» Subject: Gary Chun, Star-Advertiser entertainment writer
» Reason: After 30 years, he’s aged out of his 1980s roadie uniform of graphic music tee
» Goal: A more mature, stylish look
» Clothes: 21Men

While attending December’s grand opening of Forever21, I sent out tweets about the lines and merchandise and was surprised when co-worker Gary Chun responded, "My T-shirt years might be ending. Gotta work on the wardrobe. Wanna help?"

It’s not every day a man volunteers to be a fashion guinea pig, so I was game for a makeover. In Chun’s case, he’s been dressing in the same uniform of graphic tee and slacks or denim since he was in his 20s.

His parents never imposed any dress formalities, and it was only while attending Saint Louis High School that he wore dress shirts. All that went out the window once he attended the University of Hawaii, where he was drawn to music writing.

Wearing T-shirts, he said, "started with my love of music. It was one way to find a like audience, and it was also a way to show my appreciation of anything well conceived and well designed."

Now in his 50s, he said he’s starting to feel dated when interviewing young musicians who, even when aiming for intentional shabby looks, are styled and sophisticated in dress. Raised in front of a camera and accustomed to preening before a social media audience, no one under 30 would dream of going out underdressed when digital paparazzi are everywhere, and we all live in fear of the "fugly" tagged photo.

So, Chun figured it was time to grow up. That doesn’t means dressing old; it just means being contemporary and adapting to the ’00s instead of looking like someone whose mindset reads 1980s or earlier.

There’s nothing wrong with graphic tees, which are more popular than ever due to such websites as Cafe Press and Threadless, which expand access to artists’ creations around the globe, but there are ways to add a little more polish to Chun’s basic look, which he describes as minimalist.

"When I was younger I could get away with a lot more pattern, but these days I prefer graphics that are a little less exaggerated, more refined. I don’t like the design to be all over my T-shirt."

The T-shirts worked for him for a long time because they are a way of communicating with kindred souls. In the beginning he started with shirts that showed solidarity with his favorite bands, and he connected with fellow music lovers that way. Over the years the various messages on his shirts would often serve as a sort of social experiment to gauge individuals’ responses to opinions he would otherwise not voice. They would often spark conversations with strangers. It’s really a more literal process than what fashion people do all the time, which is read others as expressed through their clothing.

We gave Chun two looks, a classic and a casual, both from 21Men. A dress shirt and black cardigan would work on days that might include a lunch or dinner interview. For more informal occasions, we gave him the option of a comfy, lightweight striped knit shirt ($12.90) that can be worn under a lightweight, hooded utility jacket ($37.90) that might also double as a raincoat. He could swap the shirt for any of his graphic tees to bring out his personality. Additionally, he could pick up a sport coat to wear over a dress shirt or T-shirt and look appropriate, and better dressed than most, at almost any Hawaii occasion.

For both Chun and our other makeover subject, Taizo Braden, it’s a start, but one word of caution: Women do love a sharp-dressed man, but not if he cares about fashion more than us.