Dressing well for men, is far more about style than fashion. By this I mean a man who dresses according to their body type and skin complexion will always be better atired than one one slavishly follows the latest fashions without regard to whatever flaws and imperfections they highlight or conceal
Starting with the hardest, the shorter stout man.
The first thing is to wear clothes that actually fit. Trying to squeeze into one size two small which just highlights the girth, or wearing oversized pieces that end up looking like tents. Start by wearing something that is correctly sized. This may mean getting it made as finding these pieces off the rack is nigh on impossible. One of the classic faux pas is chunkier people wearing skintight jeans, which simply emphasize the stomach/hips region and make you look like an apple on a stick!
Suits
Style wise, stouter men need to follow a couple of basic rules and repeat them ad nauseam. Their suits should all be two button single breasted (This will be repeated often in this series as this is the most flattering style for most). If possible ticket pockets, preferably angled should be present on all suits, as this creates a tapered line from hip to waist giving the illusion that it narrows.
Also very important is to emphasize the shoulders to make them look as broad as possible to counteract the belly. Peaked lapels aid in this greatly as it makes the shoulder look far broader. Conversely avoid narrow lapels at all costs as they will appear to get lost and make the jacket look for bigger.
Fabrics.
Look towards darker colours with faint to mid vertical patterns. The vertical stripes will aid in adding length to the appearances and draw eyes away from width, however avoid extremely bold stripes as this emphasizes girth by drawing attention directly to the stripe. Darker colours are better, as they avoid attention, lighter colours attract it, emphasizing size.
Trousers, always try to wear flat trousers with a gradually tapered leg. The line of the trouser needs to add verticality and make the leg look longer then it is. Pleated trousers will add far too fabric through the legs and billow like a tent, also cuffs need to be avoided as the shorten the line of the trouser. Always wear a belt to ensure the trousers do not slide down and look oversized. the shirt must always stay tucked in as well again to keep looking as long as possible and nothing undoes that quicker than an untucked shirt. This is actually a rule for almost any shape, but is most important in this case.
In summary, the stouter man has the hardest job, but if they follow these simple rules they can look fantastic
Wear correctly fitted clothing
Emphasize shoulder breadth
Emphasize height and length
Simple and subtle vertical stripes, patterns and textures over lighter plainer cloths
Classic tailored trousers with no pleats or cuffs
Here are two images of Zach Galifianakis, who I do consider one of the best dressed stout men in Hollywood. One he gets everything right in the darker suit with 3″ lapels emphasizing shoulders and a slim tie to add length to his frame. The other he has opted for a less flattering pale blue suit, that seems to draw attention more to his size and detract from his look.