Unconventional, Yet Practical Advice for Dressing Better
Some not so basic principles to better style.
Style is a journey. As cliche as it is, style, like many things in life, is going to be a lifelong journey that you’ll embark on. While there will be times that you look in your closet and think to yourself none of these pieces look good on me or I’m not good-looking enough to get this outfit off, you’ll also experience triumphant feats of nailing the perfect look and feeling comfortable in your skin. Style isn’t important to a lot of people, but personally, I find myself feeling my best when I’m wearing a good outfit (and exercising…eating good foods…etc..) and putting effort into my appearance.
There is a lot of cookie-cutter advice for dressing better - e.g. wear navy and brown together, find clothes that fit your proportions, but we’ve heard all of that before. There are a lot of unconventional ideas that I’ve implemented over the years to get to a place where I feel like I know my style and what looks best on me. These are pieces of advice that I feel aren’t as well-talked about when it comes to giving style advice, but it’s worked for me. Without further ado, let’s jump in:
Watch A Lot of Films
There are a lot of great films out there to get style inspiration from that are already well documented. Sure you can watch American Giggalo and start scouring eBay for all of the vintage Armani that you can find. You can watch The Talented Mr. Ripley and lean into the 1950s Mediterranean look of camp collars, knit polos, and traditional prep. A lot of style blogs and magazines have long posts dedicated to stylish movies, but there are many outside of those parameters that I’ve found to be inspirational to me. No one talks about the biker-chic or punk rock clubgoers in Scorsese’s underrated 1985 masterpiece After Hours or Humphrey Bogart’s dissolved tuxedo from In a Lonely Place.
I’m as much of a film lover as I am a fashion lover and I believe that indulging in great art makes us better people, so I try to watch as many movies as I can. I was watching Rainer Werner Fassbiner’s Ali: Fear Eats the Soul the other night and I loved the way Ali (portrayed by El Hedi ben Salem), a Moroccan immigrant, dressed throughout the film. He wore shirts with ties under a perfectly fitting blazer and blue bell-bottom pants with good boots for many scenes in the film. His t-shirts fit him perfectly, the sleeve sitting just above the bicep, when Ali is sitting around the house. The film will never end up on the list of most stylish cinemas, but I couldn’t help but take a few screenshots to revisit down the line to use as inspo.
Build a Collection of a Specific Accessory
This can be anything. Never underestimate the value of good accessories and their ability to on taking your outfits to the next level. Your thing can be jewelry related - rings, earrings, bracelets all make good accessories to collect. While I do consider myself a watch guy, the accessory that I consider myself a ruthless collector of is San Francisco related hats. I have a few Giants and Niners hats as well as hats from events like concerts and festivals, and the public transportation agencies just to name a few. I have complicated feelings about the city, but it is my home, and goddamnit I’m going to represent it.
You can create a similar collection. I also have a ton of vintage San Francisco t-shirts. You can choose to collect something as specific as vintage 1960’s dress watches, or as broad as gold jewelry. Just make it your own.
Building a collection make you an individual!!! It’s called personal style, not collective style.
For the fellas: study stylish women…And Vice-Versa
I think women in general dress better than men in the sense that there are more well-dressed women in the world than well-dressed men, which I feel is okay to say. Women have long cared about their appearance before men did. The best influencers are women because they do not approach fashion with the same mentality as some of the male influencers. Men are so quick to shit on things that they don’t like, instead own just saying it “isn’t for them.” Negativity sales in the influencer world. It’s not something that I am interested in.
Aside from influencers, I think that models and celebrities’ stress style looks are very chic. Rihanna, the Hadids, Greta Lee and so many others are laying the foundation right now, and we can all take some notes.
Take a break from TikTok/Influencers to Discover What You Actually Like
You may follow a few fashion TIkTokers, a dozen or so guys who have drip on IG. There’s a podcast or two that you look forward to to get through the workday. That’s all fine and dandy, but let’s be real, you’re being fed the same fashion advice from like 4 or 5 different avenues. The trends are trends. Timeless clothing will always be there, but at the end of the day, you have to go out there and wear the clothes yourself. I’m not saying you should never listen to a podcast or unfollow all your favorite menswear personalities, but maybe give it a rest for a while. If you’re serious about having a tremendous, head-turning personal style, you’ll need to stop dressing like the cookie-cutter version of what an influencer is trying to mold. A lot of times, influencers are trying to push their way of dressing on others. Not very original.
Likewise, maybe don’t read as many fashion editorials or magazines. It may be good for finding new deals and hot new items, but unless you want to look like every other subscriber, you can afford to skip some fashion news.
Expand Your Definition of What Makes a Style Icon
We’ve been looking at celebrities and models as beacons of style since the beginning of fashion. Before celebrities it was the aristocracy, and now it’s celebrities, Twitch streamers and professional athletes. Most of us aren’t celebrities and do not have celebrity money. The keeping up with the jones mentality is ruining Milennials or Gen-Z. We need new idols! You may have heard the term “swag grandpa” from that one TikToker who said that she wanted to see men dress like “swaggy grandpas” all 2024. She basically wanted us to wear older, more lived in clothes. She got slandered for her approach, but I think she’s on the nose. We don’t need as much new stuff. All of the hot clothing is already all around us.
Your dad may be fly. Your grandpa too. The older people you see in bingo halls and Chinatowns - they might have a little drip too. Inspo is EVERYWHERE, even in the most unsuspecting places. Take from everything and everywhere and put your spin on it. I used to think that one of my professors in undergrad was a terrific dresser. I loved the desert boots he’d wear with his chinos and Oxford shirts and a perfectly fitting
blazer. It inspired me to buy a pair of desert boots in a different color and I wore them throughout college. You just never know where you’ll find the drip.
Peace and Love