceptable for women in office environments, compared with 31% who considered them acceptable for men. Rather than proving one universal rule, the difference shows how cultural expectations shape professional appearance.
Personal preference should be considered alongside professional context. An outfit may be aesthetically appealing without being the most appropriate choice for a particular business situation.
03. Overlooking How Fabrics Behave Throughout the Day

A professional outfit should be evaluated not only when first put on, but also by how it performs through an actual working day. This matters especially when choosing fabrics.
Linen is a beautiful natural material with a distinctive texture and an established place in sophisticated summer wardrobes. Its tendency to crease is part of its character. Yet there is a meaningful difference between the relaxed elegance of a carefully constructed linen garment and clothing that has become excessively wrinkled, distorted, or lost its shape.
The distinction becomes particularly noticeable in tailored clothing. A jacket that no longer holds its structure, trousers heavily creased after sitting, or a shirt that quickly loses its appearance can change the impression of an otherwise carefully selected outfit.
This is not an argument against natural fabrics. It is an argument for understanding their properties before incorporating them into a professional wardrobe. Composition, construction, lining, garment weight, and intended use all matter.
An effective business wardrobe should work with the realities of a person's day, not only with the aesthetics of a photograph.
04. Allowing Clothing Details to Distract from Professional Communication

Transparency, visible underwear, exposed straps, and revealing garment details are often discussed as questions of modesty. I consider them primarily questions of visual communication and context.
Clothing directs attention. The placement of a neckline, the transparency of fabric, a visible undergarment, and even the relationship between socks and tailored trousers can alter where the eye is drawn. In a formal professional environment, these details deserve consideration because they can compete with the intended message.
This does not mean the body should be hidden or individuality sacrificed. Nor does clothing determine someone's competence or integrity. The point is to understand how visual elements interact. A transparent blouse may require a considered underlayer; a fitted garment may need different underwear construction; a neckline suited to an evening occasion may create a different impression during a formal meeting.
These are styling decisions, not moral judgments.
Professional presence becomes more coherent when clothing supports communication rather than unintentionally competing with it.
05. Mistaking Visible Luxury for a Strong Professional Image

Another misconception deserves examination: the belief that expensive or highly recognizable items necessarily strengthen professional appearance. Large logos, prominent belt buckles, glossy accessories, statement watches, heavily branded shoes, and multiple decorative details can all become competing visual signals.
Individually, these elements may be beautifully designed. Together, they can create an image in which attention moves away from the individual and toward the objects. For someone representing a business, this distinction is worth considering.
A strong professional image does not require eliminating luxury, distinctive accessories, or personal taste. It requires understanding visual hierarchy. What should attract attention first: the person, their communication, and their professional presence, or the brands and objects they are wearing?
There is no universal answer for every industry or personality. In creative environments, expressive styling can be part of the professional language. But even expressive styling benefits from intentional composition.
The value of a professional image is not determined by how many recognizable objects it contains, but by how coherently those objects communicate the individual's identity.
Why the Founder Should Set the Standard
These five examples may appear to concern relatively small wardrobe decisions. Together, however, they reveal a broader issue. As professional dress codes become less structured, people increasingly rely on their own understanding of appropriateness, aesthetics, cultural expectations, and professional identity. This creates freedom and responsibility at the same time.
How can a leader establish expectations for the professional appearance of a team without first considering the standards they apply to themselves?
A founder's personal style does not need to become an employee uniform. Imposing one person's aesthetic preferences on an organization would often be counterproductive. But leadership inevitably creates examples.
The way a founder prepares for meetings, presents themselves publicly, communicates with partners, and approaches everyday appearance contributes to the culture experienced by those around them. A company may encourage individuality while maintaining clear professional expectations. A founder may reject traditional corporate attire without rejecting principles of appropriateness and consideration.
The important distinction is between freedom from unnecessary formalities and indifference toward professional context. These are not the same thing.
Beyond the Dress Code: Developing a Personal Standard
In my approach to Founder Style, the objective is not to replace one rigid dress code with another, or to create a standardized image of what an entrepreneur should look like. Everyday style should reflect the person behind the business: identity, professional role, lifestyle, cultural environment, and the situations in which that person regularly appears.
For some, this means a carefully developed business-casual wardrobe. For others, a more formal approach is appropriate. For founders in creative industries, a distinctive and unconventional visual identity may be essential to their presence.
What matters is consistency between the individual, the professional environment, and the impression they intend to communicate. Clothing alone cannot establish leadership, competence, or trustworthiness. It remains, however, one of the visible elements through which professional identity is expressed.
As traditional business dress codes become less influential, personal standards become more important — not less.
Perhaps this is the central challenge of contemporary Founder Style: learning to distinguish between the freedom to wear anything and the ability to choose what is appropriate.
Because professional elegance was never simply about following a dress code. It is also about knowing when, why, and how to make a considered choice.
Further Reading from THE ART OF PRESENCE
Explore how personal style and professional conduct shape a coherent public image in Business Etiquette and Personal Style: The Standards Behind a Professional Image, and why a founder's visual presence should evolve with their professional role in Why Your Personal Image Might Be Lagging Behind Your Professional Success.
Anastasiia Ivanova · THE ART OF PRESENCE · New York
