5 Tips to Dress Like the Cool Boss You Want to Be

If you think dressing down is a recent phenomenon, think again. By 1996, almost three-quarters of Americans had a dress down day in the office. Now that business dress is even more laid back, how does the boss still look like the boss.

Being a cool boss starts with your wardrobe. To communicate the management style you want to project, use these 5 cool boss style tips.

A Cool Boss Wardrobe

A cool boss isn’t just a cool dresser. A cool boss is one whose elegance extends to their management style as well as their dress style.

A cool boss is authentic, consistent and confident. These are qualities that apply to both dress and behavior. And, by the way, they’re gender-neutral too.

1. Blaze a Trail

A blazer is an article of clothing that just works. It says laid back but chic too. In workplaces where business suits are no longer appropriate, a blazer can inject a subtle formality to your look.

Try unlined, softer fabrics but don’t compromise on the quality. A good fit and excellent tailoring say “I’m the boss”, better than having your job title on your name badge.

Partnering a blazer with a T-shirt combines smart and casual really effectively. The T-shirt must be not too tight or too loose. Choose a T-shirt fabric that keeps its shape well.

2. Suits You

There are times when a suit is the right thing to wear. Certain meetings with clients, formal business occasions and the boss of the year awards all call for a suit. It’s cool to know when a suit is appropriate.

Combining smart with casual can look especially confident. And guys, leave the tie off, but keep it in your pocket. Being prepared, in case you’ve miss calculated, is also cool.

3. Wear Sneakers

Wearing a suit with sneakers is no longer a business dress faux-pas. Wear them with jeans, chinos or even a suit. They say you’re cool and confident enough not to have to wear the standard office footwear.

Sneakers can look relaxed but they don’t have to be the scruffy ones you wear when shooting hoops in the yard. Shop the collection at SSENSE for designer credibility. 

4. Watch It

You can be in jeans and a T-shirt but wearing an iconic watch will set you apart from the crowd. Wear Rolex, Breitling, or TAG Heuer. These are among the brands that will mark you out as a leader with style. 

5. Not Just Any Chinos

Chinos are the smart casual go-to for office apparel. Take a look around the office and you’ll see every other person wearing them. How do you stand out in these ubiquitous symbols of the modern casual business person?

The trick is to wear chinos with a difference. Chinos, made with a little extra care, say you’re relaxed but cool too. A waistband that is finished like proper trousers, better quality cotton twill and a fine belt make you look like the boss.  

Be Cool

Having a cool boss makes the office a great place to be. Set the tone with your dress style and back it up with your behavior. Be cool.

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