Every well-dressed man in Chicago knows Morris & Sons, a third-generation menswear store where you can expect to be greeted by a family member. People come for that personalized service and sometimes just to unwind with a good Scotch whisky, but they return for the store’s exceptional line-up of menswear collections—a curated mix of big names like Brunello Cucinelli and Stefano Ricci, and smaller brands, including Lardini tailored clothes and Fray shirts.
If you’re lucky, you’ll meet Gary Rosenbaum on your next visit. His grandfather started the business more than 60 years ago, and he travels around the world uncovering the best brands, new and old, for his clients. “We believe strongly in investment dressing,” he says, “and understand the value of assembling a cohesive wardrobe.” Here, he tells Robb Report readers what they should have in their spring wardrobes and how to get the most mileage from these key pieces.

The suit you need now Photo: Courtesy of Morris and Sons
“A standout this season is Lardini’s Mediterranean blue suit. Wear this to the office or a summer wedding, and you are sure to be the best dressed one there! We paired it with a Fray purple and blue check shirt, a Stefano Ricci paisley tie, and John Lobb double-monk strap shoes. Ties are a great way to hit the ‘refresh’ button and give your suit a new look for the season.”

The seasonless jacket Photo: Courtesy of Morris and Sons
“Living in Chicago we always like to keep in mind hybrid pieces for our customers. A perfect example: Baldassari’s laser-cut sweater jacket. It works as a sport coat indoors, or as outerwear for cool spring evenings. Paired with a linen Henley from Eleventy, or a sport shirt from Fray, this navy sweater jacket from Baldassari will be on regular rotation in your closet.”

The all-weather vest Photo: Courtesy of Morris and Sons
“A favorite layering piece is Eleventy’s lightweight nylon gillet made in water-resistant fabric. If anyone knows how to do outerwear cool and effortlessly, it’s these guys. Wear this vest over a T-shirt with your favorite joggers, or try sporting it underneath a suit for that modern day Italian guy look. We suggest wearing your vest with this Brunello Cucinelli sweater—the best knitwear from Solomeo, and pair it with cream-color Cucinelli cotton pants during warmer months, and sophisticated sneakers.”

The go-everywhere sport coat Photo: Courtesy of Morris and Sons
“Kiton’s gray and turquoise windowpane sport coat is a favorite this season. We love the subtle colors and how this jacket can be dressed-up with charcoal slacks or worn casually with gray or white Jacob Cohen denim. A bonus: The half-lined jacket will keep you cool during the warm summer months. We paired it with a cobalt and turquoise stripe Fray shirt to compliment colors in the jacket. Attention to detail is everything: Don’t forget this Drake’s white linen with a turquoise border.”
Rosenbaum’s top 10 wardrobe items for spring:
- Sweater jacket by Maurizio Bladassari
- Blue suit by Lardini
- Checked shirts by Fray
- Necktie by Stefano Ricci
- Lightweight sport coat by Kiton
- Double-monk-strap shoes by John Lobb
- Colorful pocket square by Drake’s
- Outerwear vest by Eleventy
- Blue sweater by Brunello Cucinelli
- Gray denim by Jacob Cohen