Off the Cuff (15 page)

2.
Newsboy caps.
I love the newsboy cap that's become really popular lately.
It's quite fetching on most men and can add a lot of panache. It looks great
with a woven shirt and a sport coat. Just please don't wear these with a tweed suit or you'll look like Mickey Rooney in
National Velvet
.

3.
Knit caps.
You should definitely have a nice warm knit cap for the winter, specifically a skullcap in black, brown, or gray wool. That means it's not a ski hat with a pom pom on the end. Those are best for the ski mountain or for
Ice
Castles
theme night in the privacy of your own home. If you're actually skiing, you're excused, because half the fun of skiing is getting dressed up in the outfit. I also love a hot toddy in the lodge
après
ski. Or a hot David or Billy for that matter.

4.
Fedoras. I fully endorse them and would love to see them come back, but I don't think women will start wearing gloves again either. They look especially great with a suit, but just make sure they're not huge. Okay, here's an advanced maneuver: There are seasonal rules for hats, too. Natural straw (aka
the Panama) is for spring and summer, and beaver (yes, beaver) is for for fall and winter.

5.
Cowboy hats.
The cowboy hat is a personal favorite of mine, hearkening
back to my days as a trick rider on the gay rodeo circuit. Ah, but that was a lifetime and many broken nails ago. It's an American icon, like the cowboy boot. Just be careful it doesn't look like a party favor you'd get at an overproduced Western-themed bar mitzvah. It should be authentic. It should be well worn and weathered, and made of natural straw and not recycled things like tires or soda cans.

1.
Foam truckers.
Avoid the foam trucker unless you're Ashton Kutcher, and he's so darn cute that I'll let him get away with it. The reason that the rise of a foam trucker is so big is so that they can put a billboard on your head, complete with a logo, phone number, map, e-mail address, and store hours. If there's room to print every store location nationwide, your hat is too damn big. In other words? Trucker hats: best left for truckers.

2.
Kangol and hipster hats.
Those funky, updated berets favored by Samuel L. Jackson and the late John F. Kennedy Jr.—are really way trendy and proba
bly don't look good on too many people. Definitely not for amateurs, and best left to Alicia Keys.

3.
Novelty fleece ski hats that make you look like you have dreadlocks or make you look like a pterodactyl. It's a no-brainer, like the people who still wear them.

4.
Any hats purchased while drunk at Mardi Gras. I don't care what it looks like. Just get rid of it.

5.
Do rags and bandanna “drug helmets.” They look good on Nelly, but then again, what doesn't? Chocolate thunder!

6.
Jester hats. They were invented to make people laugh at you. Brilliant invention. Still works!

7.
Hats that combine the art of crochet with the art of recycling. You've seen them at county fairs: shards of old Mountain Dew cans lovingly (or drunkenly) strewn together with neon-colored yarn to create a conversational-but-stomach-wrenching bucket hat. Your green, earth-friendly impulses are to be applauded, but not at the expense of polluting the fashion landscape with ugly headwear. I'm channeling that sad Indian again.

STYLISH ACCESSORIES ARE SO VERY IMPORTANT. JUST BECAUSE THEY'RE SMALL AND GO ON LAST DOESN'T MEAN THAT THEY
should be an afterthought or that you can go without them. Think of accessories as the crowning glory of that wardrobe you've worked so hard to put together: You need to pay attention and not screw them up.

The average straight man's jewelry should be minimal. Most of the time, men and jewelry just don't mix. Unless you've won a Super Bowl, there is no reason to wear a giant dome ring as an homage to your gridiron glory days. Put it in your hope chest or hock it. Chains, rings, anything like that—especially when done in gold—will always make you look like you're in the mafia or trying out for
Kiss Me, Guido
. If you're a young guy, or exceptionally cool, a simple necklace made of a piece of suede cording with a little piece of silver hanging from it—either a small cross or some sort of ethnic token—can look really hot with an open shirt, or with a T-shirt and denim. It's very rock and roll. Very Johnny Depp. Just remember that whatever's hanging from the cord should
never
be bigger than your head or a toaster. Come to think of it, your head shouldn't be bigger than a toaster either.

As for earrings, I'll be honest: I don't like them. For 99.9 percent of men, I think earrings make you look like an out-of-date rock star or a pirate, and neither is a particularly enviable look. In very rare instances, someone like Johnny Depp or Lenny Kravitz can get away with earrings. But for average Joes, I suggest you take that ear-ring out and leave your Def Leppard fantasy at the door, thank you. My motto? Studs without studs.

 

The only jewelry I will unconditionally allow, of course, is a wedding band. That's the kind of sacred ground where I could never say what's good and what's bad. It's so special, and obviously, if you have one on, you've received it before I've gotten to you. Hopefully you're wearing a simple, classic, elegant wedding band, but even if you're not, the person who gave it to you loves you and you still have to wear it no matter what I say. I'll deal.

Because most men don't wear jewelry, thank God, a great watch is really important. Unless you're a gender illusionist (or drag queen, as some people so mundanely call them), a nice watch should be the most noticeable piece of jewelry you own. Your watch doesn't have to be a Rolex. But it shouldn't cost $5.99 and be made of plastic or held together with Scotch tape, either. Think somewhere in the middle of those two extremes. You can get a great watch like a Swatch that's relatively inexpensive and looks amazing. Actually, get two watches: one for work and one for the weekend. When they're classic and sophisticated, they will last you a lifetime. I love a classic diving watch, a chronograph in stainless steel, or for a more dressy option that looks great, a tank watch.

 

Another great trick is to buy a watch with a simple silver or stainless steel case and a
removable band.
You can have a brown leather band, a crocodile band, and even a fun multicolored grosgrain one for summer. It's a great way to get many different looks out of one watch. Versatile. Like me!

 

For the record, I don't mind a sports watch, I just recommend you don't overly trick them out. Your watch shouldn't be able to land the space shuttle or locate a stolen car. It's a watch, not a LoJack.