The Unfortunate Fear of Being “Too Dressy”

A friend invited me to be his plus-one for a concert of Brahms at Carnegie Hall this past weekend, with a supper in a fancy restaurant immediately following. Though I certainly appreciate classical music and often listen to it while working, the classical music scene is not my world at all. I basically feel like Tom Ripley in these situations. The music, however, is always gorgeous, and my friend is smart, funny and fantastic company.

The combination of classical music and Carnegie Hall says suit and tie to me (and my friend, thankfully). As I looked around the audience before the performance started and at intermission, it was obvious that the combination of fine musical art and an iconic Manhattan venue inspires something quite different in other people’s sartorial inclinations. Of all the men in attendance that evening, I’d say about 40% were in a suit or jacket, with even less wearing a tie. For a classical music performance. At Carnegie Hall.

The seismic shift away from dressing up for any occasion depresses me. At weddings, funerals, Broadway shows, nice restaurants and even the Metropolitan Opera House, fewer and fewer men find it necessary to wear a suit or jacket, let alone a tie. And if it’s black tie or black tie optional? Don’t get me started. It’s all about the unironed casual shirt (which is apparently the new dress shirt), the sweater, the jeans or even the hoodie, and sometimes sneakers. Nowadays, personal comfort trumps all else in the relentless pursuit to have the super-cozy, fleecy, snuggy-on-the-sofa-at-home feeling wherever we go, no matter what it looks like. And athleisure dressing like one is living in a perpetual yoga class is almost worse.

Don’t get me wrong: I love being comfortable. Sitting on the sofa at home in a t-shirt and sweats with a nice blanket and a new season of House of Cards in front of me is one of my favorite ways to be. The only time I’ve ever been more comfortable was in my mother’s womb, but, as an adult, I don’t feel the urge to reproduce that experience with clothes. That’s what sleeping in my bed is for. At some point, you’d think one might be interested in growing up, particularly when stepping out of one’s home. Instead, we’re at a soft, frumpy, dumpy time in our culture where many grown men go about their day dressed like they’re on their way to baseball practice after school.

Though they’re not necessarily as comfortable as a hoodie and basketball shorts, my suits are tailored to be very comfortable. I often wear them all day, and then into the evening, quite comfortably. But the way men avoid wearing suits and jackets at all cost these days, you’d think jackets were lined with thumb tacks. It’s as if anything that doesn’t entail denim and sneakers is a fancy foreign language.

I can only speculate why so many men have moved away from “dressy” clothes. Maybe it’s a rebellion/anti-establishment thing. (Though wearing a suit these days feels more like the rebellious move.) Maybe it’s a Silicon Valley thing. (Ever seen a picture of the “Fairchild Eight,” the guys who founded Silicon Valley?) Maybe it’s an “I don’t want to be my father” or “I don’t want to look like my grandfather” thing. (But doesn’t gramps look kinda cool in those old pictures?) Maybe it’s an “I don’t want to dress outside my station in life” thing. (It worked wonders for Tom Ripley and certainly opened doors for me.) As I said, I can only speculate. What I do know is that all men – regardless of age, height, size, shape, whatever – look their best in a nice tailored suit. Find me any man who doesn’t look at James Bond, Cary Grant, Steve McQueen, Frank Sinatra or vintage Michael Caine and say “I’d love to be that.” For some reason, a lot of men seem to be afraid of it.

What are the occasions that get men to actually dress up beyond a sweater anymore? What are men saving the suit or jacket for? It’s like the sartorial equivalent of covering the nice living room furniture in plastic, saving it for that truly super special occasion that never comes. What is that occasion?? Invitation to the White House? The Queen’s funeral?

This isn’t exclusively a phenomenon among younger generations, either. The other night at Carnegie Hall, I saw many older men who clearly weren’t interested in looking good for their wives anymore. It’s as if they’ve told themselves “Well, we’re here, bound together for life. What’s the point anymore? Let’s let it all go. Fuck it.” Thrilling. If that’s what marriages or long-term relationships look like, I’ll pass.

And this isn’t about money, either. I have less money than almost anyone I know. It’s about making do with the best you can afford and giving a damn.

It’s no news to anyone who knows me or reads this blog that I often wear suits, even though there’s nothing about my professional life that technically requires it. It’s a choice that makes me look nice and feel good. Whenever I step out for the evening for theatre, fine performing arts or a nice dinner in a suit or jacket (or anything that isn’t denim or a sneaker, basically), I invariably get: “Wow, you’re so dressed up.” That’s a bummer. And when people follow up with “I feel so underdressed,” I feel badly for them. Between being overdressed and underdressed, I’ll take the former any day.

