Details Magazine (highly recommended by the way) has a section in every issue where they have top designers give their "rules of style for men". Interesting read and viewpoints on a number of topics.
KENNETH COLE
The designer with a conscience on how to make the right impression with your clothes
1. Clothing is maybe the single greatest form of self-expression. Whether you're fashion-impaired or fashion-inspired, I urge everyone to take a few extra minutes every day to contemplate the message you’re sending to the world.
2. If you wear a fragrance, make sure it doesn't arrive before you do and linger when you're gone.
3. Few people get dressed up today. Mix dressy with casual or rugged with refined. And one item should be more tailored. For example, if you're wearing a T-shirt, wear cleaner jeans. Wear a blazer with the jeans or a casual top with slacks.
4. Beyond any other accessory, shoes will have a very significant impact on how you look—they make the whole outfit come together. There's that old adage that before you judge somebody you should walk a mile in their shoes. Then if you don't like them, you're a mile away and you have their shoes. What you wear below the ankles is critical.
5. Establish a uniform, then layer in something new to make it fresh each day. I always have my white shirt, my jeans, and my boots. Then I mix up the rest. Some days I wear a graphic tee with a white shirt and a vest. The next, I might wear a white shirt, a V-neck sweater, and a pin-striped blazer. But the must-haves for every wardrobe are a white shirt and a comfortable blazer.
6. When all else fails, wear black.
7. Vests are the accessory of the season. They look great as an element of sportswear or with a suit—as long as they're not matching. It's about breaking up the suit and then wearing the pieces as separates. The jacket, with or without the vest, can be worn with jeans. The pants can be worn with sneakers, T-shirts, and hooded sweaters.
8. Patterns, like stripes, need to be very subtle. The message overall should be that you're not wearing a matched wardrobe (or on parole). Contemplate wearing a jacket that doesn't match your pants and a shirt that matches neither. Your belt and shoes don't have to match either, but there needs to be a sense that everything works together.
9. You've done a good job if people see you and say, "You look great," as opposed to "Where did you buy your shoes, and how much did you pay for the jacket?" Your clothing choices should help present you.
10. No matter how long it takes you to get dressed, it shouldn't look like it took more than 10 minutes.
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TOMMY HILFIGER
The all-American designer on why fit, quality, and the pursuit of preppiness never go out of style
1. Less is better. Even if you have a lot of accessories and a large wardrobe, you don't have to wear them all at once. Wear one stylish item at a time—the others should be fairly basic.
2. Have a light touch when it comes to color. Maybe start with just a tie or a shirt. You don't want a colorful shirt, jacket, and pants. You always have to have a balance color, like black, navy, khaki, or white, to temper the brighter tones.
3. Too much pattern is a disaster. Tropical-print shirts are for the tropics. And flip-flops are for the beach.
4. The best thing a man can do is be true to himself and be classic without being boring. The worst thing a man can do is overdo it—trying too hard is a big no-no.
5. I'm biased. I believe preppy is the way to go. It references old-world charm and conjures up every icon from Robert Redford to James Dean. We should be proud of it. There's a comfort to preppy. When done well, with great quality, it looks like a combination of Italian and English.
6. Quality always wins. If you're wearing something of incredible quality it will outshine any trend, any fashion idea, and anything that's funky or groovy.
7. On a suit, if the sleeves are down to the knuckles or substantially above the wrists, you know it isn't fitting well. And then there are the shoulders. You don't want to look like Herman Munster and you don't want to look like Pee-wee Herman. If you button the top button or center button of the jacket and it's not pulling around the waist and the vents aren't spreading but it's still snug, you know you have a good fit.
8. Before you leave the house in the morning, use a lint brush and make sure you're well-groomed. You can have the greatest clothes in the world, but if you have cereal in your teeth and a bad haircut, you won't do the clothes justice.
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GIORGIO ARMANI
The Italian fashion maestro on holiday attire, the secret to staying young, and the starter suit.
1. When choosing a suit, a man should look for something that he can wear, and not something that will wear him. In other words, elegance, sophistication, and timeless style are always better than of-the-moment trends, which will date—and date the wearer.
2. As for style, a two-button suit is more timeless than a three- or a one-button. A single-breasted is more versatile than double—allowing you to dress your suit up or down more freely and use the jacket as a separate more easily.
3. The most important thing is to feel comfortable in your clothes. If you feel comfortable, you will feel self-confident.
4. The worst sartorial faux pas you can make is looking like you’re trying too hard. To develop your own individual style, really consider what suits you.
5. If you remain curious about the world, you will stay young at heart. Beyond that, I recommend an hour’s exercise every day and a healthy diet with a lot of fresh vegetables and fruits.
6. The holidays mean a handsome velvet tuxedo jacket. If you’re entertaining at home and feel like it, you can try one in a midnight blue or deep plum and you should wear velvet slippers. If you go out, wear shoes—preferably wing tips.
7. When buying a suit, go for a color that will not date too soon, like a mid-tone gray or a black.
8. At black-tie events you can get away with a jacket that has a bit more of an extreme line, something that’s really fitted. And you can never go wrong wearing a clean white shirt.
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JENNA LYONS
J. Crew's creative director
1.There's nothing sexier than a blazer, a tie, and jeans. And yet most men can't put it together; they either end up with a suit and tie or jeans and T-shirt. Try taking half from one look and half from the other. Chances are you'll get something a little bit cooler.
2.Men don't shop enough. Being current has everything to do with finding the place you want to shop, whether it's J. Crew or Tom Ford. You have to get off your duff and get out there, because styles evolve. Certain things are classics and they do stay, but men need to keep updating their wardrobe, because change is subtle. For example, denim is getting slimmer. If you're wearing jeans from two years ago, they probably don't look current. Get a new pair of jeans.
3.Overplucked, overdone men are frightening to me. Women want a man who looks like he takes care of himself but doesn't look like he thinks about it more than she does.
4.A pressed shirt signals work mode. But a washed-cotton shirt automatically makes you feel more touchable, more approachable. It's effortless. However, if everything is washed—that's not interesting. When washed is paired with a blazer and a tie, it looks amazing.
5.Most men don't have a clue about tailoring. They hate to ask for directions and they hate to ask if something looks good on them. Learn to ask the salesperson. Ask a woman. Great tailoring always makes guys look better.
6.Get dressed, then change one element. With a suit, wear a pair of Converse, or take off your dress shirt and put on a chambray button-down instead. You can also do the reverse. Try khakis rolled up with wingtips. Tweaking one thing is an easy way for guys to modernize an outfit, even if they don't know what the hell they're doing.
7.What women notice are the shoes and the watch. Go for understated elegance, whether it's a vintage Rolex or a classic Timex or a watch that was your grandfather's. It's the same with shoes. I love a pair that look like they've been resoled 10 times.
8.A giant shirt is not cute. If it feels overly comfortable, it probably doesn't look so good. A simple fit test is to check your shoulder seam. It's designed to be on your shoulder line—not somewhere near it.
9.We don't need you to be perfect. What we do need is for you to look a little bit more pulled-together. And no pleats, please, not ever, ever, in your life. Ever.