Gentlemen, I want you to do something for me. I know it is tough, even painful, but from the truth we can begin to make progress. Stand in front of the mirror and do an objective assessment. You needn't obsess over your every stray hair or perceived flaw, just become aware of your overall material. Face what you are presenting to the world. Ask yourself some hard questions about your choices in areas other than your clothing. Is your hair cut or styled in a manner which fits your standing, your objectives, your sense of who you are? Is your facial hair working in your favor or is it a distraction? Nails trimmed? Basic hygiene?

There may be drastic decisions required here. People tend to hold on to a look from a time when they were comfortable. They also tend to fall into patterns of safety and comfort. You need to look at yourself as with new eyes and make a fresh, conscious decision whether to keep each part of your appearance or to make a change. A lot of makeover shows like to go for the drastic change. That isn't necessary. Say you grew your hair out back when it was cool and it remains long. If it is luxurious, you don't mind the care involved, and you can style it in a reasonable fashion, don't feel you need to have it hacked off under the jaw. If your hair is one of your trademarks, make other changes. But if your hair is overgrown, stringy, is always in the way of what you are trying to do, why not consider a cut?

Work your attributes. That's your goal. Make note: were you blessed with muscular calves? Many men, no matter how unflattering their midsections, have excellent legs. Shorts aren't acceptable in every environment, but there are many places where they are the best choice. You could begin to find yourself more and more in such places and situations. Pair your shorts with a sweatshirt or a tee (sleeveless, if you dare) for outdoors. Pair a more structured short with a button down or one of the pairings I'll list below and you can work casually, run errands, or hang out in style and ease while letting your assets show.

If you don't have calves, you have Something. Find out what that something is. If you can't see it in yourself, ask a friend. Ask a stranger. You never have to see that person again.

Once you have a base from which to improve your presentation of self, you can begin to look at how clothing choices can add a positive effect to that presentation. If you are a man with a little extra heft, there are ways in which your clothing can help you to achieve a more slimming silhouette.

Layers

Who needs to tuck? It looks dated, uncomfortable. While you don't have to appear wrinkled and grunge, you can simply forgo the instinct to be beholden to the old rules of fashion. Free your shirttails! Firstly, comfort in your clothes will be evident in your carriage and posture, your attitude. Secondly, you lose that extra around the middle that, let's face it, immediately begins to form whenever you move and clothing shifts and bunches. You don't need the hassle or the appearance of added pounds. Let the drape of your shirt, even a simple tee, hide that bit of belly. For a little extra help, layer a couple of loose-fitting shirts: pair a sweatshirt and a tee, a 3/4 length sleeve with a tee over the top, a plain or even dark colored tee or pullover with a buttons open buttondown. If your arms are more toned, add a rakish roll to the sleeve. Let the loose fit style work for you. If you are indeed blessed with decent arms, a baggy pant and a dark, loose tee may be all you need.

Bulky items

Especially in colder climates, our bodies don't want to let go of those additional calories and since time began we have had the perfect solution: sweaters. They are not interchangeable. If you choose a fitted cashmere item this won't provide you much disguise. But sweaters come in a wide variety of knits and patterns and material. There are turtlenecks for those with issues which extend beyond the collar. With a sturdy cable knit it isn't possible to tell if the bulk comes from your frame or the garment. A fisherman's sweater can lend an air of the outdoorsman, even if you've never been out of the wilds of your own yard. This may be one area where your playful side can emerge without too much damage to your overall look should you enjoy a more ostentatious display; however, stay away from holiday patterns and decoration.

Color

We each have a distinct personality. And there are reasons based in our genetic history why we may be drawn to the use of color. Please consider, though, that color will draw as much, if not more, attention than fit when it comes to your wardrobe. You needn't abandon your whimsical side, simply become aware of what you're wearing and where it encourages the eye to slide. When paired with a more muted or darkened choice, color can be your friend. Use its attraction to focus attention away from your problem areas. At the same time, you could use color as a part of your own personal signature style. Perhaps you have a fondness for shoes? A wild colored sneaker. Ties now come in fantastic prints with delicious graphics. A certain kind of man can even rock a scarf. Awaken your creativity.

