Make the Right Impression: 5 Ways to Dress Like an Entrepreneur

Like it or not, what you wear matters—especially when you want to make a great impression. As an entrepreneur just starting out, you want to be taken seriously by potential business partners, suppliers, investors, and customers. Your look should reflect your personality and your brand, because when people see you for the first time, they will make a snap judgment about you and your company.

Are you wondering how to dress like an entrepreneur? This guide offers five important points to consider when selecting your wardrobe.


Always err on the side of formality. Each day, dress as if you were going to meet with another CEO, or with your most important customers. In such company, you’d want to fit in and feel comfortable. What that means may vary by industry; in many fields, both men and women always look sharp in a business suit with a crisply ironed shirt.

If your industry is more casual, such as an outdoor equipment rental business, you might go for a more business casual look. A good rule of thumb is to dress one notch above your customers—if they wear designer brands, you should too; if they wear T-shirts and jeans, you should wear slacks and polos or blouses.

Whatever look you choose, make sure your clothes are high quality, clean, and free from smudges, snags, and holes. Avoid T-shirts as a general rule, unless they are high quality, match the occasion, and/or include your brand and logo.


Be careful with the colors you choose to wear. Black and blue are both solid choices for men and women: Black is a bold choice that reflects power, while blue portrays calmness and confidence.

Women have more flexibility with color. You might try adding bold colors—red is especially memorable—in your shirt, shoe, and scarf choices alongside more muted corporate hues. Men do best with navy blue and charcoal gray. For men, if you go with a tie, pick something bold and silk, but free of cartoony patterns. Women might choose a lightweight colored blouse. Additionally, a quality fabric can go a long way, creating a look and a fit that create your best look.


If you want to dress like an entrepreneur, the devil is in the details. Both men and women are encouraged to shine their shoes—it adds a touch of class and care to your look, and shows that you are a thorough person who cares about the small things.

Adding classy accessories will complete your look. A fancy watch, custom cufflinks, or bespoke jewelry pieces get you noticed and nod to your brand and personality. Pick belts, shoes, handbags, and other accessories that match to present a professional, memorable image.


You want to be comfortable in your day-to-day work, and part of that is selecting clothing that fits. Men and women should own at least one tailored suit for formal occasions. A straining jacket, too-tight blouse, or baggy pants look sloppy. Increase your confidence in yourself and complete your look with clothing that fits and complements your body. Consult a sales associate for help finding the perfect size for you.


Beyond your clothing, knowing how to dress like an entrepreneur includes your personal grooming. Men and women should keep their haircuts neat, tidy, and styled every day. Men should be shaved or keep their beards trimmed, and women should err on the side of more natural looking makeup and hair colors.

Dressing to impress is one part of acting the part of an entrepreneur. To learn more tips for business owners, register for a Daymond John’s Success Formula event.

Leave a Reply

Your email address will not be published. Required fields are marked *