Do Clothes Make the Man? Sheri Radel Rosenberg on Whether You Should Suit Yourself

I’m not a woman who loves a man in a suit. It’s not that I don’t appreciate it, but I’ve always been more a (good) jeans and (good) t-shirt kind of gal when it comes to the menfolk.

I grew up in a house where my dad wore a suit every day to work. And I adored how meticulous he was about his look. The beautiful shirts fresh from the dry cleaner. A tie drawer that felt OCD in the best of ways. And the elegance with which he dressed is etched in my mind forever. But alas, I’m a Gen X woman whose idols were not suited men but rock stars. And having always been drawn to creative vs corporate types, the whole suit vibe was lost on me.

The same can be said of my husband, who finds wearing a suit positively squirmy as a creative type in advertising. He and I share a general disdain for dressing up, even though we like clothes. Fortunately for him, he’s never had to “dress up” for work. But we do, on occasion, have to leave the hoodie zone and clean up a bit. And since many of us are going out again, we find ourselves with two fabulous wedding invitations and nothing to wear (he, not me). 

Funny thing about being married for longer than a minute. It takes some time to plant a seed.

For years, I have been telling David to have a suit made. He’s a long drink of water, and his very long torso makes buying off the rack a bit of a challenge for a great fit. To him, having a suit made always felt a bit too dandyish. Too extravagant. And just generally ridiculous. 

During the pandemic, I started following George Hahn, a New York personality and self-described “self-made thousandaire playboy who wears tailored clothing, drinks coffee, and occasionally writes.” I love the cut of his jib, and as an over 50-year-old man, I find his thoughts on style so spot on. He recently wrote a piece on why we should dress up again and, in addition to saying “every man wants to dress like James Bond,” he said:

“Concerning comfort, there’s a myth that nice clothes aren’t comfortable. I’m calling bullshit there. If your suit, jacket, nice pants, or handsome dress shirt are uncomfortable, they’re the wrong size or poorly tailored. My suits are neither too tight nor too loose. They feel like pajamas. Seriously. And a nice, 100% cotton dress shirt (and not the wrinkle-free stupidity) feels like fresh bed sheets. And there’s also a different kind of comfort that isn’t physical. Applying a higher sense of occasion to my life gives me much comfort. Looking nice feels good.”

Wearing a good suit should feel comfortable

That sentiment stuck with me. That is, wearing a good suit should feel comfortable and not something from the husky department you wore at your bar mitzvah. So as we pondered two weddings and what to wear, I started researching suiting and where to purchase something cool. David is not a Brooks Brothers guy. Or a Zegna guy. Or even really a Hugo Boss guy.

On a recent long weekend in the Hamptons, we found ourselves in the Todd Snyder store and loved the staff and the vibe. Todd Snyder, formerly head of design at Polo Ralph Lauren, The Gap, and J.Crew, makes clothes for real guys who want to be stylish but not overwrought. I love his knit polos, beautiful suede jackets, and general understanding of how men want to dress with ageless appeal. Men of all ages can rock a knit polo, a great pair of jeans, or even a suit.

On a rainy Saturday, we went to his new NYC flagship on 26th and Madison (a random location, to be sure, but such a great space) on a mission. There were some excellent off-the-rack options. A navy tux was a particular standout, but not necessary. Small sidebar: the staff at this location are a dream. Every guy is cool but not overly, so to be intimidating, and NICE. So damn nice. Our salesman was a young guy with soft-spoken energy we both loved. As we were browsing suit options, he quietly said to my husband, “You might want to consider having something made.”   

Here’s the thing. David and I are both the same age and turn 52 this year. Much is made of the notion of investment dressing as you age. If you are fortunate enough to be financially stable, investing in yourself for long-term gains can feel great. From a personal trainer to a fabulous facial to a high-quality piece of clothing, thanking yourself for the year of toil and late nights and putting in the “work” is a win. 

So as David thought it over and glanced my way, I nodded yes. Say yes, not to the dress. But to the suit. And just like that, we were in a back room of the store sipping champagne. We were handed over to a rakish British man wearing a fabulously tailored suit that felt more Banksy than banker, and out came books of swatches and fabrics and linings and trims and buttons. Heavenly.

Finding common ground took any stuffiness or hesitation out of suit shopping

It turns out the suit guy was one of us. A young 50-something dude who once DJ’d for a famous band in the New York ’90s. We had so much in common and had such a great chat — from connecting over music, New York in the ’90s, wacky ways to make a living, and how our bodies are adjusting to our age while our minds are not, we were instant mishpocha. Think again if you’re picturing a stodgy sartorial type that was all business. That’s what felt so plussed up about all of it — finding common ground took any stuffiness or hesitation out of suit shopping and made it so relaxed and kicked back.

David chose a dark olive green almost black fabric that is elegant but super modern and unique. The tailor was the type of guy who had been fitting men’s suits forever and was beyond a pro. I so enjoyed watching my husband treat himself to something so decadent and unpretentious. As you would imagine, custom suits can range from Oh, my Lord to Oh, ok when it comes to a price point. Fabric plays a role, of course, and brands like Suit Supply (a fav of George Hahn’s) offer custom options well under $1K.

He also got a fabulous off-the-rack suit that is the perfect antidote for men who are suit averse. This black seersucker “travel” suit (the fabric alone is excellent) is softly tailored to be worn more casually, and the pants have a drawstring for comfort and would look just as fantastic with a good loafer as they would a Chuck Taylor. Plus, the jacket and pants can be worn as separates.

Has this experience changed my take on men in suits? Absolutely.  And even if your idea of dressing up is wearing jeans without holes, think about investing in something you’ll have for a long time. And because there’s nothing I like more on myself than menswear-inspired looks, I may have to get one made, too. I wouldn’t say I like formal dressing beyond compare.  But maybe if I had a custom tux, I’d feel more up for it all? Growing up and dressing up in something custom has its benefits. Because as my grandmother once said, “good is good.”

For more information on Todd Snyder Made to Measure, click here.