The Lost Art of Dressing Appropriately

Not too long ago, one of our longtime contributors (The Salty One) forwarded a link to an insightful and timely article by well-known columnist George F. Will.

You can read it HERE.

Mr. Will makes a few good points. He bemoans the creeping 24/7 casual nature of dress today. He notes the reverse-snobbery of a tech billionaire who conducts business in T-shirt, jeans, and sneakers. Perhaps most importantly, he points out that not all occasions are created equal: dressing up is a sign of respect, for others and for the event, ritual, or venue.

I’d like to add that I’ve met more than a few ‘always ever-so-casual’ people. What I’ve realized is that many times it’s not that they don’t want to dress well; often, they don’t know how to dress well.

Like all of us, they’re bombarded with advertising and influencers, the latest trends and must-have accessories, logos and brand hyper-awareness. They become like a deer in the headlights: paralyzed with indecision, unable to move, or in this case, choose. Not wanting to look foolish, not knowing who to listen to or dress like, in the end, they decide to not make an effort as a safe fallback position.

In fairness, the result is not always terrible. Some people (especially Parisians) opt to wear black as a default wardrobe choice. It’s simple, economical, and, for better or worse, does not communicate anything about the wearer. Wearing all black all the time can be tedious to friends and family if accompanied by a cynical, seen-it-all attitude, and certainly uncomfortable during the summer…and perhaps at weddings.

Most of the time, however, neglecting one’s wardrobe out of fear, disinterest, or ignorance is not helpful. And I say ‘not helpful’ because I’m first and foremost a pragmatic person. Choices must, in the final analysis, work on a daily basis. Clothing choices are best when they are functional, comfortable, versatile, and economical. The ‘message’ they communicate to others is equally important, as we are judged by others often by our appearance, and clothing is a large part of that.

We discuss this topic often here, but it’s worth repeating: dressing appropriately is key. It sends a nonverbal but potent message to others about you and how you feel about yourself. It also sends an often subconscious message to you, about you, and how you’re going to behave and perform on a given day.

Teachers will tell you that students behave better when dressed for ‘photo day’ or more formal school events. Productivity is increased, even when working at home, when workers dress professionally. Clothing works ‘from the outside in’, making us a creature of our uniform, as Napoleon once said. Our identity and self image is polished, if not sculpted, by our daily choice of garments.

I’m going to refrain from putting a label on the optimum way to dress. ‘Preppy’ as been corrupted in recent years and ‘Old Money Style’ is my favorite, but might be a little ‘old fogey’ for someone in their 20s. (Fear not, you’ll come around.)

So I’ll simply leave you with a request.

Make an effort. Give it some thought. Show some respect, for yourself and others.

Dress appropriately.

  • BGT



12 thoughts on “The Lost Art of Dressing Appropriately

  1. Just home from playing pickleball, and reading this. A dud story, but it’s top of mind: One of the women wore a t-shirt that had the message on it: I REALLY DON’T CARE. DO U? Some of us will recall Melania Trump wearing a jacket with this message on it several years ago. The wearer of the t-shirt needlessly reminded all of us where the message first appeared, and it irritated a lot of us. It took some of the enjoyment of the day away. More in the spirit of what Byron wrote, I’ll say this: yes, I’ve found dressing appropriately matters. Being better dressed lifts my mood. Seeing others well dressed lifts my mood. About twenty years ago, I saw an exquisitely dressed older woman at the grocery store: pastel green suit, matching shoes. I approached her and told her she looked terrific. She let out a big sigh, and thanked me, saying how much work it took her these days to put all of it together. She was thrilled that her effort was noticed. Obviously, it made an impression as I still recall it all these years later. (Thanks for letting me vent!)

  2. I pi ked up a friend Wed. to go to church. She was wearing lounge pants made of tshirt material. I was appalled but didn’t say anything. She justified her attire saying it was too cold for a skirt. It was cold but why does it need to be warm to dress nice? I noticed other women in jeans. People use the excuse that it is not Sunday so it’s ok to dress down. It is not ok.

  3. I picked up a friend Wed. to go to church. She was wearing lounge pants made of tshirt material. I was appalled but didn’t say anything. She justified her attire saying it was too cold for a skirt. It was cold but why does it need to be warm to dress nice? I noticed other women in jeans. People use the excuse that it is not Sunday so it’s ok to dress down. It is not ok.

