I don't think I've ever seen anyone who didn't look good in a white button-down shirt. I don't mean that see-through polyester thing that's been hanging in your closet for the past 15 years. I'm talking about a nice, white oxford cloth button down. It's a classic look that will never go out of style and looks good whether dressed up with a pair of dress pants or dressed down with jeans. As long as you get one that fits you well, you're set.
2) Black turtleneck
Everyone looks good in a turtleneck—this can't be debated. And as we all know, black can be slimming. If you're a little thicker than the average guy, go with a mock turtleneck. You'll still get the same benefits, but you'll be able to breathe while not looking like a stuffed sausage. They're great when you need to layer, and can even dress up a sweatshirt.
3) Dark jeans
Notice I didn't say "black jeans." Nice fitting, dark-blue jeans look great when you're going casual to a football game and also dress up nicely at the office. The low-riding, washed-out jeans with fancy designs on the pockets just make a guy look pathetic. Don't give in to what the hot salesgirl says; if you're 35 or older, always go for classiness over trends. What you can ask her opinion on is the fit. Make sure you're not buying them too big and roping them off with a belt. It may sound obvious, but to look good, you must buy clothes that fit.
A peacoat could be considered winter wear, but it definitely gets cold enough in early November to need one. This is a classic piece of clothing that oozes with confidence, manliness and class. I mean, the guys in the Navy introduced us to the peacoat, and they're tough SOBs. While the popular designers can charge a lot for one, you can still find them reasonably priced with a little effort. I picked one up last year for under $200 and it quickly became one of my favorite things to wear. It's hard not to feel like a man while wearing one of these.
5) Dark V-neck sweater
Few things are more flexible than a dark V-neck sweater. You can almost get away with wearing one anywhere, which is awesome. If you're a little hefty, make sure the material isn't too thin or you're going to introduce innocent victims to your belly button and nipples. We don't need to see that. Also, wear a collared shirt or a nice t-shirt under the sweater to avoid that "Sopranos" look. In a perfect world we'd wear cashmere, but who the hell can afford it?
6) Leather jacket
James Dean, The Fonz, and Daniel Craig have looked hot while wearing a leather jacket, and so can you. They're iconic, scream confidence and are great for dates and hanging with the guys. Just remember, leather isn't right for every occasion. You should never wear one with a tie, to a job interview, or with athletic shoes. (That goes for you, too, Jerry Seinfeld.) Also, unless you've been hired to front Judas Priest for a reunion tour, never go with a full-length leather jacket.
Yes, you should be wearing a watch—and no, relying on your mobile phone to tell time isn't good enough. A watch is a great way to finish off your look and can make you look like a guy who cares about the details—even if you don't. But please, nothing with a rubber band (unless you're exercising). And it shouldn't be so big that it makes you look like you're trying too hard. You don't need to own a lot of watches, but it's a good idea to have one that's more casual and one you can wear in dressy situations.
8) Charcoal suit
How long has it been since you last bought a suit? If you're like most guys, then it's been way too long. I'm not advocating owning one for every day of the week, but you should probably buck up and buy one every five to seven years. If it's time for a new one, go with charcoal. Unless you're a guy who needs to wear a suit to the office (if so, my condolences), you'll probably only wear one a couple times a year. While some will argue that navy is the way to go because of its flexibility, I contend that charcoal is the better choice. It's darker so it'll make you look a little slimmer, you can snazz it up with just about any cool tie, and it works much better than navy for funerals.
9) New wallet
I know it makes no sense to spend money on something that pretty much just holds … your money. But, face it, it's time to give up that Velcro disaster you've been hauling around since the Clinton administration. You should be buying a new wallet every couple of years instead of holding on to that thing like grim death. A nice dark brown or black wallet that holds everything you need (not everything you own) will be just fine, and again, it shows that you care about the little things. It also illustrates that you have a little class as you pick up the check when taking your in-laws or boss to dinner. While you don't need to spend a lot, the wallet also shouldn't be sporting an NFL logo on it, either.
10) A haircut
File this one under good grooming. Even if you're not the best-looking guy in the world and aren't built like Terrell Owens, you can still pull off a good look if you take care of yourself. A big part of this is grooming—and cutting your hair is a start. If you keep your hair relatively short, make sure you get it cut about once a month. A good way to keep on top of this is to make your next appointment with your barber as you're paying. During your next cut, have your "stylist" also trim the nose and eyebrows, and check the ears for those nasty hairs that crop up about the same year you start suffering from acid reflux. Remember, it's not about being trendy, it's about looking good.By Craig Playstead