If you’re just getting to know me through the blog, you’d probably be surprised to find out that I went through a pretty serious wannabe-gangster aka “wankster” phase in early high school. It was the height of Eminem and 50 Cent’s popularity and I simply just couldn’t help myself from rocking baggy sweatpants, jerseys, bandanas, all of the essentials of that era’s MTV labeled “cool guy”.

Aside from the hilarious photos to look back on (which will remain STRICTLY private), the one thing I can be glad about from that chapter of my life is my affinity for the Timberland 6″ Classic Boot. When fall rolls around, it never becomes official for me until I can dust off my Timbs. You can’t deny, these boots have always had somewhat of a stigma around them thanks to being preferred by so many rappers and urban artists, but that’s only because they’re a damned attractive boot, people! They’re awesomely masculine in a way that’s totally constructible. Let me tell you my secret…

With a piece like this, I like to surround it with items that deny the stereotype. Essentially, I become a positive version of a walking contradiction. These fitted raw jeans and slim, lightweight sweater aren’t what you’d normally see paired with Timberlands and that’s on purpose. A basic outfit like this lets the boots speak for themselves. It’s showing that I appreciate classic items like these but don’t need to change everything about my style to make them work.

These rules apply to much more than just construction style boots, too. Anything that might not normally fit into what you’re accustomed to wearing, surround it with things that are normal to you and then let the new thing be a pop of difference. It could be a jacket, vest, statement piece of jewelry…whatever. Just don’t be afraid of trying something out that you’re attracted to simply because it doesn’t mesh well with what you’re already used to doing stylistically.

Take chances! Sometimes it pays off and you build a lifelong friendship with something like I have with my Timberlands (yeah, we’re besties…we text all the time, get over it).

Thanks for reading!

Stay smiling, my friends!

PYS

P.S. The sweater is from Michael Stars Man, if you’re into it. Click here to shop.