The real James Bond -- author Ian Fleming, looking relaxed and at ease in a suit and bowtie no less..
1) You must wear your clothes.
Don't leave your good stuff hanging in the closet or folded in your dresser. Put it on. Make a habit of wearing nice things. You'll begin to feel quite comfortable in them fast, which will make you look relaxed and, wonder of wonders, give your clothes that coveted "lived in" look.
2) Don't fret over a few wrinkles.
Barring accidents with food, ink, or blood, once a year dry-cleaning is fine for suits, sports jackets, and odd dress pants. In the meantime, put on these items and take pleasure wearing them. When you take pleasure in using something, you become comfortable with it and considerably less aware and self-conscious about it. Hang your garments up at the end of the day or evening. Let them air out for 12-24 hours before returning them to the closet. If there are a few minor wrinkles on the insides of elbows or the backs of the knees, so be it. Besides, these will gradually lessen as the item(s) hangs in the closet until the next time you pull it out to wear.
3) Avoid standing/moving like a mannequin.
You can always spot the guys who don't wear their nice suits and sports coats-odd pants combos often. They look self-conscious and uncomfortable. Plus they move like the stiff, rusty Tin Man in the Wizard of Oz. Neither are you the Scarecrow with a broomstick for a spine. R-E-L-A-X! Have fun. Sit down and cross your legs. Lean over and rest your elbow on that nearby table or desk. Flop down on the sofa in your office if you are lucky enough to have either. Move like you would in a pair of pajamas or your favorite jeans and t-shirt. A casual, nonchalant bearing will help you and your clothes feel AND look better.
4) Some minor fraying on cuffs and collars of shirts is fine.
It usually takes mine between 6-10 years to develop this subtle feature. Some slight fraying shows that a shirt is loved and not brand spanking new. This is also when a dress shirt is at its most comfortable, and that will translate directly into how you feel and move in the shirt, making you feel at ease in your clothes and helping everything to looked lived in and enjoyed rather than taken out of the closet only for those two or three occasions a year when your mother, spouse, girlfriend/boyfriend forces you to get dressed up. Or the occasion demands it.
5) Instead of ironing your shirts. . .
Toss 'em in the dryer with a few fabric softener sheets, and hang them up when the cycle is over, and they are still warm. They'll look just ever so slightly more nonchalant and less like they've had the life ironed out of them. And on that note. . .
6) Avoid over-starching shirt cuffs and collars.
Some gentle ironing here is preferable if and when you absolutely must looked impeccably pressed, but routine starching makes these parts of a shirt wear out faster. And more important, your shirts will feel stiff and uncomfortable when you put them on. And that will make you feel and come across as stiffer and less natural as you move through your workday or evening out on the town.
7) Don't bother learning fancy pocket square folds.
Unless you are going for that Sean Connery-era James Bond (or Don Draper) TV Fold with a white linen handkerchief. Otherwise, don't fuss with your more colorful silk or wool pocket squares. Just take one from the drawer, stuff it in your pocket, arrange so that a little shows, and forget about it. And don't you dare match the pocket square to your necktie too closely. You risk looking like you bought the two as a set, or (as my wife jokes) like you are part of a high school chorus production.
8) Polish your shoes routinely.
Not only will this help them to last longer and look good, but over time, especially with tan and brown shoes, a wonderfully variegated patina will develop. Black shoes, on the other hand, will develop an increasingly deep, rich shine. And of course, actually wearing those dress shoes will mean that they conform to your foot and develop some slight creasing unique to your particular stance and gait. Once again, don't relegate your good shoes to the back of your closet except for twice yearly wear. They'll never break in that way. Put 'em on!
9) Avoid an overly coordinated look.
The dreaded matchy-matchy approach always looks to my eyes like: a) you're a GQ model mannequin, b) you've left it to a salesperson or personal shopper, or c) your mother still purchases your clothes for you. Not quite the effect you want, is it? Except for the most conservative of occasions -- business, weddings, funerals, or state when simple, understated elegance is (or ought to be) the rule -- I suggest instead always having one item that does not quite match everything else. The easiest things to do this with are neckties, or pocket squares, or sometimes socks. But exercise some care and common sense here because it's all too easy to get carried away with not matching. Why risk attracting attention to your attire because you resemble one of the various incarnations of Dr. Who?
10) Don't fear making the odd little style mistake now and again.
Occasionally everyone gets it a little bit wrong. For example, back in early April, I left the house in a certain pair of loafers that I thought would look fine with a tweed jacket and corduroy pants. Halfway through the day, I realized that those particular shoes most certainly did not, and I felt self-conscious for the rest of the day even though I am pretty sure no one else noticed or cared. Mental note to self: DO NOT repeat that specific combination of clothes and shoes. The point is, don't be so afraid of making a sartorial mistake once in a while that you are paralyzed by that fear. It will show in your face, and in the way you move. In turn, not only will you look miserable, but your clothes will not come across as lived in and an extension of yourself. Know what I mean? Half the battle of looking good in your nicer clothes is feeling comfortable in them. And when you feel self-conscious, you're going to feel and look uncomfortable, whch will be apparent in how you carry yourself.
There we are. Undoubtedly, there is much else to say on the subject of how to achieve that "lived in" look with your attire, but the tips outlined above make for a solid starting point. Average guys working to kick up their everyday style several notches would do well to give them more than a little consideration. Until next time then.