“Where it all started…” (My Style Manifesto Pt. 1)
As a youngster, I never considered my dad to be super stylish. He usually wore a suit to work, but nothing extra fancy. Because of this, I rarely noticed all the clothes in his closet that he never wore. However, by the time I finished college I started to dig into his closet more often. A lot more often. I realized he had a perfectly maintained retro wardrobe that I immediately started to plunder at will…jackets, ties, pants, etc. We were about the same size so everything fit just about right, with a few exceptions. That was the moment when I started to realize the early elements of my personal style: mixing new and classic pieces as well as throwing in some unexpected combinations here and there. I would wear ties with Timberlands, vintage T-Shirts and blazers with crispy AF1s, or a fedora and some wristbands here and there…very few hard and fast rules, just whatever felt right and looked good.
Fast forward. As I contemplate it now, having “style” is about doing something that’s unexpected but doesn’t offend your sensibilities of good taste; wearing items that you can wear confidently and comfortably; being distinctive without being too showy. Plus, it’s important to be able to switch it up and have a good working range of items to mix/match depending on the occasion, time of day, and season. I’ve been fortunate enough to surround myself with a lot of artistic folks, so I always find inspiration in what they’re working on and sometimes that reflects itself in my personal clothing trends. By the way, I rarely ever say I wear “outfits”; I always say I wear “pieces” because I usually envision wearing a particular item with many others in my closet.
Beyond amassing pieces, the trick is how you throw everything together. At this point I’ll be blunt and let you know I give zero advice on putting pieces together, save for one important tenet: keep it comfortable. It doesn’t matter how dashing or unique your clothing choice is; if you’re uncomfortable you won’t wear it right. It’s that simple. I also don’t normally focus on the technical aspects of fashion outside of knowing your true measurements to make sure everything fits appropriately. I just really like to stay focused on what looks good, what feels good, and how well it fits.
BTW, here’s a graphic on knowing a “good fit” when you see it.
Unfortunately for a lot of guys, we don’t have consistent style role models who we get to see in a variety of settings. Most of your best-dressed folks (in business or otherwise) are public figures who usually have a team of folks helping them with everything from personal shopping to designing specific looks based on the occasion. Ironically, in hip-hop you usually see a transformation in an artist’s wardrobe as he becomes more successful, gets more involved in business dealings, and starts to travel more (overseas touring or just for vacation). That last point just might the most important: One of the best ways to develop a varied fashion sense is to travel more (or at least watch more foreign programming); by doing so you’ll get a feel for how trends move, what you can “borrow” for your own wardrobe, and which places have the best options to find what you like to wear.
Lastly, don’t be afraid to take cues and compliments from women. In case you haven’t noticed, stylish women usually like to shop and they can often tell you about stores that have things you might like. Plus, if you find shopping laborious (like me), bringing a woman along who digs your style is often a great help and a cool way to get some feedback on the process. And if you’re in a relationship, that also helps her take the guesswork out of what clothing pieces to buy for you and how they’ll fit.
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