Why Tailored Clothes Are Still Exciting

“I think it’s nice to wear a tie out and about more often, even just like going to the movies,” the sales guy at J.Crew said, and I was in total agreement. It was about 2009, and I was looking at a mid-gray wool tie with diagonal light pencil stripes. The Ludlow suit and all its attendant accessories—like that tie—was taking the world by storm. The heyday of tailored clothing as the thing cool guys wore was in full swing, and I was right on board.

Six years ago, guys were walking around cities like San Francisco (not a place known for style) in Italian suits and leather-bottom dress shoes. Article after article was written about the return of the coat and tie. J.Crew rose to prominence as the mass market purveyor of the smart contemporary suit look, while up-market, luxury brands were popping up offering full-canvas suits and sportcoats. Many a blog was launched in that golden period of tailoring (including mine), many of them on Tumblr (including mine), and many of them are still around (including mine, ha!).

Those days are gone. Tailored clothing has, for the cool kids, been replaced by hype streetwear—Rubchinskiy, Supreme, etc.  Some of the greatest menswear Tumblr’s are all but deactivated. Brands launched in that peak, if they’re still around, pivoted to stay relevant and fresh (Ovadia & Sons is the poster child for a 180°; Eidos transitioned from tailoring-heavy to sportswear to Indian pajama pants in 4 seasons).

But I’m still wearing Italian tailoring and leather-bottom shoes, and excited enough about clothing to be writing a blog about it. Why? And why do I think you should take an interest in it, too?

1. The longevity of tailored clothing’s style just can’t be beat.
   Despite 30 years of New York Times articles proclaiming “the death of the suit,” there’s still no equal to the suit for communicating seriousness and respectability in dress 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.
2. That longevity of style is a comforting and dependable place to be.
   Keeping up with the hype streetwear trends requires a lot more effort than establishing a tailored wardrobe and figuring out how to mix patterns on shirts, jackets and ties. True, the cut and design of tailored clothing has fluctuated over the decades (think the wide lapels of the 1970s compared to the narrow lapels and ties of the 1960s), but those design changes seem to be taking place slower these days. And it is possible to strike a middle ground in design that will age more gracefully.
3. Tailoring is flattering.
   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.
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 well-designed car, or iPhone, 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,” 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 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.

Even though the trends have moved on from a focus on tailoring, one of the great things about the time we live in is that almost no matter what you wear, most people won’t give you too much guff for it. And particularly if you’re dressing up slightly, in most situations that’s a boon.

I’m still wearing sport coats to the movies, and I doubt I’ll stop any time soon.