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The Guys’ Guy’s Guide to “Guy’s Guy” Style


They say that men’s fashion is dead. Need proof? Look at all of the retail stores that are closing. Now consider meggings and the man bun.

So where do guys go from here? Studies show that consumers in general have cut way back on clothing purchases since the Great Recession. Between paying off student loans and $17 cocktails, who has an extra $200 to blow on a pair of designer jeans when you can pick up a pair of 501’s on sale for under $50? When it comes to clothes, today’s men are sticking with the proven staples of guydom. But, even when working with the classics, a Guy’s Guy has to add some swagger to make them his own.

Guy’s Guy is comfortable in his own skin. He creates his own personal style whether he’s twenty-five or fifty-two. A Guys’ Guy’s style is confident, understated, and transcends trends and fads. He evolves his look organically with both feet on the ground and his eyes on the prize. Casual confidence, emotional intelligence, and timeless style are all hallmarks of a Guy’s Guy.When it comes to suiting up, he dresses classically and comfortably, with just a nod to the latest styles without being overly trendy. That doesn’t mean he doesn’t know how to clean up and look great in a suit, a tux, or jeans and t-shirt—It simply means that a Guy’s Guy wears his clothes. His clothes don’t wear him.

Looking through that lens, I’ll riff on a few staples of today’s man’s wardrobe from a perspective that’s more classic than couture, more Varvatos than Versace, and more Levi’s than Gucci. You may agree or disagree. It doesn’t matter. It’s just part of an endless discussion of how we express our masculinity in today’s crazy world.

With that bloated build up, it’s time to roll out the first installment of what I’m calling The Guys’ Guy’s Guide to “Guys’ Guy” Style. Let’s open the closet and take a look at some Guys’ Guy’s fashion do’s and don’ts and how to look great without breaking the bank.

1. Outerwear – Ever notice that when guys get together they often hang at the bar with their coats on the entire night? I do that a lot and I’ve noticed that I’m in the majority when it comes to that weird fashion tick. Now, if it’s fifteen degrees I’ll probably take my down coat off and hang it on my barstool. That said, for the most part when a guy puts on his jacket, it stays on all night. So you better chose a cool coat. I’ve gotten lots of mileage out my pea coats, bomber jackets, and denim jackets. It’s always good to have a quality leather jacket too. A beat up, old school motorcycle jacket is timeless. Finding the leather jacket that fits your personality is fun, as long as you don’t get too crazy and go with black floor-length duster or an 80’s maroon Donnie Brasco style coat.  For leather, go understated and classic.

I know a lot of guys prefer those Patagonia or LL Beam fleece jackets. For me, that’s for a weekend of golf or going to a football game. A hoodie under a jacket also works in casual situations, but if the hoodie is too bulky it won’t work for Saturday night. Plus, every Guy’s Guy needs a quality overcoat or raincoat if he’s in a business wear he wears a suit.

2. Hair – The only rule to follow here is to wear a hairstyle or facial hair that’s in sync with the shape of our face and how much hair you still have on your noggin. More and more young guys are losing their hair early due to stress, the environment, and bad-luck genes. The good news is that if have decent shaped head, rocking a super close-cropped style works. Beyond that, be careful with the previously mentioned man bun, or whatever that weird, pull-back thing was that former Jets QB Mark Sanchez did with his headband a few years ago.

If you have a nice head of hair, choose a style that works over an extended timeframe. Unless you’re a working actor, you’re not playing a new role every six months. Find a cut that works and stick with it for a while. In this case, consistency is not a bad thing. When it comes to facial hair, there are no rules. If you think your big bushy beard is really cool, I just have two considerations—How does that big-ass hipster beard feel when it’s ninety degrees? And remember, mustaches were big in the seventies. How did that work out?

3. Tattoos and jewelry – Tattoos is another area where nowadays, anything goes. That said; think long and hard if you have an urge to rock ink above your neck or God forbid, on your face. Call me old school, but as cool as you think a nose ring might be, I can’t help but think about the consequences of wearing a nose ring and catching a weeklong running nose, or the sight of a seventy-year old man with metal between his nostrils. Just sayin’. Earrings are a bit dated now, so unless you play pro ball, do you need to rock diamond studs?

When it comes to jewelry, be tasteful. If you can afford it, you will never go wrong investing in a classic watch. Bracelets are a personal choice, but if you go for it, consider real semi-precious stones with energetic properties, leather, or silver. If you wear a necklace, same rules apply. Make “clean and simple” be your guidelines.

4. Jeans – Regular and slim cuts are fine, but unless you’re in a rock band or are thin as a rail, super-skinny probably won’t look great on you and they’ll crush your balls. And, ladies really don’t want to see your junk bulging all time.

You can never go wrong with dark washes. They work great across the spectrum of occasions, like for business with a blazer, with a hoodie, or with a t-shirt. It’s worth investing a hundred bucks or so in a good pair of jeans made with Japanese raw selvedge. I have a pair that I bought as stiff as a board. I’ve never washed them, but over time they have broke in nicely and look great.

5. Footwear – Kicks are another sartorial category where personal taste and comfort rules. Let’s start with casual. What guy doesn’t have a closet overflowing with sneakers, training shoes, and running shoes these days? That’s all good, but when you’re out with a lady and you want to wear sneakers, make sure they are clean, up-to-date, and lightweight. I love the comfort of New Balance, but until recently a lot of their styles have been kind of clunky.  Classic causal kicks include Timberlands (I have a low cut pair that totally rocks), chukkas, and smart looking, simple boots. For work, make sure your shoes are fresh and kept cleaned up. Also, make sure you match the color of your belt with your shoes. If you wear a suit to work, simply buy quality shoes that are at least on par with your suits, ties and shirts. A tattered pair of shoes really kills the suited-up look. As far as sandals go, I’m for them, but not at the office. I don’t buy into that “mandals” handle. There are lots of cool, comfortable sandals for the weekend or the beach. And do I need to remind you about no socks with the sandals? I didn’t think so.

