Reluctant Dressers are easy to spot. They're men who don't care anything about clothes, men who only dress up because they "have" to. (The Reluctant Dresser is usually someone who is forced to wear a jacket and tie for his job; this is different from the Amjack, who tends to "dress up" in his personal life only when he "has" to, but who will then forgo the jacket and tie because no one is making him wear them. Professional Reluctant Dressers are often personal Amjacks, so this distinction is more about the same people in different roles than it is about different people entirely.)
Spotting a Reluctant Dresser is easy; they're everywhere nowadays. Take a look at this picture of the young politician from my previous post about proper dress shirt colors; he's as perfect a specimen as you could want.
A Reluctant Dresser wears:
1. Deadly dull dark single-breasted suit, usually black (which is inappropriate for daytime wear) and either solid or with an almost imperceptible pattern.
2. Dark "dress" shirt in completely inappropriate color like black, red, purple, dark green or dark blue.
3. Jacket sleeves too long to show any shirt cuff with arms at sides, and often long enough to reach his knuckles.
4. No pocket square.
(We can't see his feet, but I'd bet $100 he has the other signs of a Reluctant Dresser.)
5. Pants two or three inches too long, puddling around his shoes. Not cuffed unless the factory inseam already came that way.
6. Cheap, glued, leather-soled, duck-billed black "dress" shoes, often slip-on (which are too casual for a suit.)
7. Mid-calf (too short) dress socks, which you'll see if he sits down and crosses his legs.
Bonus: Reluctant Dressers don't always do this, but the really clueless ones button the bottom button of their jackets, like this guy has. That is never, ever supposed to be done, and that should be such common knowledge that is shouldn't need to be said.
To show how far we've fallen in a couple of generations, this reminds me of when my friend's cousin posted a link on my friend's Facebook wall to her new photo album from Easter or something. I clicked through and glanced at it out of curiosity. Her husband had his bottom button open on his suit jacket, as he should. Some girl he knew posted a comment on one of the pictures, asking him why he left that button open. He responded: "I think you're supposed to."
A. How can she not know that and even have to ask, despite being a woman -- I believe women leave theirs open too?
B. How can he not know for sure, where he says he "thinks" he's supposed to?
It's like neither of them have ever seen a man in a suit before.
For those of you who are fans of Howard Stern, another example is Ronnie the Limo Driver. He wears dark, shiny "dress" shirts, but more importantly, he always wears a dark, plain, single-breasted suit. He's admitted to being a Reluctant Dresser; Howard makes him wear a suit to work because he's their security guy, and he'd rather dress like a slob/overgrown 10-year-old, like everyone else on the staff.
Aside from the dark, shiny "dress" shirts, it's not that there's anything wrong with dark, single-breasted suits or black shoes on any given day; it's that Reluctant Dressers always look dull, and always look the same from one day to the next. A person who loves clothes wants to have fun with them; what fun is it to always look the same? More sophisticated dressers wear suits of varying cuts. They mix lighter blue and gray suits in with the darks, and they mix brown, tan and olive green suits in with the blues and the grays, as well as white or seersucker suits in the summer. They mix bolder patterned suits with the plainer ones. They always wear pocket squares. They wear brown shoes, as well as patterned or off-colored socks, at times. They blend patterns, textures and colors between their suits, shirts, ties, socks and pocket squares. They have fun.
You have fun too. Strive not to look like a Reluctant Dresser.