I travel a lot for work. This, by the way, is neither sexy nor glamorous, in case you were reading this and thinking, “Man, I wish I could travel for work? That sounds great!”  Unless you travel to London or Maui for work, business travel’s a sucky way to make a living.  But back on point…

Most people I notice traveling for work are men, mostly men over the age of 35. And I’ve noticed a common thread that binds just about all of them together – that they simply have given up giving a shit about having any sort of style whatsoever. Whether it’s the businessman in the oversize, rumpled suit and cheeseball tie on his way to a meeting, or the vacationing businessguy cashing in his miles while “stylin’”in oversize golf shirts, baggy cargos, faded Margaritaville ballcaps and Crocs. These men may be over 35, but it doesn’t mean you’re out of the game and you can just give up on being a stylish guy.  What these guys need to remember is that having style doesn’t have an expiration date; it’s not cottage cheese.  Regardless of your age (unless you’re 80, at which point you get a kitchen pass for the rest of your days on Earth), how you present yourself speaks to your personal pride, your confidence, what you stand for, how you expect to be treated.

I know a lot of really wealthy guys who dress like crap. If you’re really successful, I guess you can do whatever you want and I have less to offer you than you do me, like maybe a few hundred thousand bucks of walkin’ around money, if you would be so kind. But the rest of us still trying to build and maintain a nice living for ourselves and our family, like most of the guys I see when I travel, should still realize that their image speaks to how the rest of us see you. Like everything else we advise on Be Better Guys, bring you’re A-game to everything you do. That’s how you get advantages in life. 

The Two “A”s – Age Appropriate.  I know many guys still see themselves as 26. Hell, I know I do.  But I’m not.  Now I’m not callin’ you middle-aged, but I am saying that guys who are 44 wearing tight-fitting, printed tees with a trim sport coat, ripped premium denim jeans and tennis shoes (like the guy sitting two rows in front of me right now) look like they don’t deserve any respect from anybody. They look like they’re trying too hard. They look like they’re so completely on-the-make that no 23-year-old girl is safe from a guy who could be her dad trying to put the slick moves on. Ever see a mom dressed like she’s trying to upstage her teenage daughter and you think, “Yeah, she’s pretty hot for a mom, but foul!  You’re a Mom, for chrissake!” Guys make the same mistake. You’re two decades removed from college, time to step it up, Pops.

Your Stuff Should Fit, Even If You’re Packing On a Few.  Part of the “I don’t give a crap” look that I see in over-35 guys is that their clothes hang off them almost as poorly as they do their 15-year-old next-door neighbor who cuts the grass with a can of Full Throttle in hand. Now it’s the blousy golf shirts and the my-diaper’s-full, baggy khakis instead of the oversize t-shirts and saggy jeans the teens sport. Look, giant clothes make you look even bigger than you actually are, and I’m readily acknowledging that most over-35 guys ain’t built like they were at 23. But you should still tailor your clothes for a good fit. You’re making decent money now; spend it on a tailor to trim your big-butted trousers and take in your carnival-tent dress shirts. Or better yet, maybe you should buy a size down from what you usually purchase. You don’t have to go skin-tight, like some suburban moms do, but get rid of the baggy stuff and buy clothes that flatter what you do have. Brooks Brothers, for example, has dress shirts in slim fit.  If you’re not portly, try one on. They are more flattering and take fifteen pounds off your appearance.

Conference-Wear, It’s Just for Conferences, Guys.  Look, when you’re over 35, you probably have to go to conferences for work, maybe even do some prison time actually manning a booth.  And when you do, you are usually asked by your company to take one for the team and promote the company by wearing the standard-fare corporate polo. Fine, just take the sucker off when the conference is over and it’s time to go out with the team so you look less like a billboard. There’s usually a break between when a conference ends and the nighttime parties begin.  Go back to your room, check your email, call your gil and put on something that a stylish, self-respecting man would wear.  A regular polo, or button-front shirt, or something that isn’t advertising your company is what I’m talking about.  It just looks JV to be standing at the bar in a non-work setting with your company’s name plastered across your manboob.

No Business-Like Shoe Business.  Forgive our repeated reminders about shoes, but there are lot of folks in this world, men and women, that look at shoes to determine a man’s worth. Fair or not, it’s what some people do. But a lot of men step out with scuffed and banged up and it looks completely careless.   Well-shined shoes do complete a man’s look, the way waxing your car gives it that extra pop after a wash. Next time you’re on travel, take ten minutes and visit the airport shoe shine guy.  Go once, you’ll be way too impressed with the like-new appearance of your formerly worn down kicks that you’ll never let your shoes get that raggedy again.

Deal With Thinning Hair the Right Way. Lots of guys over 35 start losing it. Their hair, that is. But what I see a lot of over -35 guys doing is growing lots of hair around it to cover it up, combing it over the bald spot or growing length on the back and sides to compensate. That’s exactly the wrong thing to do, unless you’re interviewing for a gig at Marshall Space Flight Center, where that look probably got its start. When you’re going bald, you don’t have to shave it all off and do the “cue ball”, but consider keeping your hair close-cropped to your scalp and blend the bald spot in with the hair you have instead of trying to cover it up. A close-cropped cut is more flattering and considerably more stylish than a garden that only grows in patches.

BONUS TIP:  Time for Retirement – The Earring.  Sorry, but you’re not Michael Jordan, who I think also looks like he’s trying to hang on dearly to his 20s by wearing his hoop when he’s out in the world.  I’m on a plane right now with a guy, looks like he’s retired Army, bald, built like a bullet, dressed in Under Armour polo…all fine.  Except there’s that little onyx stud in his left ear and it looks completely out of place.  Because he’s 48.  Just looks wrong.  Time to lose it, fella.

The fact that you’re not a kid anymore isn’t a bad thing.  Once you hit 30, 35, the prime of your life is in full-swing – you might have a wife or a steady girlfriend (or both if you’re really fortunate!), you’ve got some cash to support your wishes, you might have kids, meaning you’re a teacher now and you’ve got eager little people wanting to emulate everything you are (even when you’re standing around on the phone in your boxers).  This isn’t the time to take your stylish foot off the gas.  So stop trying to hold on to the post college look or the beach bum look or the trying-too-hard-to-hang-with-my-teenager look.  You are a full-grown, confident man; you’re not an overgrown boy, and when you elevate your look, watch as you’re treated and received differently, and better, by everyone.   And get a haircut.