Fancy Overcoat 

• Elegant, masculine, and urban, these long coats are essential for the well-dressed man.
• Wool,  cashmere  and their blends keep you warm for years.
• Can be long or three-quarter length, like a Navy Peacoat.  Never get caught wearing a coat that is shorter than your suit jacket.

Down Parka 

• Hip and somewhat practical, puffy parkas envelop you with down feathers.
• Down jackets provide warmth and breathability. They should be paired with your casual wardrobe and boots--not with professional work clothes.
• North Face,  Patagonia and LL Bean coats are all popular brands.

Multi-Layer Gear 

• Ripstop on the outside and fleece on the inside. Feel free to zip off any part of the equation you don't want that day. Great for winter sports.
• Many of these jackets come with sleeveless shells or removable fleece vests that can be worn separately.
• Columbia  and EMS  make reputable products.

Raincoat 

• An extra flap across the shoulder blades acts to wick away rain.
• Usually rubber, plastic or other waterproof fabric. Many of these coats lack ventalation and get quite warm.

Trench Coat 

• Classic and perfected by Burberry,  this is the belted brother of the raincoat.
• Usually a cotton or wool fabric treated with a water-resistant chemical.

Poncho 

• Either a big piece of hooded plastic  or a carpet-like woven cover.  Only the former is waterproof.
• Save these for hiking trips and outdoor football games. They are not stylish.

Rain Shell 

• High-tech outdoors companies have perfected these light, ripstop, and waterproof jackets.
• Many versions have wicking abilities for running and/or hiking.

Leather 

• Whether bomber,  motorcycle,  suede  or trench-style,  these are the coolest jackets possible.
• Quality leather could cost you a couple hundred dollars (Kenneth Cole ) or even a couple thousand dollars if you buy an expensive designer (Armani ).
• Wear with jeans or casual trousers. Dress up the look with a turtleneck underneath the jacket.

Denim 

• Lightweight and long-lasting, these will only get more comfortable with time.
• The hippest cuts and washes will cost more and grow tired quickly--avoid them.
• Never, ever, wear with jeans. The denim tuxedo look is horrendous.
• Stick to brands you know: Levis,  Gap,  J.Crew  and buy a classic cut.
• Wear with khakis, corduroys and other weekend-casual gear.

Sport Coat 

• With corduroy,  wool,  khaki,  and linen  available, the fabric and cut will dictate how fancy this coat gets.
• Blazers (also known as sport coats) are often a more stylish alternative to denim and leather.
• Opt for a sport coat with two or three buttons (single breasted of course!). Jacket should fit close to the body but not too tight.
• Start with a navy sport coat.  Your next purchase should be a subtle print.

Windbreaker 

• Often windbreakers have the same ripstop nylon as in the technical multi-layer jacket, making them lightweight and wind resistant at the same time.
• Since these jackets take practically no space in your bag, they are great for travel--throw these on when it's just a tad chilly and then throw it in your bag later.
• Can be very stylish  or ugly,  depending on the designer.

Military-Style 

• Safari,  military surplus  and military-inspired  coats get you lots of buttons, pockets, and ties.
• Actual military clothing is intensely durable.
• Too many pockets can make you look cluttered and silly. Only wear safari jackets when actually on safari.
• Same goes for camouflage jackets --save them for hunting  or military exercises.

Photographer Vest 

• Pockets everywhere! For the man who needs more than his cargo pants can hold.
• Great for photographers and hikers. Not a great idea for anyone else.

Down Vest 

• Nice and warm, except for in the arm.
• Practical for mid-weather days when there's a nip in the air. Right, McFly?
• Not a great style for portly folks.

Sweater Vest 

• Will keep you warm without sacrificing formality.
• Preppier than a popped collar at a yacht club.
• A nice layering piece with a sport coat.