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6. Read this forum a lot, but don't let it influence you too much. Develop your own sense of style relative to your age. Don't forget that most of the people who will post here are much older than you and, therefore, dress older. You don't need that.
It will be too difficult to maintain your allegiance with your hoodie wearing self once you take the advice from here. Seriously if you do wear penny loafers, there is really no way to say you are going to delicately and strategically transition yourself from that style to that style. Most people will laugh at you whether you know it or not for wearing penny loafers if all you have ever worn were tennis shoes. My advice will go against the few you have gotten: splurge and take on the prep look without apologies. (if you can afford it). checkout this site if you have no clue what prep means www.prepidemic.com. My strategic advice if you can't afford a full on splurge: buy and stock up little by little (this may take a while) and when you are ready BAAM! The new you will come out.
Am I the only one who thinks preps look like douche bags? BTW, unless you actually grew up in a preppy environment and picked up the style there, you won't pull it off anyway. Everyone will see you for the wannabe you are.
It will be too difficult to maintain your allegiance with your hoodie wearing self once you take the advice from here. Seriously if you do wear penny loafers, there is really no way to say you are going to delicately and strategically transition yourself from that style to that style. Most people will laugh at you whether you know it or not for wearing penny loafers if all you have ever worn were tennis shoes.
Yes. It's a fine line, picking clothes that fancy but age appropriate. I think this provides a good template: