“Do my Timberland boots make me look hip-hop?”

As my friend Ben O. likes to say, “Here’s one for ya.”

Are racial connotations (real or imagined) a reason to wear or not wear a clothing item?

The reason I ask is because I was confronted with this question last night after I got home from the mall. I was checking my email and an IM friend I have messaged me, telling me about his new Timberland PRO Boots. Timberland PRO is a series of boots designed for construction, and while they leave something to be desired aesthetically in my opinion, they are decent boots overall.

My friend already owned a pair of the premium Timberland boots, as do I. But because of Timberland’s popularity with the “hip-hop” set, my friend was squeamish about wearing them. In fact, the way we first met was that he emailed me asking if “regular guys” still wore Timbs. Why this is an issue escapes me, but that’s what he said. I tried to allay his fears and explain to him the while a lot of hip-hoppers wear Timbs, it’s not really a “hip hop shoe.” In fact, after several years of frequent wear, Timbs are becoming passé in hip-hop circles. I thought that was the end of it.

As we began to IM over the past couple months, the subject of the Timberlands came up at least once a week. I kept telling him that the shoes were not hip-hop, but he never believed me. He sent me pictures of him wearing the shoes, and I told him again and again that they looked fine, but he never believed me. It continued to bother him.

He then tried a new tactic. He began sending me pictures of boots that weren’t Timberlands but looked a lot like them for my approval. This went on for several days, and I told him that there was no need of buying boots that looked pretty much identical to what he had simply to get something that was not Timberland.

The last tactic he used was posting his query on message boards I frequent looking for yet more answers to this question, which had become an apparent issue for him. Most people who responded told him the same thing I did.

This brings us back to last night when he was telling me about the new boots he bought, and that he was getting rid of the other, presumably "more ghetto" boots. I got concerned (but not upset) and expressed those concerns to him. My primary concern was that he was telling me (as a black person) that he didn’t want a shoe that was connected to a mostly-black cultural movement. My secondary concern was that even though I tried to steer my friend in the right direction, he obviously did not trust me.

We both walked away from that conversation with some mixed emotions.

I’m curious about what other people think of this. Should the boots (or any clothing for that matter) be an issue if you personally like the clothing? Is this something that other people struggle with? Should I be offended that my friend doesn’t trust my opinion or want to be associated with hip-hop?

I just don’t know what to think, and anything you can add or offer would be appreciated.