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  • Dean Birinyi

Dressing for Success

"What should I wear for my headshots?" The answer is to wear things you love.

Below is an excerpt from my Executive Headshot Success Guide. This is the introduction to the section on dressing for your headshots. You can read the entire Guide online or download each article individually by following this link.

Combining style with professionalism

Executives must be prepared to present different aspects of their personalities to suit the culture of diverse workplaces and match the tone of a particular event.

Express yourself

The first rule of dressing well for your headshots is to be comfortable in whatever you’re wearing. The second is that your clothes need to fit you, and the third is to express yourself.

Dress comfortably but well

In an instant, the clothes you wear communicate your social status nonverbally to everyone. A Silicon Valley executive is expected to wear a suit jacket over a t-shirt or an open-collared shirt but no tie. The jacket may be from a $2000 suit and the t-shirt from Lululemon, while an engineer for a startup is expected to wear a hoodie.

The relaxed standards of formality that are common in the Tech Industry do not always apply to women. Even when projecting an air of casual competence, female executives are expected to present themselves more effectively than men.


Bring too many outfits to your shoot, consult with your photographer about what works best for you. Suits and ties are great. If you wear sweaters, turtlenecks, t-shirts, bring them, or whatever clothes you feel most comfortable in at work.

I advise women not to wear sleeveless tops unless they’re under a jacket or sweater for two reasons. The first is that your bare upper arm will compete for attention with your face because it’s about the same size as your face. The second is that it’s a very casual look that could undermine your authority. Talk with your photographer about how it works for your unique look.


Whether you’re a man or a woman, wear shirts with a neckline that mirrors your jawline because it enhances your natural attributes. If you have a sharply tapered jawline, a V-neck will look great, whereas a rounded chin will be enhanced by the smooth curve of a crew neck.

Women should wear whatever depth of neckline they’re comfortable within the workplace. The deeper the neckline, the more critical it is to select the right necklace. Bring several options and work with your photographer to craft your look specifically for each outfit.

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