Pushing Forty: A Men’s Style Guide in 8 Simple Rules

imageEver since I met my husband Grant, he’s had impeccable style. I’m not talking like in the weird metro kinda way – I just mean the guy has taste, and good taste to boot. I was raised by an Italian father whose own style made most Americans look like, well, Americans. So I inherently appreciated Grant’s sensibilities around how to dress, and how to dress with a timeless, classic style. So against his better judgement, and possible bribing on my end, he’s agreed to guest blog for me this week on the wake of his birthday (the one before the big one). So listen up folks, I’m looking at you “guy in the graphic tshirt” – he’s only gonna say this once…


As the sun sets on my thirties, I’ve come to realize that a large part of manhood is presenting yourself as a man. You can partially get away with being an idiot in your twenties. Your thirties, forget it. Peoples’ expectations of you triple, and the scope of your responsibilities as a man increases tremendously. So what’s the best way to meet all this head-on? It starts with how you present yourself. So buck up, men, it’s time to get serious.

It’s pretty rare that I make statements on fashion. But I’ve become pretty embittered by the ways some guys my age continue to dress like they’re in high school, including men that I’ve interviewed for work. So whether you’re a corporate exec or a cowboy, a salesman or a soldier, here are a few nuggets of advice to present yourself with some dignity and staying power as a man that’s getting a little older.

Rule #1: The Golden Rule

As a self-respecting man, I only have one overriding rule when it comes to style – I don’t own, wear, or drive anything that won’t be in style ten years from now. Everything else will take care of itself.

Rule #2: Suit Up

If nothing else, own one perfectly tailored suit. It doesn’t have to say Prada or Zegna on the tag, but invest at least a few hundred bucks for the long term. You’ll need it for weddings, funerals, fancy dates, and maybe most importantly, job interviews. Trust me, the investment’s worth it. The jacket should have a semi-snug V-shape through the torso and the pants should be tailored to the shape of your legs. There are three cuts of suits – American, English, and Italian, but the only thing you need to know about them is that they get more and more fitted in that order. Just make sure it doesn’t fit like your older brother’s suit from the 80’s. You’ll know the right suit as soon as you put it on, just from the way it makes you feel – all that will be missing is a 1966 Aston Martin DB6.

A few of my favorites are from Zara and Banana Republic on the lower end, and Hugo Boss and Ralph Lauren on the upper end. These folks can get you in some pretty swanky threads without completely breaking the bank. The suit should be black, dark blue, or gray, but keep it conservative. Steer clear of the NFL announcer pinstripes. It needs to be something that will look at home in a work meeting or at the Oscars. These days, you can’t go wrong with throwing in a pocket square – your sophistication meter will skyrocket. James Bond would nod and grin in approval.

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Rule #3: Good Timing

I’m not a believer in men’s accessories, which leaves a watch as the only way to convey that you’ve got a sense of style even in jeans or board shorts. You don’t have to take a loan out against your mortgage to invest in a good timepiece. If you’ve got the dough to shell out for a Rolex or Panerai, be my guest. You’ve got good taste if you’re barking up those trees. But there are plenty of brands that will look sharp, last a long time, and earn the respect of even the most discriminating watch aficionado for about the price of a new TV.

I prefer Swiss-made watches because I know the quality is there (my Omega Seamaster kept on ticking after more than 1200 hours of dive time), but they’re pricier. Again, keep it understated – gold or rose gold is fine, as long as it’s a classic design. I like a watch that looks at home going to a movie premiere or a thousand feet underwater. Hamilton, Tissot, Shinola, Brera, Oris, and Victorinox are all quality timepieces that fit that bill for a respectable price. And Shinola is made right here in the good ol’ U.S. of A.

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Rule #4: Give it the Boot

On any given day, I’d prefer to be wearing a good pair of boots – cowboy boots, work boots, even combat boots. But if you’re like me, the trick is finding a pair that you can wear with jeans in the morning to the donut shop with the old-timers (whose respect you have to gain in your thirties), at work in the afternoon, and then with a suit at night. That last part’s tough. My answer to that dilemma: the Red Wings Iron Ranger. Timeless, classy, and tough. There are a few boots out there that can pull all that off, but this one’s the gold standard.

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Rule #5: Ditch the Skinny Jeans

Tailored, fine. Skinny, no. This is one of the worst fads in men’s clothing history. I personally rank these up there with wearing socks with sandals. So few guys can pull off skinny jeans that the percentage is what’s called “statistically insignificant” in mathematical lingo. Do you think Steve McQueen, John Wayne, or Sam Elliott would be caught dead in skinny jeans? The World’s Most Interesting Man? Not a chance. Joey Ramone, sure, but let’s face it – most of us aren’t Joey Ramone. Oh, and don’t ever wear anything Justin Bieber wears.

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Rule #6: Graphic Content Prohibited

For the love of all things holy, keep the graphic tees under control. When your kids come of age, it might be tougher to garner their respect with that arsenal of graphic tees in your closet. And by the way, most of them aren’t exactly knee-slappingly hilarious. Besides, nothing says Jersey Shore like an Affliction t-shirt. Remember, part of transitioning into your 30’s should be representing yourself with class, dignity, and uncompromising manhood. Also see: graphic hats, graphic jeans, etc…


Rule #7: Empty Your Tank

Save a guido, donate a tank top. The only place tank tops are acceptable is Southern California, and for guys under 25. That is all.


And one for the road, fellas…

Rule #8: Don’t Feed the Hipsters

If you’re going to grow a bushy beard, do everyone a favor and make sure you’re either a real-life lumberjack or a Delta Force operator straight out of Afghanistan, and preferably not a Hollywood hipster (in skinny jeans, no less). What I’m saying is, be the guy below and show us that you’ve earned that beard.


As for behaviors in your 30’s, well, that’s a whole different post…

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