Why I’m Still Wearing Tailored Clothes Going Into 2022

Three years ago, I defended why tailored clothes are still exciting in the context of the popularity of streetwear and hype sneakers, which ruled the forefront of mainstream menswear at the time. Of course my interest in menswear had taken hold about 10 years prior to that, when suits with narrow lapels, tie bars and Mad Men were at the forefront of peoples’ minds. From there, the #menswear movement on Tumblr put Neapolitan details like soft shouldered-jackets, open patch pockets, and soft construction on the map. 

But as with any trend, those things waned in popularity, and streetwear took over. It was a bewildering time for folks with more classic sensibilities, but in the three years since that original post, tailoring was beginning to make somewhat of a comeback. Designers like Aime Leon Dore began creating looks mixing streetwear aesthetics with tailored pieces, even doing a collaboration collection with Drake’s. We weren’t back to the heyday of Tumblr in 2012, but at least tailoring was part of the conversation again.

And then, 2020. I came across that post just a couple weeks ago, and it was interesting to read given everything that’s happened in the last two or so years. Today the continued relevance of tailoring is in doubt once again, but instead of another fashion trend threatening it, it’s a complete re-orientation of peoples’ attitudes about dressing in response to lockdowns and other pandemic-related lifestyle changes. Previous threats to tailored clothing were the gradual casualization of society; this feels more existential. 

But I’m still trucking along in Italian tailoring, leather-bottom shoes, awesome long coats, scarves and even the occasional tie. And I’m still excited enough about all that to be writing about it online. Why? 

Let’s revisit those points from 2018 of why tailoring is still relevant, and update them given the context of the pandemic.

1. The pandemic has proven that much of what we take for granted is less stable than we thought, so why not wear the good stuff as often as you can? A friend of mine from work was recounting to me the other day how difficult it was for her to navigate a stage 4 cancer diagnosis 20 years ago when she was in her mid-30s with two small kids at home. She beat that cancer, despite many obstacles, and since then has lived a life of gusto. She doesn’t accept the status quo in her approach to her work; and she pushes herself and her family to experience life to its fullest, to make amazing memories, and truly live life to its fullest. In light of that kind of life/death perspective, of course it’s somewhat silly to even care what clothes you wear. But then again, how we dress ourselves can express who we are, and can be a creative outlet as well. All kinds of things seem trivial in comparison with the starkness of death, yet it’s often those things that bring life its pleasure. I say, wear the handmade Italian sportcoat; wear the beautiful scarf; wear that amazing raglan coat to the park with your kids. After all, clothes are made to be worn by people who are alive, and what seems so certain today has been shown to be less stable than we think.
   
2. Tailoring is still flattering. This is still true today just as much as it was three years ago. One of my primary motivators for wearing tailored clothing is that whether I’m fresh off Whole 30 or I haven’t worked out in a month, tailored clothing strikes a consistent and attractive silhouette. It can absorb those small weight fluctuations we all experience throughout the year. It’s my confidence boost when I’m out in public. I think it’s one of the most flattering things a guy can wear.
   
3. The longevity of tailored clothing’s style can’t be beat.
   Despite everything, there’s nothing equal to the staying power of coat-and-tie for a man. Yes, dress codes at workplaces and places of worship and in public life in general are much more lenient for most people, but culturally we still expect our presidents to wear a suit and tie. And actually, that’s cause to rejoice in some ways. As Buzz Tang of The Anthology said to me last year, “That’s exactly how tailoring should be molded in modern lives—it’s a matter of choice, of attitude. If we were living in the ‘30s or ‘50s, us tailored menswear geeks wouldn’t be cool cats. We’d just be normal people because men all had to wear suits in public life. If couture and streetwear didn’t exist, tailoring people wouldn’t be cool.”
   
4. It’s satisfying to wear something that requires the skill that a quality tailored piece of clothing does.
   A tailor must train for a decade or more before they begin to fully understand how to take two-dimensional cloth and make it into a striking three-dimensional garment that flatters. And designers—whether a creative director of a ready-to-wear brand, or the tailor him or herself or the owner of the bespoke sartoria—communicate art through cloth and cut and design choices. The wheat can be discerned from the chaff by the resulting garment’s aesthetic appeal. Yes, there are cheap suits, but even mass-produced garments can still be made to fit and look good, if the designer and manufacturer are aligned in a pursuit of quality fit and aesthetic. It’s the same appeal that a mechanical wristwatch, a well-designed car, or well-decorated interior space all have.
   
5. Tailoring is flexible enough to handle your personal preferences.
   To look really good in tailored clothing does require some homework in coming to understand the historical traditions that inform the “rules,”¹ but once you have a working knowledge of those, “tailored clothing” as a loose genre is a large enough sandbox to play in. You can probably find a way to express your personality quirks and preferences within the realm of good taste. And having those sandbox walls actually makes the process of experimentation much less fraught, because at worst, you’re still more likely to be more “dressed up” than most of the people you’ll run into. The fuddy-duddy connotations of tailored clothing, in fact, usually come from people who are too rule-bound. Add in those more contemporary takes from ALD, for instance, and you have lots of room to try and experiment.

So those are some reasons why, in 2022, I’ll still be wearing tailoring. How about you? Are you going to swim against the strong current of casual dress, going your own way and rock a sportcoat no matter how many people ask when your interview is?

¹Two resources for you to learn more about those rules: One is my eBook. It’s accessible, instantly available digitally and inexpensive. Second is the book Dressing the Man by Alan Flusser, which is the definitive tome on what I’d call dressing with “good taste.” Most of what I mean when I say the “rules” comes from this book and it is the best foundation to build on. ^back