The late Hardy Amis. At work? Or at play?
With those thoughts by Mr. Amis in mind, let's talk about that elusive sprezzatura (a word so overused these days that it is losing any meaning at all). Ideally, you want to strive for an unstudied, relaxed look, regardless of how dressed up you might actually be. Clothing that looks lived in, along with a relatively carefree demeanor from the man wearing the clothes, suggests absolute ease and comfort both internally and externally. Think Cary Grant, David Niven, or young Sean Connery here. In other words, you'll want to avoid perfection in your attire, which can make a guy seem too self-conscious about getting it right where his clothes and appearance are concerned. After all, you don't want to look like you've agonized over your clothes for hours before finally putting them on.
So, try these tiny suggestions for a less tightly corseted look, which too many guys out there associate with dressing in anything other than cargo shorts and flip-flops. Extend the life of your dress shirts and don't starch the collars and cuffs. That will lend an instant, softer look and feel to your appearance. You might also consider forgoing collar stays. In addition, don't iron your shirts. Instead, just toss them into the dryer with a fabric softener sheet, so that most of the huge, ugly wrinkles come out, but the shirt does not look perfectly pressed. Be sure to hang 'em up when the dryer signals that the cycle has ended though. By the way, the natural warmth from your torso will help any remaining small wrinkles disappear before long. This method works especially well with oxford cloth button-down shirts when worn beneath a blazer, or a tweed jacket for those colder months, during the weekends.
Add a pair of comfy corduroy pants or chinos that you've had for a while, some slightly pilled argyle socks, along with well-worn penny loafers, and you're all set to run a few errands midday on a Saturday before meeting that new special someone for a drink at your favorite watering hole, for instance, and then taking him or her out to supper afterward. Crewneck wool sweaters and knit ties in muted colors also fit in well with this particular "relaxed" aesthetic, which is still a far cry from sweatpants and over-sized t-shirts. The best part is that you'll look very pulled together, yet extremely casual for your weekends and off hours. Oh, and clothes like these are extremely comfortable too. So, it's a win-win situation all the way around.
What about those times when you must dress with a bit more care, during the work week, for example, or before special occasions? Well, for starters, don't fiddle with your necktie for 20 minutes in front of the bathroom mirror each morning, trying to get it absolutely right with any one of the myriad of complicated knots that exist. Opt instead for the plain old asymmetrical four-in-hand knot. Easy to do and classic. And if the dimple is a little off, or the rear blade is a bit long one day, so be it.
Don't worry about matching your socks to your dress pants exactly either. Dark green, dark red (maroon), or royal blue to-the-knee dress socks make a nice departure from the usual charcoal, navy, dark brown, or black. Likewise, don't worry if there are a few wrinkles in your suit pants or pairs of odd dress trousers or the elbows of your suit coat or sports jacket. Sit down (ease the knees a bit when you do though to avoid stretching your pants out of shape at the knees), cross your legs, and bend those elbows as you lean in across the seminar table to make your point during that 10am meeting. Only department store mannequins stand around all day doing nothing but smile and without wrinkling their clothes. But you're a living, breathing man, not some mass produced, molded abomination in white, tan, or silver plastic. So, put your clothes on, forget about them, and march forth into your day with confidence.
A word of caution here. Everything you wear should obviously be clean. While classic menswear should look lived in rather than brand new, I'm in no way suggesting that you leave the house wearing rumpled, threadbare, chocolate and mustard-stained gear. Your new "adult" clothes should be worn more than for the occasional wedding, funeral, or job interview, so put 'em on for the love of Pete! You can't very well kick up your style a few notches if you shy away from wearing the things you've added carefully to your wardrobe over the last year or so. Get it? The sort of timeless male attire we are talking about here is meant to be worn and enjoyed.
Finally, don't fret about matching your clothing and accessories too closely. You want to come across as casually unconcerned about your appearance. Let's call it sartorial insouciance if a label is absolutely needed. And one more thing. Contrary to what a lot of menswear stores, outlets, retail websites, and formal wear rental places might have us believe, your pocket square should definitely NOT match your necktie. Compliment it in some way, yes, but certainly don't contemplate purchasing a matching necktie and pocket square set. Ever. You don't want to look like a male extra in a community theater chorus line, or some unfortunate android posing as a groomsman in an overblown wedding, do you? It's much better to be a bit absent-minded about it, almost as if to say, "Oh, that old thing? Nope. I didn't even realize it was in my jacket pocket."