So sport a suit or jacket and a nice pair of shoes. Jazz it up however you wish with a fabulous tie, a crisp shirt with a terrific pattern, interesting pocket linen or those funny socks if you like. Give life a renewed sense of occasion, dress up and enjoy. It won’t hurt you. In fact, you might even get some nice compliments, get a meeting with a new client or get a better table. Hell, you might even get laid.



  1. In my experience and from what others have told me, it’s actually women who share much of the blame for the situation you describe. They discourage their husbands and boyfriends from dressing more nice because they don’t want them to be noticed by other women.

    • notiwthstanding the dangerous sexism of such an overgeneralization, that hardly explains the sloppiness of the single men who are ostensibly trying to snag one of those possessive and controlling women

  2. I tend to disagree with Charles. Being in the menswear industry for most of my career, I have heard countless women shopping with their boyfriends/husbands picking out a suit, tie or nice dress shirt and saying to the man “you would look so nice in this”, and yet almost every time the man will brush off the comments and move on to something more casual.

    Note to all men out there..if your lady says she would like you in something, buy it (and wear it).
    As one wise women once said “A suit is to a woman what lingerie is to a man.”

  3. Thank you so much for this post–a pleasure to read, and very kindly stated. How many times, in my years near D.C., had I driven past Mount Vernon Park on the Potomac on a crisp, stunning fall day and seen people out walking…in sweats? I used to dream of seeing tweed. When I moved to New York, I was pleased to see much better dressing overall–and just as you say, not about spending a lot of money but about making an effort–but this disappears at the theater or at the Met. Is it tourists? Tourism in America became equated, sometime back, with the wearing of fanny packs, sneakers, and jeans for many people. Like a travel uniform. As you say, it’s about sense of occasion, sprucing up, which I really believe makes people feel better and more festive–if not the wearer, surely for the viewer. Thanks for the encouragement!

  4. DJ (The original) Reply

    This sounds like one of my rants! I cannot stand the “I can’t be bothered to put on clean clothes, much less something proper for your formal evening wedding, funeral, sit-down dinner, etc.” We spent 20+ years shooting weddings and saw the unfortunate demise of dressing for church and weddings go from suit and tie for men, nice dress or pant suit for women, to sloppy, dirty, casual clothes you’d wear to mow your lawn. And if I hear one more parent say, “It’s not worth the argument to get little Johnny to put on clean clothes,” I’m going to scream. Who’s running the show? Little Johnny, obviously. And he’s not going to learn how to dress properly if mom and dad don’t teach him, even more so if mom and dad look like they just got up from a nap themselves.

    My friend, a male teacher who knows how to dress, talks to his high school students about proper dressing for proper occasions. He even asks the students why they think that “back in the day”, when men and women wore suits even to the grocery store, there was less crime. He asks them how they feel when they clean up and put on a suit or nice dress. They all say they feel better and have more confidence. Lesson learned (we hope).

    I love dressing up! And have been accused of looking “dressy” because I’m not the type to go out in sloppy T-shirts or sweatshirts. My husband looks awesome in suits, and always wore them to shoot weddings, even if the guests wore T-shirts. He was a professional and dressed like a professional. And guess what? People treated him like a professional. The last formal evening wedding we attended, the photographer wore jeans and a T-shirt. My husband was appalled!

    One of the reasons I love watching old shows like “Andy Griffith” is to see how the people dressed. They wore suits to see a movie! People used to care about their appearance and I truly think it made a difference in how society acted.

    Although I think the trend in “athleisure” has less to do with athletics, leisure or even self-esteem and more to do with the fact that we’ve supersized our butts out of our jeans. I admit to being not in the best shape, thanks to a long-term illness. But a cute dress covers my figure problems better than a sloppy T-shirt. And makes me feel better!

    BTW~ Married 26 years and we still dress up for each other! A healthy relationship acknowledges that you can’t look like a cover guy/girl 24/7 and you accept each other in comfy mode, but you also care enough to want to be attractive to your spouse and do so when need be.