Tailoring

Almost any choice in clothing can be enhanced with a proper fit. A decent tailor can use his/her skills to bring an old garment into fashion again, make a piece you enjoy better behave around your particular shape, or use his/her work to help smooth over your rougher areas, directing attention elsewhere or at least mitigating the damage they may be doing to your overall presentation of yourself. A great improvement in your image may be only a fitting away. You might be surprised to find that when your clothing hangs better, when your clothes sit on your body as they were meant to do, what an extreme visual difference this can make. Maybe your waist isn't quite where you thought it was...

The Suit

If you have the ability support a more formal lifestyle, the suit can be your greatest clothing ally. A step beyond camouflage for flaws, the suit draws attention by enhancing positive attributes of the male form and allowing the eye to skim over the rest. Broad shoulders are created or accentuated. The waist can be completely disguised or give allusion to a taper. The waistline is obscured and most of the body is covered, giving the benefits of most if not all of the ideas mentioned above: layers, draping, tailoring, color, style.

Ethnic clothing

This is not for everyone. Consider this the Surgeon General's warning of clothing choice. But if you are a person with the right or background to make an ethnic clothing choice, not someone trying to pass as something you are not, there are exceptional alternatives to be found in this area. Whether the simple, beautiful uniform of a martial art or the elaborate embroidery and pattern of a foreign culture, there are tunics, robes, manners of draping, which make the figure beneath a mystery or a non-starter. Beware: You want to avoid the appearance of a costume.

Subculture

There are groups and gatherings where costumes are a requirement. A person of size can rock a cape, can own a wizard's robe. While you won't be wearing this to the mall (please, I'm begging you), there are historical re-creation societies, gaming groups, where you can dress outlandishly and be in good company. A local theater group may be the place where you feel at home and you can find almost unlimited options for mixing it up within your wardrobe while covering up a part of you that displeases. Think of those loose-fitting shirts of the swashbuckler, the rakish dip of their sabre belt...

The Trenchcoat

A quality trench, left draped open or cinched at the waist, can, much like a suit, lend instant style points and credibility to the wearer regardless of size or overall shape. They come in a variety of colors, but the traditional khaki shades should work for anyone.

The Hat

Once was a time a man wasn't complete without his hat. Younger people may be limited in their exposure to the older, more sophisticated styles which once ruled. A bowler/derby, fedora, even a cowboy hat, can lend a certain air, a credence, to a man. There are subtle, symbolic, nonverbal cues involved and one shouldn't choose a hat lightly. Definitely search out a hat that fits who you are as well as it fits your head size. In a way, you wear the hat and the hat also wears you. Again, you want to avoid the appearance of costume; irony is fine, being a joke is not.

Jewelry

Here I want to speak of two types in particular- the watch and the necklace. Men are blessed with the ability to wear larger, chunky pieces that most women could not pull off effectively. For the same reason, a larger man can more easily wear a flashier piece than could a smaller or more slight man. A respected brand of eye-catching watch worn at the wrist draws the eye away from the midsection. It can also become a converastion piece. The same goes for a necklace. Think of an American Indian, the heavy silver and turquiose ornaments, the sheer size of a medicine pouch- and yet these do not look out of place. You want to choose an item which fits your life, says something about you. It doesn't have to be a purely masculine item. Surfers enjoy wearing shell necklaces, for example. The colors and shells themselves may at first seem feminine in nature, but in context with surfer culture, they are perfectly harmonious. Take your time and pick a piece which similarly represents you.

Above all, you should dress in a manner which makes you feel happy and positive. This feeling will radiate out from you to affect those around you. Your confidence and positive feelings will cause you to hold yourself more upright, introduce ease into your movements, lighten your mood and enhance your personality. All of this will add to your attractiveness and self-esteem, which again make you feel more confident, in a wonderful circle of effect.