classic blazer

•  Pants need to "lightly skim" your body,  not hug you tight, such that the pockets flare out when you walk or sit!  They should be hemmed one inch from the bottom of your heel, with only a slight crease across the instep of your shoe.
• Shoes should be comfortable and in top notch condition, but athletic shoes should be worn exclusively for athletic activities.  Sad but true.  And just so that we are very clear . . . Walking from the car to a restaurant, movie theater or coffee store would not qualify as an "athletic activity".  Treat yourself, gentlemen, to some quality leather slip-ons or casual tie shoes.  It's amazing how soft and comfy good leather shoes can feel and even more amazing how good you can look wearing them.  
• Just in case you ever need to wear a tie,  it should be straight, not tight!  And shirt collars need to be sized for comfort around YOUR neck, not the neck of the guy in the catalog.  A word to the wise?  Don't assume you know your neck size. Try on a shirt before you buy.
• Jeans are great at any age but are appropriate only for very casual occasions.  Brands such as Wranglers, Levi's and even "nice jeans from Nordstrom's" do not belong in the office, no matter what your colleagues may say or do.  And jeans bought "off the rack" rarely fit well enough to be both good-looking and comfortable.  Please choose black [very sexy], white [perfect for summer], or dark wash navy blue denim rather than a faded stone-wash denim.  Make sure that they fit well in the waist and are plenty long, and then bring them to a tailor.  You can do this. 
• It's OK to wear sweats, sports T-shirts and sports jerseys when you are actually playing in a game, attending a game, on the couch watching a game, or going out to a sports bar for the game with the guys.  Never are they appropriate attire for shopping, dining or working in an office, even on casual Fridays.  It's just not right.  It's just not cool.  Period. 
• A jacket [sport coat/blazer] is a wardrobe staple that should be in every man's closet. [I am talking about a "blazer" jacket, not your official NFL  jacket or a leather bomber from  "back in the day".]  It camouflages extra pounds beautifully but if weight around the middle is not a problem for you, consider this: a blazer style jacket can also make one look taller and more "well built". [Now, do I have your attention?]  A perfectly tailored jacket with a crisp white shirt and casual slacks is appropriate and comfortable for the theater, a dinner with friends, and for just about any other occasion one can imagine.  I know it's risky to say this, but . . . one can wear a graphic or bright white T-shirt and jeans with a blazer and look casually fantastic.  You will need a very short, cropped haircut, a clean shaven face, leather shoes in good condition, and a bit of an "attitude" to pull off this look, but you can do it! [More mature men can look to aging rock star Sting for affirmation on this point.]  Yes indeed, gentlemen.  Invest in a high quality, great looking jacket and you are set.  Comfortable? Check.  Appropriate? Check.  Cool? Check and double check.  

Finally, please remember that a great body is never required.  If you can engineer a great fit, you will have both great comfort and great style.  Now, for the girls, "Let's give 'em something to talk about.  A little mystery to figure out". [Bonnie Raitt, singer-songwriter]