  5. DJ (The original) Reply

    I’d like to point out that I made it through my entire rant without saying our bad dressing is tearing apart the fabric of our society! 🙂

  6. In part, it may be tourists, however I don’t think that can account for the large percentages. (After being mugged traveling once, my partner and I consequently traveled with pretty basic clothes, until we arrived in Rome with nothing better than t-shirts. OMG, Rome, where the men are _gorgously_ dressed. I felt embarrassed to walk down the street! 🙂

    Anyway, I think it’s marketing. Decades and decades of name-brand clothing bombarding people with messages of “this is how you should look”. There is scant little marketing saying, “hey men, a suit is what you need”, and certainly nothing from high-profile branding agencies staffed by smart, highly paid psychologists who know how to manipulate you. If Adidas start making a three piece suit (with three stripes down the side, naturally) expect to see them around in abundance.

    “Brand loyalty” is something that drives me totally crazy. The inane stupidity of being an unpaid billboard on the street is yet ubiquitous! And have you ever seen an “Ugg Boot” ad? The most ugly part of the ad is always the boot, yet people see this and wear them… *out in public*!!! (They were only ever an inside clothing article in Australia, like a nightgown). Look at this for comedy – http://thumbnail.image.rakuten.co.jp/@0_mall/roupas-m-m/cabinet/ugg/bailey-thum.jpg Srsly!? (Ladies, just don’t wear Ugg Boots out. Never, ever. I can’t think of anything more grotesque.)

    Add to this, cheap suits and awful shirts that many men wear. Certainly not inspiring. This is what I used to rebel against when my well-meaning mum took me shopping. (Had I grown up with my dad…???) I take comfort in that, as far as I can tell, suits and fine dressing are making a comeback, in part, through smarter marketing, customer service, and yes, brand-loyalty.

    • Sorry, ‘cheap suits’ was bad word choice, as good folks like yourself and Mr Gunn have shown us, there are plenty of fine, cheap suits! (More that men often don’t know how to choose the _right_ suit, or when or how to get effective tailoring done.)

  7. While the specifics of this article pertain to clothes in the literal sense, the ethos of it transcends that limitation and pertains to our attitude towards all aspects of our work and our selves. Why not strive to be “over – dressed” (as in, over kind? over generous? over thoughtful? over prepared?)

  8. Great article! Thanks! I always subscribe to the thought, expressed by someone whom I can’t remember: “There’s so such thing as being overdressed. It always makes them wonder what cooler event you might be attending later.” 😉

  9. Great post.

    I did not read the comments above and they may have touched on this point, but I do love the fact that those with little money or no experience in dressing well can attend events and venues and not feel “less” or stand out in a humiliating way. But, I do wish there were more men like yourself showing men they do not have to be wealthy to dress well and look like they care. I am afraid a generation of men will never understand what it feels like to dress like a man and the sense of confidence that comes with it. The research proves and the reality shows about “makeovers” back it up … you feel better about yourself, feel more confident and in many ways, improve your life when you dress well. Please keep up the good work.

    But, for now the silver lining is, the scarcity of well-dressed men makes us stand out all the more …

  10. This is so dead-on! My sentiments exactly. It seems that the era of “dressing up” is gone…atleast for now, it is. Don’t you have to “hit bottom” before bounding back? I can’t imagine fashion getting any more rock-bottom awful (or non-existent) than it is now. The thing is, those of us who refuse to fall into this primordial ooze of badness have to continue to dress…if only to show the rest of the world that a suit-and-tie is not passé, or dated…or “old fashioned”. You’re so right that Cary Grant, Sinatra and the others you named are considered by most adult men to be the icons of “how it was done”. Were they so intimidating that it’s not even worth TRYING to emulate their statements of personal style? And agreed: It does not have to be a “money thing”. Between eBay and upscale thrift stores, a guy can look like a million for pennies per serving. To me, it all boils down to laziness. It’s so good to hear someone else say that they refuse to fall into this societal morass of mediocrity. My motto is: “Life is short…you’d better dress up!” (And on a tangential note, how disgusting is it that the Campbell Apartment in Grand Central Station is getting kicked out, to be replaced by a “dress-code-free” douchebar? The new managers are actually BRAGGING about how they’re eliminating the current dress-code! What a disgrace!).

  11. I’m late to the party but just had to comment! It was so refreshing to read this. As a woman who is mostly in dresses and skirts, particularly with a vintage flair, I have the same issue. Living in southern California, I am surrounded by athleisure, stripperwear, and general frumpiness… But I love my sense of style and would feel uncomfortable trying to “blend in”. I have always felt that dressing nicely is a form of respect- for myself, as well as the occasion, setting, and other people present.

  12. Forrest L Howe Reply

    I have read this post many times. I don’t tire of it at all! Maybe it’s my insecurities, but the only time I feel better than when wearing a nice tailor is suit is when I wear black tie.

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