Originally Posted by
PiCcolocV 
I would encourage you to be more thoughtful about this before choosing your style, and don't do what the majority of people who first come to this site do, which is blow a ton of money re-outfitting their wardrobe with new items based on images they see here or in magazines, then realize a year later "oh god, why?"
From a general approach to your dress, I get the sense you are not giving this the methodology it deserves (yes, I know you are 18, but that is no excuse to be dumb about getting into clothing - listen up and read all of this). While I don't agree with his style necessary, I do believe with this approach, and this is a great framework for you to start deciding which direction to go:
http://www.kinowear.com/blog/science-of-style-stage-1
In particular this part of the first section:
"
Stage 1 is a very important foundation to building your unique sense of style. Skipping this first stage is the root cause of many common image mistakes such as being incongruent with your personality, looking try-hard, or merely following trends that come and go."
I wanted to highlight that last part, because that is exactly what you are going to look like based upon everything you have said so far, and the pictures you have shown and magazines you like to draw inspiration from. People linked to some
seriously content and information-heavy threads around this forum earlier in this thread, did you actually go through and read all the comments and then cross-check the comments back against the original outfit? You will find yourself seeing a fit, saying "wow, I LOVE that - perfect!", then later someone points out problems like collar gaps, too skinny lapels, etc., and when you go back you wonder how you ever liked it in the first place.
Do you have a binder of cut-outs/print-outs of outfits you like (no, browsing images on the internet casually does not count)? Before you go out and spend all this money, have you actually taken the time to be familiar with many of the terms you will need to know to make smart decisions? Frankly, your approach is what commission-driven sales people in department stores drool over - some young kid comes in fresh off reading GQ, and wants a tailored but yet SW&D approach and suddenly you are buying a suit, pair of sneakers, and "who needs socks, in GQ they don't wear them!"
Speaking of spending money, let's talk logistics. Regardless of what direction you go in, clothing needs to fit you. This requires knowing your basic measurements, which brands fit you better than others, actually trying on tons of stuff before committing to buying, etc. Your case is tougher though, as having enough components to rock both the "prep" AND the SW&D look means you basically need twice the amount of clothing. I will tell you from experience, I have a decent job and spend a lot on clothes, and it is hard for me to even begin to complete my basic casual wear looks. God help you if you live in a place with 4 seasons, and need prep and streetwear for all of those variations as well. What exactly is your budget at 18 to wear well fitting clothes in 2 incongruent styles depending on what day it is or whether you are going out? More importantly, what are you going to do in 3-4 years when you suddenly need clothes for stuff like office work, and all of your "trendy in 2012/2013" is now being called out-dated and "yesterday" by GQ and they are instead pushing people to buy god knows whatever way the fashion pendulum swings next?
Were you planning on making a prioritized list of what items you would buy and in what order, starting with the highest priority? And more importantly, sticking to that list no matter how great a deal you happen upon at the mall? (pro-tip, malls never have good deals for the most part - compared to what this forum considers a "deal" anyways). Don't waste your money, you found this place and you asked questions - that is a good start. Spend another 6 months feeling everything out and getting up to speed on knowledge, you have plenty of time to buy and wear clothes at your age. Based on what you have posted so far, my guess is the conclusion you will come to is your top needs are a basic pair of well fitting, dark jeans like this:
along with a button down shirt, some polo shirts, decent pair of brown shoes, and maybe even your first legitimate blazer, etc. Fill in the gaps in order of the things you will get the most utility out of. For me, it is far and away my jeans which when seeking them out I intentionally sought ones that ended up fitting like the above. Keep in mind how versatile something like that is, compared to ultra-skinny jeans or baggier, raw denim with rolled cuffs - stuff like that can pull double duty of blazer and or polo shirt, or even something more streetwear.
Let's be real though, sure it is not impossible to wear sneakers with a suit and no socks and look good, I have on occassion seen it done on the SWD thread here. But these are people with MUCH more knowledge, and frankly probably a much, much larger clothing budget, than you possess.
You, being 18 and with what I imagine is a limited budget and prioritizing "looks" over "fits" - you will look like an absolute try-hard tool, that no one thinks dresses well, broke having spent all their money on shit that will be falling apart and out of style in 4 years.
