Height is always associated with body type.
This is true with off-the-rack menswear.
Clothes for very tall men are almost always baggy and broad.
Clothes for the shortest end of the rack tend to be tightly-fitted and boyish.
In either case, there is usually little variety, which makes for a frustrating shopping experience.
Men built both short and wide should take heart — some of the best-dressed men in history were built both short and stocky.
The iconic Duke of Windsor was only about 5'6″ tall, and Winston Churchill around the same; both helped to define menswear as we know it today.
Neither one was particularly boyish or waifish in frame, particularly in their later years!
Both men took full advantage of bespoke tailoring, of course (as any man with the available resources ought), which eliminated the dicey problem of fit.
But even a man buying off-the-rack can outfit himself reasonably well if he shops for specific visual elements and clothing styles, rather than trusting to the items a store manager has labeled as “short” or “wide” or any other number of largely meaningless categories.
1. Good Looks For Short Men
Conventional wisdom holds that shorter men all want to look bigger, and the result of that glaring generalization is a lot of chunky, padded clothing with vivid vertical striping.
And there's nothing wrong with either of those, inherently, but they're not taking the full picture of a man's body into account.
Any man's clothing should ideally draw the viewer's attention up toward the face, and a shorter man particularly wants that journey to be smooth and unbroken, giving the impression of height without striving to add it.
Vertical elements and smooth, unbroken surfaces are friends to the short and stout. The popular vertical stripes may be all right in moderation, but like all patterns they tend to catch the eye and look odd when they bend over the shape of a body, particularly a wide one.
Plain, dark colors should dominate the outfit for the best possible look. Simplicity is the key to the well-dressed stocky man, so try to avoid lots of layering and visual clutter.
2. Trousers For Stocky Men
A longer lower body give the impression of a taller man, so pants should be worn high. This is particularly flattering for men with a wider waist — the front of the trousers can drape smoothly over the lower stomach, rather than needing to be tightly belted beneath it.
Suspenders will help make a particularly clean drape, and eliminates the line of a belt cutting your height in half as well.
Men with broader waists also benefit from pleated trousers rather than plain-front. Pleated trousers do tend to be cuffed, however, which shortens the appearance of your legs somewhat; most tailors will be able to turn some of the cuff under to narrow it down and reduce its visual impact.
Dark-colored trousers will also hide detailing like cuffs and pleats better, making for an overall smoother appearance than khakis or light-colored jeans.
3. Stocky Men's Shirts
There's no specific measurement that determines the perfect shirt fit, but there is a distinctive look:
Long enough to tuck in, loose enough not to stretch tight against your skin when you do, and fitted enough that there isn't a billowing or “ballooning” of cloth around the trouser waist.
Shirts made from thicker or stiffer cloths can be worn more closely-fitted, since they resist stretching and taking on the shape of the body underneath them.
Dark colors continue to serve a broad man well here, and they hide the undershirt better if one is worn as well.
Solid colors will be more flattering than patterns overall; stocky men who feel the need to indulge in patterns can opt for very narrow, widely-spaced vertical stripes of a light color against a dark background.
Ties, if worn, should be long enough to reach just past the trouser waist, and should not be excessively broad or flat-tipped.
4. Jackets On A Short, Stout Man
A sport coat or suit jacket is almost always a flattering effect for a heavyset man.
The silhouette of the modern American suit coat is modestly squared at the top, tapers inward, and flares a bit at the bottom, creating a very slight “hourglass” with a distinct slimming effect.
A single-breasted jacket with a low button flatters broad men the most, and the long “V” shape of the shirt front adds an impression of height as well — but be sure the coat can button without straining.
There's no need for excess detailing (it just keeps the viewer's eye below your neck), so look for simple, solid-colored jackets with two slanted pockets at most.
Some casual jackets have no exterior pockets at all, which in a dark color is extremely flattering to a broad man.
Peaked lapels can add a dashing touch that helps move the viewer's eye upward, but avoid any that flare too far to the side — an overall upward impression is still the goal; too much of a broad, sideways sweep will make you look wider than you are.
5. Off-The-List: What Short & Stocky Men Can't Wear
Don't panic. It's not actually a very long list. Stoutly-built men just need to avoid anything that adds bulky layers of cloth or strong horizontal patterning — checks, grids, and so forth are right out.
Double-breasted suits are also less than ideal, since they add a heavy layer of cloth over the chest and shorten the upwards-pointing shape of the shirt beneath the jacket. Light colors aren't strictly forbidden but are probably less flattering than darker options.
Outside of those barriers, there's a world of possibilities for well-dressed men built shorter and broader than the average — though it may take a tailor or a lot of shopping hours to find the needed garments.