6. Dressing up – No matter what he does for a living, every guy needs to own a suit, and possibly a tuxedo. When I started out in marketing and advertising, I had to suit up every day and, man it was hot on those subway platforms in August. Thankfully most industries have loosened up their dress codes, so unless you’re an attorney, banker or work in insurance, you probably dress casual to the office. However, “business casual” does not mean t-shirts and beat up shoes.

Even if you dig ditches, you’ll need a few standard items in your closet that fit any proper occasion that might crop up. I suggest that every guy invest in a quality navy blazer, a dark colored suit (preferably navy, gray or black) in a lightweight wool fabric, and a handful of dress shirts that have collars that fit his neck and facial contours. If you buy three dress shirts, consider owning one that’s button down.

I bought a tuxedo in my twenties. I still have it and occasionally wear it. It’s a traditional cut with a shawl collar. And, yes, it’s black. The waistband has hidden notches that allow for changes in my waistline. For the cost of a few rentals you can own a tuxedo, so buying one is a smart investment. Concerning ties, I suggest not too flashy, skinny or wide. And, if you want to be taken seriously, skip the bow ties.

7. Casual shirts (t-shirts, polo, etc.) – Unless you want to look like a bouncer, you can pass on the black, skin-tight muscle shirts. This Guy’s Guy likes polos, and you can never go wrong with an original Lacoste (alligator logo). They’re expensive, but they are made of Pima cotton, made in Peru, and last forever. You can find them on sale and they age well. My only advice on t-shirts is to be careful about the size of the logo or design. Do you really need to show everyone that you are a Denver Broncos fan? And, although I’m not fan of those omnipresent ironic t-shirts, I’m not a millennial. So, for me, solid colors are the best choice. I favor dark colors like navy, gray or black, or good old white. V-neck or crew collar? It doesn’t mater.

I’ve also invested in a handful of denim shirts. You can wear them anywhere, except in my opinion, work unless you are a creative or at a start up. I prefer a western cut and like how the fit of denim shirts from Lucky Brand, Muji, and J Crew. Levi’s makes the gold standard, but I find that they are cut for really slim guys.

8. Summer fun – Shorts are great, but this is another category where you want to keep it simple. Yes, I know women detest cargo shorts, but if you really, really need extra pockets for all of your stuff, I don’t see anything wrong with wearing cargos on a sunny Saturday. I don’t wear my shorts too long or too short and I keep the colors and designs under control. So, although I dig the Rolling Stones, you won’t see me wearing a pair of shorts covered with their lips and tongue logo. That said, a classic white or black Stones t-shirt with one logo works with a pair of shorts or jeans. When it comes to bathing attire, buy a decent bathing suit. Yes, you can wade into the ocean in your cut off sweat pants and tightey-whiteys, but do you think the wet, saggy look is going to attract any ladies? I prefer a bathing suit that comes to your mid-thigh to super long board shorts, and I think most ladies agree. If you live in America, Speedos are for the swim team. Sandals are fine for the beach and trekking around town on the weekend.

9. Hats – Most guys have at least ten baseball caps. I live in NYC and have seen every team logo you can imagine in the subway. I can also unequivocally state that there is no better looking baseball cap than a Yankees cap. Unlike, say, a NY Jets cap, a Yankees cap looks classic and it matches any outfit. Caps in bright colors like the Jets green or Bronco’s orange scream, “Hey, I’m a crazy Jets fan and I might pour beer on you if you look at my girlfriend.” It’s okay to wear a Jets cap and a jersey when attending a game, but what is the message you are sending out when you’re on the street? It’s just something to keep in mind. Again you can never go wrong wearing a New Era traditional navy blue Yankees cap.

For cooler temps, every guy has a woven woolen cap. Most of them are made from 100% polyester, which makes your head sweat and gives you hat hair. I suggest you check the inside label and buy one that is 100% cotton or wool. And, guys, do you really need that sock hat when it’s eighty-five degrees? Just sayin’.

10. Underwear – I used to be a boxers guy. Then I found them to be too bulky for under dress clothes, so I switched to super lightweight breathable body-hugging boxer briefs. They are cool and comfortable and fit comfortably under even slim-cut jeans. Although I prefer going commando once the temperature hits sixty degrees, I wear underwear to work. Believe it or not, sometimes wearing an undershirt under a dress shirt or a polo shirt keeps you cooler. And, it doesn’t look half-bad. This is another one where you can use your discretion and personal style.

The bottom line is a man’s style is a personal thing. There is nothing wrong with rocking out now and then, but for most occasions, it’s better to err on the side of wearing understated clothing. That does not mean boring. It means that the real you will not be overshadowed by your clothes. And remember, the best way for a Guy’s Guy to showcase his style is by being comfortable in his own skin.

Because of the topic, this week’s GUYS’ GUYS OF THE WEEK are George Clooney, Ryan Gosling, Jamie Fox, Jake Gyllenhaal, Daniel Craig (as James Bond), Bradley Cooper, and Tom Ford with a special mention of Steve McQueen. These guys know how to dress up and dress down without ever letting their outfits take center stage.