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How to Dress Like a Man



Some think style is something you are born with. Joshua Dean, a 28-year-old Bethany Beach native, believes it can evolve—with the proper tools.

A partner in Tom James Company, the world’s largest manufacturer and retailer of custom clothing, Dean thought little of fashion until recently. Now he’s advising some of the biggest men in the media.

His clients range from lawyers to professional football players. “Gino Gradkowski (UD grad who plays center for the Carolina Panthers) is a big client of ours,” says Dean. You will see plenty of pictures of Dean with Craig Conover, one of the stars of the hit Bravo series “Southern Charm,” all over social media. (The two have been friends since they were 6.) He also met producer and talk show host Andy Cohen last year during the taping of “Watch What Happens Live.” “I gave Andy my card, and the next day I had an email from him,” Dean says. He has since assembled a couple outfits for Cohen. 

Growing up, fashion was the last thing on his mind. Dean, a centerfielder for the University of Delaware baseball team, thought mainly about playing in the major leagues. Until he tore a ligament in his elbow.

“I was bitter about how baseball ended for me,” says Dean. With his future up in the air, a friend recommended he interview for a sales position in New York.

He met with Heather Mielcarz, executive sales leader for Tom James. Mielcarz hired him for his accountability—not for his interview clothing. “I didn’t even wear a tie,” Dean says. “I actually did not know how to tie a tie the first month working for Tom James.” He also admits to owning 75 pairs of Nikes, but not a single suit.  

The job humbled him quickly. “I learned that what you wear really affects your confidence,” he says. “Everyone in my office looked very put together, and I was not. I realized this wasn’t baseball anymore.”

He no longer sports the Nikes. Instead, he prefers a pair of Ferragamos. “I would describe my style as charming and sharp but well put together. But fit is everything,” he says.

No matter who Dean is trying to help, his fashion advice is unequivocal. “Find a tailor. Your clothing can make you look 20 pounds heavier if it doesn’t fit properly,” he says. “Get something that is going to last you for 10 years. Buy some properly fitted jeans, a fitted blazer and have a strong shoe rotation.”

Josh Dean’s 7 Tips for Being a Sharp-Dressed Man


1. Fit is everything.

A proper fit can help you look 15 pounds lighter. A custom suit can help you look longer and leaner and feel comfortable. You wouldn’t put a couch in your house that was 2 feet larger than your room allows, so why wear a suit with that same mentality? 

2. Don’t follow every trend. 

Start with your basics: a few pairs of well-fitted jeans, dress slacks and cotton pants. Leave the khakis on the rack. With so many colors, there is no need to dress for a safari. 

3. Style your shirts like you would style your home. 

Start soft and add pops of color as you progress. Keep your white shirts white, then add in  a few shades of blue, a few textures, small patterns or soft stripes. Skip the dark solids. Ditch the shirts that appear to require batteries.

4. Pay attention to your shoes.

They say a lot without ever saying a word. Many people don’t make eye contact, which means the first impression they have of you comes from your footwear. At work, keep them classy and appropriate—no more square-toed dress shoes. When you go casual, try a suede Chukka. 

5. It’s T-shirt time.

Whether you prefer V-necks, crews, henleys or scoop necks, be mindful that less is more. Find materials that feel good and styles that fit well and give you confidence.

6. Denim decoded.

Wear jeans that make you look good. They should break about one inch or less over your shoes. They should fit your waist. Big thighs? Find a jean with some stretch. Explore a few different shades of denim, too, from dark blue to gray. Avoid big logos.

7. How you treat anything is how you treat everything. 

After you wear your shoes, insert cedar shoe trees. They triple the life of your shoes by soaking up leftover moisture and preventing premature creasing. Pants should be hung from the bottom, not the middle. Let gravity be your iron.  

Josh Dean is a partner in Tom James Company, the world’s largest manufacturer and retailer of custom clothing.//Photo by Laura Schale

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