The Kentucky Derby is one of the biggest sports moments of the year. And while we love the performance of the horses and the mint juleps, I have a soft spot for the outfits. I got my start in the menswear world by selling suits. And while most of my clients were there for the suits for their weddings or that of their friends, every year, I got inundated with guys looking to peacock for the Kentucky Derby. It is the one time a year that guys are ready to really let their personalities shine. But I always wondered why men never wanted to stand out until an annual occasion prompted them to. So, I reached out to my friend, Jordan, who is the best-dressed guy at Paul Fredrick, to talk through how we, as men, can dress like it is the derby every day. And, as expected, he didn’t disappoint.
Most men are not walking around looking for a fashion moment in their everyday lives, but at the Derby, it is part of the tradition. It gives guys permission to have a little more fun with how they dress, wear more color, try more pattern, and show a more personality than they normally would. – Jordan Hauser, CMO (Chief Marketing Officer) of Paul Fredrick
How do I start dressing to stand out?
When I sold suits to men, the biggest hurdle was getting them to buy in. How do I get them started? I got the same questions all the time. How do I get started? Wouldn’t I be overdressed? Wouldn’t people think that I was trying too hard? While some of these questions made sense, at the end of the day, I just had to convince them that what other people thought of them was inconsequential. Men needed to dress the way they wanted, whatever made them happy. So, I asked Jordan how to get started. How does a well-dressed New Yorker who has to sell this to men on the daily basis convince men to get started? Here is what he had to say.
“Start with one statement piece, whether that’s a suit or a blazer, and build around it. You don’t need every piece to compete. The guys who look the best usually have one or two standout elements, and the rest of the outfit accentuates them. Fit matters most. If you are wearing something bold, it needs to be tailored and put together. And I would say lean into the occasion, have fun! The Derby is the day for a man to have his fashion moment. Also, it can be hot, so lightweight fabrics like seersucker, linen, and chambray are your friends. And wear comfortable shoes! Even if you look good, if you’re miserable, it’s not going to be fun.”
What should be my go-to on Derby Day?
Look, I am a huge fan of the Derby. As a men’s style consultant, I wanted nothing more than for my family, friends, and clients to let their flags fly. Have fun. Stand out. Be the beacon of fun that I knew they were on the inside. The Derby is the moment every year when I see my friends do that. I will go on their Instagram and see them wear those things they would never dare to rock daily. So, I started to think about those guys who didn’t usually go to the Derby but are making 2026 the time. What should they pick up? What would a guy like Jordan, who, when I met, was wearing an enviable red pinstripe linen suit, reach for when he dressed for the Derby?
“Seersucker is the Derby classic. A blazer with white pants works, or you can go for the full seersucker suit if you are ready to commit. It also comes in more colors than people realize, so you do not have to stay in the standard blue and white. Accessories pull the outfit together. A tie is optional, but a white cotton pocket square should be required. Add a braided belt and loafers, and the outfit feels finished without trying too hard. If seersucker feels like too much, go with a cotton or linen khaki suit. It is timeless, and sometimes the best Derby outfit is the one you actually feel confident wearing. People can tell.”
Do I have to wait for the Derby every year to peacock?
Here it is, gents. This man, who dresses better than all of us, is about to tell you what I have been saying since I first started in this industry: The Derby is the Super Bowl, but there is a whole season of dressing before it. And after it. If you like the way you look when you dress up for Derby day, there is no reason you should have to wait for 2,000-pound animals to run circles in Kentucky for you to dress up and have fun with your look. Instead, put all of this into your daily ensembles and have fun with life. You like something? Wear it.
“Whenever I’m building a dressed-up look, I’m always thinking about how the pieces can work beyond that one moment. A great dress shirt, pocket square, braided belt, and loafer combo all translate into everyday life. You may not wear the full Derby look to dinner, but if you bought a statement suit for the Derby, wear the jacket with more casual pants. That is how you make the purchase feel more versatile and less tied to one occasion. And fit matters. Get your suits and blazers tailored. A bold jacket is a lot easier to pull off when it actually fits.”
How can Paul Fredrick help my day-to-day Derby peacock?
Paul Fredrick will always be one of my favorite dress shirts on the market. So they have you set in that department. But Jordan was a guy who was so put together when I met him that I knew there was more to it than that. He was wearing a linen suit but didn’t even have a dress shirt on!! So I asked how Paul Fredrick could help me and the other men in my life dress to stand out every day, and he didn’t disappoint.
“We have an amazing assortment of suits and blazers in seersucker and linen. The base of the look is always the dress shirt, and we make some of the best non-iron dress shirts in cotton and linen for those hotter moments. My favorites are the white linen suit with the red stripe, and if you’re feeling fun, try the red striped double-breasted linen suit. Everything is built to mix and match, so if you already have a solid pair of pants you like, just buy the suit coat and build from there.”
