You may not want to be a peacock but you may not want to remain the guy in basketball shorts and a tee shirt, so what do you do? One of the biggest misconceptions about guys dressing well (ironically among guys that don't dress well) is that you have to go out looking for designer brands or wear tight-fitting clothes.
To be quite honest, its much easier for guys to dress well than for ladies. Think about it, when you walk into the men's section there aren't that many options to choose from; on the other hand, you'd better found a comfortable seat when walking through the women's section. Retailers make it easy, so let's make it easier on yourself.
Get your fit together
The one and only aspect of style that will make you the stud you're going to be. Even the cheapest thrift polo will look better than a Ralph Lauren polo if it fits like a glove. More details will be given on this later, but a good start for late summer is to make sure that your shirt sleeves fit halfway up your biceps and don't fit any lower than the bottom of your pant zipper.
The difference between a $100 dollar suit and a $1000 dollar suit is simply the fit. Forget the brand name or where you got it from, because no one cares (this is why they don't have logos). All that matters is the fit, which is why high fashion suits are more expensive because of their superb off-the-rack fit.
Don't go logo
We're not that much into rules, but its a good rule-of-thumb that 90-95% of your wardrobe should be logo-less. Don't be the walking billboard, bro. That 5-10 percent of your wardrobe that does have logos should at least be workout clothes.
Seeing guys go out and pay ridiculous amounts of money for branded clothing is frustrating because this is missing the bigger picture of the purpose of wearing clothing. If one wears clothing for superficial, status-reasons then more power to ya. If you're in the style game to look good, feel good, and impress yourself plus others around you then its time to lose the logos.
Be overdressed rather than under dressed
For your own sake, you don't have to wear a suit to class. Most guys think there are two occasions in this world, ones where you dress 'up' or you dress 'down'. What about the in-between? Throw a button down under your sweater, wear a smart pair of chinos (pants that aren't jeans) with your polo and penny loafers, and play the layer game like there's no tomorrow with flannels and cardigans.
Never underestimate the power of good casual pieces. Even a well fitting pair of sweatpants will do you more justice than an expensive pair of khakis.
The Golden Rule of Grooming
No one will listen to the man unless he's groomed well. Don't bother upgrading your wardrobe until you, yourself is in tact.
We saved the best for last because shoes make the man, its not just a figure of speech. Invest in three pairs of shoes: a quality dress shoe, a casual loafer for class, and a pair of sneakers for the most casual of casual occasions. The first things that people look at when you're dressed are your tie and your shoes. Why? Its sad to say, but they're the biggest "status" symbols in your outfit, so make sure they're worth looking at.