  4. Preppy sometimes does look like an Anime movie vomited on the wearer. Just break out your ivy league dressing guide books and put the preppy style back on track.

  5. I read two different pieces of advice on how to dress early in my professional life that I believe came from two different advice-givers, and I wish I could recall the sources because they have both stuck with me and are principles I have tried to maintain (and pass along to my kids):

    1) Dress on the bell curve for your surroundings. Not necessarily dead-center if that does not appeal, but not an extreme outlier on the formal-casual spectrum, or the all black to bright colors spectrum, etc. In one of my prior jobs, the men generally wore slacks and button-down shirts, with roughly 2/3 also wearing ties. Suits and sportcoats raised the curiosity of what higher-ups were being met with and why; conversely, the younger men who showed up in cargo pants and wore polar fleece vests over their shirts were considered odd and potentially unreliable. While there was more variety in what the women wore, similar outliers would receive similar response – raised eyebrow and murmurs of “interview?” for a suit, a bit more watching-carefully-for-mistakes for clothes that seemed a little too dressed-down.

    2) Whatever the (formally codified or known-by-osmosis) dress code of your organization, your clothes should be the best attainable-by-you quality of that type. If you’re in a tech company where jeans and “funny slogan” t-shirts are the norm, let the jeans be in impeccable condition and the t-shirts be sturdy and organic. If khakis with polos or button-downs are the norm, high-quality khakis and polos will garner more respect than low-quality suits.

  6. I’ve come to the conclusion that clothing works from the outside in and the inside out. Clothing affects how you feel about yourself and therefore how you act. But it also affects how others perceive you and therefore how they treat you, which affects how you feel and act which affects how they perceive you. It’s a self-reinforcing cycle. Also, (Warning: Word Police) one neglects one’s wardrobe out of uninterest, not disinterest.

  7. If I stop and take a conscious moment to think back, by always dressing appropriately for an occasion, plus that little bit extra, I have always been treated differently to most others. That is more courteously, given more leniency in situations, bumped up to business class more often and too many other occasions to list. Is it just my clothing ? Probably not. But it was a good place to start and something I have direct control over. I can probably thank my parents for insisting on that.

  8. Michelle Matland, the costume designer for Succession, discussed in a recent New York Times profile how she dresses from the bottom up

    “Where do you start?
    Always the shoes. Start at the bottom and grow the character from there. Shoes are the most important article of clothing on a person’s body. They tell you everything. It’s like if you’ve ever fallen in love with a guy and you then see the shoes and realize, Oh, this is not going to work.”

  9. We just returned from a trip to Italy and brought our young teenagers along; it was their first trip abroad. I communicated to them early on that we would not be wandering around in shorts, tank tops, and flip flops. We have always been a family that does our best to dress for the occasion because it’s a sign of respect to the people who are hosting you, be that a dinner party at a friend’s, the symphony, even a school musical. I tell my kids when you visit someone’s home you respect their rules and follow their lead. This goes for visiting other cities/countries as well. We are coastal people who moved inland and have lived in a landlocked state for 11 years. The one thing I continue to instill in our children by both words and example is we dress up for special occasions/nights out. I don’t care if all the other parents are shuffling around in their gym shorts and cross trainers. If my child is receiving an award, I’ll be wearing at my most casual a darkwash pair of jeans, attractive flats, and a nice top. Sometimes black slim fit slacks, or if it’s the right event/warm enough, a day-to-night kind of dress. Have respect for others by having respect for yourself.

    We saw a few Americans who leaned hard into the stereotype. They paid for it with having to wrap plastic around their shorts or be refused entry to places such as the Pantheon and the Vatican. At dinner one evening a group came in, ordered French fries for their children (it wasn’t on the menu), and when they got up to leave I was appalled to see one child (about 9-10 years old) wasn’t wearing any pants. As in, only a t-shirt. I honestly couldn’t believe it. I thought the ugly American trope was an exaggeration until I saw that. Absolutely embarrassing.

  10. I went to a Broadway show a few months back. Most of the people there were dressed horribly. Pajama pants, hoodies, torn clothing. It was appalling.

    (The children had atrocious manners and their parents were even more rude, but that’s another rant.)

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