You see them everyday. In your office, on the subway, and at the grocery store. They are the evil that plagues many men and infects our retail stores. They are pleated front pants (especially Dockers), and they are usually some shade of khaki, although occasionally a brave guy will try a black pair. Now, these pants are touted as "safe" meaning they are appropriate for almost all occasions, so most guys buy simply because they are clueless. But really, no one looks their best in these pants, particularly if they don't fit properly, despite what a sizable group of men believes.
The Dockers issue isn't the only major faux pas seen on the streets. However, many common male mistakes are related. Number one: Guys, buy clothes that fit. Now, we're not talking skin-tight body builder lycra here, but properly fitted clothing will add some flattering definition. And women love it - how many (non -rapper) sex symbols have worn baggy clothing? There is an easy fix here, though. A great casual blazer (in leather, suede, corduroy, etc.) and some flat-front pants will take you anywhere. If you don't know which size or style fits your body best, ask the salespeople. It's what they are there for.
This rule is also good to follow when selecting shirts, whether they are button-downs or tees. The layered look is great, especially in the winter - try an oxford under a v-neck sweater (or vest) under a tailored blazer.
Now for the accessories. Although a guy's choices tend to be pretty limited, accessories are still a great way of adding personality and individuality to your outfits. Let's start with the shoes. There are so many sophisticated alternatives to sneakers available now that you have no excuse for wearing beat-up trainers with everything. Try some sleek slip-on leather loafers or, if you're a little braver, a pair of Chelsea boots. Heavier lace-up boots, done in a more refined fashion than your typical workboots, can add a funky touch to your 9-5 suits.
Your watch, cufflinks, and other jewelry is also critical when it comes to expressing your personal style. They should be made of the same metal (no mixing gold with silver here) and avoid anything too dainty. Never underestimate the importance of accessories - cool cufflinks are okay even in the strictest corporate environments.
Ties and silk handkerchiefs (the squares that you tuck into your breast pocket) are another area where all guys are free to express themselves. Note: this does not mean you should go out and get a tie shaped like a trout if you like fishing - you are a grown-up. However, you can and should go for bright, rich colors or intricate patterns. Do make sure that if you are wearing a tie and pocket square at the same time they are well-coordinated (one patterned and one solid, for instance) but not too matchy. Finally, always pick shades that flatter you, because it never hurts to look great.