If you met Sam Pizzo today, there wouldn’t be any doubt that he’s a well-dressed man. As a Sales Consultant and Team Leader for Tom James, one of the oldest manufacturers of custom suits out there, it stands to reason that he’s got to look good. When we sat down to talk about everything from style to life goals, we didn’t expect to learn more about Sam’s own personal style journey, but we sure are glad we did.

Setting the Scene

Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.
Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.

The top floor lounge of Sam’s apartment building was a study in modern comfort. Large glass windows looked out over Chicago’s impressive skyline as natural light streamed over the contemporary seating arrangements and bar. Our voices echoed slightly as we chose our seats and sat down to talk.

Sam’s blue pinstripe suit and light purple shirt complimented each other nicely, especially now that the bright surroundings highlighted the richness of their color. Little details like a patterned pocket square and nice watch made it clear that he really knew how to dress.

Whenever I meet people this put together I usually expect them to have possessed those style senses their entire lives. When a person looks like they’ve got it all figured out, the final image is so pristine that it’s difficult to see the work that gets put into it. Everybody cultivates their taste as they get older, and it makes sense for people to learn style just like they learn everything else.

In the Beginning, There Was . . .

Photos of Sam Pizzo before he worked for Tom James. Photos provided by Sam himself.
Photos of Sam Pizzo before he worked for Tom James. Photos provided by Sam himself.

To learn more about Sam’s own style journey, we started by looking back on some of his older dressing habits.

Can you tell us anything about college age Sam? Did he dress well?

“I always thought I dressed well but now I look back and see that I really didn’t know what I was doing. . . I wore some bad Affliction and Ed Hardy bejeweled graphic tees. I had stud earrings and wore Von Dutch trucker hats. Outfits were made up of acid wash jeans 3 sizes too big with shirts that were 3 sizes too small. In retrospect, I had no clue. At the time I was just I was following trends.”

Wow, how did those choices come about?

“If you were to look back at it, I look like a total joke. But at the time it was in fashion. If you were to go out to a bar in East Lansing and you weren’t wearing something from Ed Hardy or Affliction, you didn’t know what you were doing.”

It’s kind of comforting to know that even those of us who look the most polished have made a few fashion missteps along the way. I for one may or may not have worn tie-dye tee-shirts and old sports shorts to class during my freshman and sophomore years. I may have even refused to buy new shoes until I had worn multiple holes in the pair I already owned.

This is all rumors and hearsay, of course, there’s no photo evidence of such travesties ever occurring. I’ve made sure of it. I’m sure everybody reading this has at least one past fashion choice that makes them cringe a little. We all start off a little ignorant of fashion, and that’s OK. What matters is that we learn as we mature, like Sam.

Upping Your Game

Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.
Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.

When you set out to start changing your style, it’s good to find a place to start. Usually, this is where a style role model comes in. It’s important to find someone whose way of dressing appeals to the person you want to be. It can be a character on a TV Show, a celebrity or even a friend. Here at GREY, we’re looking at Sam, not only because he’s on top of men’s fashion, but also because he worked hard to get there.

When did you eventually change your mind about dressing?

“Things changed when I started working for Tom James. As I mentioned earlier I had no idea what I was doing before I was hired.  You should see some of the suits I would wear for interviews. They were way too big for me and way out of style.”

Was your style immediately changed when you started working there or did it take time?

“When I started at Tom James, suits were so much looser and baggier. I remember there was a guy in our office who dressed the way we do today, trim jackets with pants and shirts that actually fit and accentuated the body. I was like, “Dude what are you wearing? That is way too tight! I can see your thigh – I can see your butt in those pants”. I was really traditional and told myself that I’d never dress like him.”

Sam Pizzo photographed by Madeleine Hettich
Sam Pizzo photographed by Madeleine Hettich
Well obviously your style has changed since then, what was that like? Did it happen all at once?

“My style has evolved pretty steadily since my first day at Tom James. I went from wearing a ton of solids and basic striped suits to what I wear today. A few years ago I started incorporating plaids into my outfits, I started wearing sports coat suit combinations where I could break the suit up. Then I started developing alternative fall/winter looks where I would wear a custom sweater instead of a custom shirt . . . Then it got to the point that in the summer I stopped wearing a tie to work if I didn’t have to. Instead, I would choose a short-sleeved polo that was silk or linen under a sports coat with linen slacks so I was working with different textures.”

Now that you’ve reached your current point, what’s it like to get dressed in the morning?

“Now I think I do all of that, just depending on the day. I go from one day where I look like I could be an investment banker, and the next day I look like I could be working in Silicon Valley. I want that because I want to be able to work with all types of people and show them that it can all still be from one company or styled by one mind (which is me). So versatility is key. Dress to your audience.”

To be able to consciously create your personal image is a skill, and skills can be learned. We all start off shaky when it comes to style and fashion, but if you set out to develop your taste you can learn to dress in a way that lets people see you for who you know you are.

And the Moral of the Story is. . .

Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.
Sam Pizzo poses in front of a Chicago skyline. Photographed by Madeleine Hettich.

When all is said and done, not everyone grows up making amazing trendsetting style choices. I’d hazard a guess that nobody does (I certainly didn’t). Style is a skill that anyone can learn if they take it seriously. Sam Pizzo is one of the best-dressed men in Chicago, and if he admits to a few faux-pas, then we can too. As long as you learn from past mistakes, then people like Sam can help you move forward.