| When I was in college I developed a strategy that worked very well, in fact I was considered the best dressed man on campus and one girl even wrote a letter to the student newspaper (which was published) asking about me. My strategy was simple, affordable, and I built a solid and adaptable inventory of clothes that could be used for different types of styles. Here's what I did:
First, I went to the local shopping mall and looked at what all of the male mannequins were wearing. The mannequins will always be wearing the most up-to-date versions of what is considered fashionable. I rarely entered any of the stores, I only looked at the displays in the windows. Then I went directly to the three thrift stores in town and bought clothes that replicated the mannequin's look.
I shopped on Thursday because thrift stores are shopped hard on the weekend, but not the weekdays during which time they are restocked, so their inventory is at optimum levels on Thursday (or early Friday mornings but I had classes on that day). You'd be amazed at how much designer wear you can get at thrift stores for pennies on the dollar. I still shop that way, in fact a couple of months ago I got a Kenneth Cole peacoat and a Bill Blass winter jacket for $10 each, both still had their Macy's tag on them (they were never worn) and the former retailed for $285, the latter $250.
I also learned a few things about "dressing well":
1) Dress in layers. More color and more texture makes for a sophisticated look, even if it is casual. When you go to the shopping mall you'll notice that almost all of the mannequins are dressed in layers.
2) Use small details to your advantage. Add a bracelet or two, maybe a necklace. The same goes for a piercing and as a guitar player you could pull that look off. The small details help to define your look, and it's one of the many things on this list that the average chump doesn't do.
3) WOMEN NOTICE YOUR SHOES. They should always be clean and not shaggy or worn out. Do NOT wear sneakers unless it is a specific part of your look. Most guys wear sneakers, and you do not want to be most guys. Get a pair of Doc Martens or something like that - far better than sneakers, stylish, but not too dressy...plus they have a heel which will make you appear slightly taller. In fact, make a mental image of yourself just following the first three items here: you're wearing a hip T-shirt, a short necklace is around the neck and over the T-shirt, you've got a leather bracelet or watch with a leather strap, and a pair of Doc Martens on your feet. Isn't that already a major improvement style-wise? A good belt would help too, but it doesn't have to be too flashy. It does need to match the shoes (Black shoes, black belt. Brown shoes, brown belt).
4) Pick out your next day's clothes the night before. You'll do a hell of a lot better job of it then as compared to the morning when you're half-awake and rushing to get to work. People who pick out their clothes in the morning tend to fall into the same old habits, over and over again.
Budget $25-50 a week for clothes (thrift store T-shirts run about $4 a piece, jeans $7 where I live, even the designer brands) and go shopping once a week. Do this and I guarantee you not only will your style of dress improve, but you will begin to develop your own personal style along the way, and that's dressing becomes fun and not a chore, and it is also when women really start to notice.
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