The ideas of “dressing well” and “personal style” are a bit paradoxal.  While dressing well is essentially looking good in clothes to other people, you have to understand what you really like and what works for you.  The best dressers are really in tune with their personal preferences, and can be honest enough with themselves to admit that not everything trending will look good on them.  That’s not to say you shouldn’t take risks - it just means the more in tune and honest you are with yourself, the more likely your risks will work out.  Before you start taking sartorial risks, though, it’s probably prudent to start with a firm understanding of the basics (fit, proportion, color/pattern matching, etc. - more on those subjects in subsequent posts).

At the end of the day, you need to dress for yourself, and not strictly for the approval of others.  You need to be comfortable in what you’re wearing, because no matter how spreezy you [think] are, there will ALWAYS be AT LEAST one person that will look at what you’re wearing and think it’s wack.  I remember as early as two years ago, Alan our Style Director was wearing sweatshirts with paint stains and holes in them, and this progressed into this this fall/winter season, when Al started to wear all sweats err’thang with a draping Harris Tweed coat.  Alan called it “cozy boy swag”, but in all honesty I thought he looked bummy.  His wife didn’t like it either.  Next thing you know, though, we see pics of Eugene Tong from Details magazine blowing up Tumblr rocking very similar fits, and getting mad love on the interwebs.  Turns out people other than me and Alan’s wife like the cozy boy swag look.  Now, the point of the story isn’t to insinuate Eugene swagger jacked Al.  Rather, it’s to show “haters gon’ hate” (in this case I was the hater), so you have to dress for yourself and, as we often say at TCR, “do what you do young playa.”  

Personal style is really figuring out what you like and how it fits within the context of what’s relevant today.  If you don’t understand what you like, you’ll be easily swayed by the opinions of others.  You should also know WHY you like certain things, otherwise you’ll fall victim to trends.  Do you roll your pants ups because you like the way it makes the taper of your jeans look and/or how it subtly shows off your socks, or do you do it because you saw it on Tumblr and Instagram?  Do slim jeans work for you, or are you buying them because they’re “in”, and the tighter the fit the better the fades?  You get the idea.

Style is subjective, but above all else it should communicate who you are as a person and how you want to be perceived by the public.  As you become more aware of what you like, who you are, and how you want to be perceived, the more effectively you will be able to communicate these things through how you dress.