2. Remember that your style is what you are actively saying to other people. How you present yourself to others matters, no matter how many times you hear "it's what's on the inside that counts." That may be true (I certainly believe so), but who you are on the outside also gets a say, especially to people you aren't familiar with.
3. Dress appropriately for the occasion. No jeans at a wedding and no shorts in the middle of winter. And please, no black socks at the beach (European guys: index and middle fingers pointed at my eyes, now pointed at you).
4. On the subject of socks, most guys have WAY too many pairs of white tube socks. You need 2 pair. Get rid of the rest and invest in some black, brown, beige, and, if you can rock it, red socks. Never wear white socks with sandals/flip flops unless you are in a traditional Japanese kimono.
5. White jeans can be worn, but not with white shoes, not on a cold day, not on a rainy day, and not with colored underwear. And for the sake of baby Jesus, never go commando with white jeans/pants.
6. Matching is a basic element of style. Sophisticated men know when to match and when not to. Every man should know that matching everything makes you look like a pimp. In general, belts should match shoes and ties should match pocketsquares. However, rules are made to be broken - just do so consciously. Stripes on stripes is only for experts, and even then I'm not 100% sold. To see men who are breaking such rules, with varying levels of success, check out the book "Gentlemen of Bacongo":
http://www.trolleybooks.c
The Yellow Man of North Beach gets a pass.
7. It's better to make sure the clothes you buy fit first, before you buy them. Alterations are expensive, so avoid them if you can. All suit jackets and pants must be altered. For jackets, cuffs should end at the wrist, not below it. Ask your tailor to bring in the sides of the jacket so that there is a V shape to your torso. Pant hems or cuffs should end anywhere between the middle of the back of the shoe to the top -- not higher or lower. Please, either roll up those jeans or have them hemmed. The torn and ragged hem you've created by walking around town with the back of your jeans below your shoe makes you look like you still live at home.
8. Less is more.
9. Accessorize. Most guys fail at properly accesorizing, but often accessories define a man of sophistication. Cuff links, a milan straw hat, ties, a tasteful ring (or a wedding band), a nice watch, a nice pair of glasses all add a nice touch to whatever you're wearing. Bling is good. However, refer to number 8. And on the subject of hats: hats often signal to other people that the wearer is ashamed of his thinning hair. Wear a hat if it's cold and misty or if you are out in the sun (or if you're at a baseball game - Go Giants!!) But don't wear a hat if your intention is to fool someone. They are not fooled. Unless they are completely shallow, if they are being nice to you it's because they don't care what's under the hat. So take it off.
10. Shoes matter. Big time. For what a nice pair of shoes look like, Google "Allen Edmonds." Square toes will make you look shorter, rounded toes will make you look the size you are or taller.
11. By all means, flaunt whatever sex appeal you have. Don't be afraid to unbutton that top button or wear shirts that actually fit your body (most men's dress shirts are way too baggy). Just remember, it's a fine line between a little sex appeal and a lot of "Chester the Molester."
12. Although rule number 8 is golden, layering can add sophistication and individuality to an outfit. Layering clothes says to others that not only are you creative, but you are warm. Cold guys are putzes.
13. Guys -- a touchy subject: hair. The subject is unavoidable. Yes, it matters. It matters even to men who are losing their hair. My feeling is that it's not how much hair you have, but what you do with it and if it looks right on you. A lot of guys are bypassing a little hair loss with the Mr. Clean look. Okay, that's cool. But balding men with clean and neatly cut hair can also look mature, which is how a man should look. Unless it's an essential part of your overall style, an adult male should not be walking around with a faux-hawk, nor should a balding man grow out the sides so that he looks like Riff-Raff from Rocky Horror Picture Show.
Beware of the product!! Product is meant to hold, not to be seen. The exception to this is the sculpted Don Draper/Mad Men look. In that case, invest in a good pomade that washes out easily and use a strong hair spray sparingly to keep it all in place. The other exception is if you are currently one of the cast members of Jersey Shore, and you are getting paid to look like a douche. Otherwise, don't get pwned by hair gel gone wild.
Take care of your hair. Unless you are using a lot of product, you don't need to wash it every day, especially if all you ever do is sit at a desk. Even if you work out, a good rinse with warm water is sufficient. Your hair stays healthy and soft when the protective oils coat the hair strands. Excessive washing strips your hair and skin of your natural oils -- especially considering most shampoos are made of heavy-duty detergents.
14. You don't have to spend a million bucks to look like a million bucks. A pair of polished black shoes, basic blue jeans, a basic, white, button down dress shirt rolled up slightly at the sleeves and a subdued wristwatch is plenty. "Fast Fashion" stores like H&M, Old Navy, Zara, and Gap are great for some things, but they are often cheap because of the quality of the materials and the clothes are made for current trends, rather than longevity. A decent dress shirt will cost you anywhere between $85 (Macys) - $200 (Thomas Pink). But only suckers pay full retail, right? So, know what you want/need and keep your eyes open for sales. Better yet: Nordstrom's Rack.
15. Relax. No matter how well you're put together, an angry or uptight man is never an attractive man. Confidence is not being overly assertive, but rather kindness to and respect for others are the true signs of a confident man. Your clothes may look like a million bucks, but your attitude may be saying "trailer fabulous."
16. Finally, dress nice because you want to. Yes, it's important to have a dignified presence to others, but in the end it's your life. Clothes won't change what you are, but they can help communicate who you are and how you wish to be perceived."
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