To anyone who knew Clifton Wilson in high school, it comes as no surprise that he found a career in fashion. He was voted best-dressed by his senior class after all. After years of working in retail and styling at Nordstrom, Clifton had a good idea of what his customers liked to wear. At this time, he also noticed that men’s accessories lacked that one piece a guy could wear to show off his personality. In 2009, Clifton teamed up with Ontario Armstrong to start Armstrong & Wilson, a Philadelphia-based accessories brand offering pocket squares in fresh designs and bold colors. Using the tagline “It’s okay to be a square,” Armstrong & Wilson has revitalized men’s fashion with a modern sensibility and attitude that has been noticed by the likes of LeBron James, Mos Def, Carson Daly, and The Roots just to name a few.
We had the pleasure to talk with Clifton and ask him about the philosophy and inspiration behind his brand, his advice for grooms facing the “boutonniere or pocket square” question, and the celebrity he would love to see wearing Armstrong & Wilson.
When did you know that you wanted to be a designer?
I knew when I was around 18. I was going to go away to college to run track. But right after graduation, I found out that I was going to be a father. With my plans to run track on hold, I started thinking about my other passions – sketching and dressing, or fashion. With fatherhood came the need for stability. So I looked at the Art Institute of Philadelphia and went there for fashion design.
How did you get your start in men’s accessories?
My first job in high school was at Smalls Formalwear, a tuxedo shop in Philadelphia. Every year just before prom, the store would host a fashion show at my high school to show students their latest tuxedos. I was in the show, became friends with the event coordinator, and he gave me a job. I worked at Smalls for about seven years doing weddings and special occasions. So my fashion background starts in tuxedos and men’s formal wear.
What is the philosophy behind Armstrong & Wilson? How is your approach to designing accessories different from the rest of the industry?
When we design our collections, our goal is to be unique and not follow what everyone else is doing. When Ontario and I established our brand, we knew that we wanted to start out with pocket squares. But we had to be different, because at the end of the day, it’s just a pocket square that has been around for hundreds of years. Our design needed to be more than just a square piece of fabric.
Pocket squares are traditionally silk. We started playing around with different textures of fabrics, looking at wool, cashmere, cotton, and linen. And then we introduced the Armstrong & Wilson signature button, which distinguished us from the rest.
Yes, I immediately noticed the button detail. It’s subtle, yet makes a statement. How did it come about?
Ontario and I met at school, became good friends, and started talking about doing a line of accessories. By this time, we both had been selected by Esquire as best-dressed men in Philadelphia. The magazine invited us to a party in NYC. It was the perfect chance to introduce our first designs, which were made of the same cotton fabric used for dress shirts. We sat down and were like “How can we take this pocket square to the next level?” And that’s when I had the idea to add a button, similar to the button on a dress shirt. And the button feature was functional – it let you open and close the square and fold it any way. We showed the pocket square to some people at Esquire and they liked it. That’s when the idea for Armstrong & Wilson really took off.
Your fabrics not only look incredible, but are also high quality. What goes into selecting the different patterns, colors, and materials used in the Armstrong & Wilson collection?
Ontario and I both worked at Nordstrom. For about 8 years, I worked in men’s suits there. My work styling men’s formal wear goes all the way back to my days at Smalls. When we design our pocket square, we are always thinking about that guy we were helping to buy clothes. What style and colors is he going to wear?
For instance, neckties started to get a little jazzier with vibrant colors and patterns. A busy pocket square isn’t going to compliment a busy necktie. So we are going to offer a collection of just solid pastel shades. There is always going to be a pocket square to match no matter how busy the tie is. At the same time, we are thinking about the more conservative guy wearing a solid necktie who wants to make a statement with his pocket square. He’ll find designs with bolder patterns and colors. For us, the pocket square is a way to express personality and style.
Do grooms come to Armstrong & Wilson looking for wedding accessories?
We’ve been fortunate enough to do a few high-profile weddings. One of our biggest wedding parties was for NBA basketball player Amar’e Stoudemire. We did a custom pocket square for his groomsmen.
The great thing about our pocket square is that it comes in a specially designed box with our slogan “It’s okay to be a square.” We wanted the packaging to make an impression. As we started doing more and more weddings, grooms were giving the pocket square to their groomsmen as gifts. It’s the perfect gesture of appreciation because your friends are presented with this really nice box that has a sliding drawer. Inside is this stylish pocket square, which can also be monogrammed. And since a lot of men rent their tuxedos, the pocket square is the one thing they can keep and remember the day when they stood by their best buddy.
Boutonnieres have always been worn to add a bit of flourish to a man’s suit and complement bridal attire. Have you noticed a trend of men opting to wear a pocket square instead of the traditional boutonniere?
