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dressing with style – rules for beginners

January 21, 2010

I was out the other night with some friends when several of them asked me about style and clothes and how I learned to dress well.  Since how you dress tells volumes about you to the world and espcially to women, it is important to make sure that you’re sending the right message.  Specifically in the area of women, dressing well is a simple signal that you are a man of higher status and that you ”get it” and lowers some of her defenses she would use on a guy that she thinks is lower status.

First and foremost I’m going to be talking about about classic style, not about being trendy.  Why is that important?  Well, classic style is something that is well, classic, and that means that it has stood the test of time.  Trends come and go and too often end up looking stupid in a short time (parachute pants anyone?) and costing you more money as you try to keep up on what’s trendy.  If you buy a more classic wardrobe, you’ll always look sharp, you’ll save money in the long run, and you’ll never go out of style.

The first thing to remember, is that when you are starting out you really need to educate yourself.  As with most things, you need to understand the rules before you can break them, and yes there are certain rules that apply to classic fashion.  I HIGHLY recommend the following book:  http://www.amazon.com/Details-Mens-Style-Manual-Ultimate/dp/159240328X.  There are others, but think of this as Classic Style 101.  Also, Mad Men (John Hamm, John Slattery), Ocean’s Eleven-Thirteen (George Clooney, Andy Garcia), and Law and Order episodes with Jesse Martin are both great shows for classic fashion.  Other people that have great style include Paul Newman, Gene Kelly, Sean Connery, and Humphrey Bogart.  Oh and believe it or not, Phillip Micheal Thomas, Don Johnson’s partner on Miami Vice had some amazing suits.

Here’s a quick break down of the most important rules:

  • Shoes – Women notice shoes very quickly.  My friend Hugh goes so far to suggest that you should spend more an your shoes than almost any other item in your wardrobe except for a suit.  For some reason having nice shoes sends a woman a quick signal of your status.  A bad pair of shoes can ruin a whole outfit.  Do not wear loafers with a suit and do not wear dress shoes with jeans.  If you don’t know the difference, read the book.  A good pair of black Oxfords are the cornerstone of classic wardrobe.
  • Socks – NEVER wear white socks unless you are at the gym. Period.  Match your socks to your pants, not to your shoes.
  • Trousers – Try to stay away from pleats for the most part, or at least keep them small.  They are usually not that flattering for most men since they add lots of fabric and can make you look sloppy.  A pair of well fitted flat front trousers are flattering for almost any man.
  • Belts – Always match your belt to your shoes, and try to stay away from trendy belts.  Giant belt buckles should be left to country and wrestling stars.
  • Shirts – If you can afford to have tailor made shirts, I would recommend it.  The fit will be so much better, and the style will be well suited to you since most tailors can give you a good recommendation.  Also, if you are lean, buy fitted or European style shirts as they are more tapered and will have cleaner lines.
  • Undershirts – ALWAYS wear undershirts.  It will save your shirt from wear and tear and perspiration.  If the shirt is a little thinner, it will keep a clean look especially if you are hairy chested.
  • Ties – Do NOT wear theme ties (Christmas, Star Trek, etc..).  The general rule is that the tie should have at least one color of the shirt in it.  Once you get a feel how to match different patterned ties with various shirts, you’ll come off as having a more sophisticated style.
  • Sports Coat – Having a nice sports coat gives you a more sophisticated look without the formality of a suit.  They can also be paired with a nice pair of jeans and loafers.
  • Suit – Don’t scrimp on this either.  A cheap suit is easy to spot.  Nordstroms is always a safe bet.  Also make sure that you find a good tailor to make sure that it fits well as an ill-fitting suit looks bad and is not comfortable.  If you are smaller stay away from double breasted suits since it will add a lot of extra fabric and make you look bulky.  Also, stick with the classics – black, navy, gray, pinstripe, etc.  Novelty suits are always a bad idea.
  • Coats – A nice wool or cashmere coat will also make you stand out, and keep you nice and warm.  A well-fitted Navy Peacoat is also an option, but is slightly less formal.
  • Scarves – A nice cashmere scarf can add that final touch to an outfit.  A “Where’s Waldo?” red and white number will make you look like a dweeb.
  • If you are younger, you can add some non-classic touches, but as you get older, you should stay closer to the classic styles.  Dressing your age is so much more attractive.  Nothing seems more pathetic than a 40 year old trying to look 25.

There’s a lot more to it, but these are the basics to remember.

A few sites that I recommend to get you started:

  • Dressing for Success, Again is an interesting article that I found about why many younger people are choosing dress better and give up the slacker look.
  • The Impossible Cool is one of my favorite sites of classic styles.  I love this site as it shows how most of the classic styles look so great, but it also shows how you can bend the rules as well.
  • A Tailored Suit is a great site that explains the basics of fit for shirts and suits.
  • Details, Esquire and GQ are a bit more on the trendy side, but most of their looks are from the classics.  Master the classic style, then you can add your own touches to it.

Anyway, I hope this helps get you started.  I’ll be doing some more posts on style in the future, but these are the things that have gotten me started on my path to dressing better.

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