It used to be one or the other. If you were going to wear a pocket square, you weren’t going to wear a boutonniere and vice versa. One thing you want to avoid is making the groomsmen’s jacket too busy. Complement the suit, but maintain elegance. With our wedding pocket squares, it was about merging the two looks together – that’s why we added a little rose button.
Weddings are so different now – some guys don’t want to wear jackets. I will say this though, you should always wear a vest even if the wedding falls in the middle of summer. Because you can take your jacket off and still look put together. We’ve all seen that guy in a sweaty, ill-fitting dress shirt. A vest keeps everything looking sharp and where it should be. I’ve seen both formal and casual trends in men’s wedding attire. You can dress a suit up with a pocket square and boutonniere, or go for a more casual look by taking off the jacket and attaching the boutonniere to the vest.
So you think a man can pull off wearing both a pocket square and boutonniere?
Yes, I actually wear them together. It comes with the job, but I am a big stickler about accessories. For me, it’s all about finding that balance of not overdoing it, but doing it enough while making a tasteful statement. It depends on the size of the boutonniere and how you are actually wearing the pocket square. For weddings, I like a clean and classic look with the boutonniere. Don’t wear a puffy pocket square – it’s going to be too much. Rather, wear the pocket square with a simple, straight across fold, showing a quarter inch fabric with the rose button and a boutonniere. I feel that every tuxedo, suit jacket, and blazer should have a pocket square because it shows you are paying attention to detail.
What advice do you have for the groom getting ready to choose a pocket square for his wedding?
If you are a clean-cut guy, do a classic white pocket square. If your style is a little bit funkier, choose a pocket square that is an extension of your personality. Brighten it up with colors or a pattern. Of course, you must consider what the bridal party is wearing.
What do you do for creative inspiration?
I’ve never been a designer that sees inspiration in things like architecture. My approach comes from direct observation and experience. I stood on the floor at Nordstrom for years dressing men. I always go back to that and put myself in the customer’s shoes, so to speak.
And many of my customers were women gift-shopping for their husbands. When they saw an accessory in a sleek-looking box, their eyes lit up as if saying “Oh yes, this is beautiful.” From the beginning, attractive packaging was very important. When we design, we are thinking about the entire product from the thread stitch to the finish of the box it comes in. Our pocket square is incredibly stylish on its own, but seeing it displayed in a great looking box adds that extra touch of class and sophistication.
It sounds like your time working in retail and styling has greatly influenced your sensibility as a designer.
Definitely, I know every holiday season Nordstrom will be selling a camel-colored sport coat. Our question is then, “What goes with camel?” The answer is brown or tan. So we’ll design a collection with a seasonal fabric like camel cashmere and accent it with brown piping and a leather button. Without question, this pocket square will have a place in a man’s wardrobe during the holidays.
Our inspiration also comes from people watching. We don’t stray from what we know and see men actually wearing. As men, we are very visual and want our accessories to coordinate with our whole look. And if we get a compliment on a pocket square, you better believe we’ll be making it work with other outfits.
Does Armstrong & Wilson have any style icons, past or present?
Looking back, the Rat Pack and Cary Grant had exceptional style. When you look at classic Hollywood movies and pictures, men wore suits to cut the grass and hang out on the corner to play checkers. It was just a totally different era when men took more pride in what they wore and how they looked. A man of good style today is David Beckham. UFC fighter Conor McGregor always looks super polished. It’s about confidence too. A stylist can put you in a fantastic suit, but if you don’t have the confidence to back it up, the look just falls apart.
Some of the most stylish athletes, celebrities, and influencers have all worn your designs. Is there anyone in particular who you would love to see wearing an Armstrong & Wilson pocket square?
We were fortunate to get some really cool people to wear our collection early on. It was a huge moment for us when LeBron James stepped out in one of our pocket squares. He has free access to every major designer, but decided to wear Armstrong & Wilson.
Again, I would love to see David Beckham in an Armstrong & Wilson pocket square. He’s about as close to a style icon as we have today and could take the pocket square from black tie to a more casual look effortlessly.
What’s on the horizon for Armstrong & Wilson?
Right now, we are in about 50 Nordstrom stores and recently collaborated with Chris Bosh of the Miami Heat on a collection called Mr. Nice Tie. We have another collaborative project with an NBA player underway. I can’t talk about it too much, but we are very excited.
The primary focus is establishing Armstrong & Wilson as a leading designer label in men’s accessories with plans to introduce socks and lapel pins. Looking far ahead, we want to get into men’s suits, because that is where it all began for Ontario and me. In the meantime, we are going to keep working hard on new and stylish accessories to complement the future menswear collection by Armstrong & Wilson.