Style Advice: A Guide to Finding Your Personal Style

  • 9 min read

How to find your own style

With age comes experience, and with experience comes style - eventually you settle in to knowing who you are and how to best present yourself to the world around you.

It should be obvious, but I will note it anyway - only YOU can find your own style. The goal of this article is to pass some experience your way, in how to go about finding it.

In addition to my own thoughts, I’ve asked some of the most stylish people I know for some tips. We’ll cover a few categories, including grooming, how to find the right hairstyle, and how to dress yourself.

stylish people who helped with this article

Section 1: Variations on Grooming

Key to grooming is that your grooming style should fit your lifestyle.

For example, to shave or not to shave? 

I’ve had a beard for 10 years - I used to shave daily, but eventually I realized I preferred having facial hair to spending 10 minutes shaving every morning. I know many people who enjoy the ritual of shaving, and if it’s something you don’t mind doing, that could be reason enough to keep a clean shave.

There is perhaps no higher authority on beard grooming than Ouigi Theodore (pronounced “wee-gee”), owner of the Brooklyn Circus, who was once known familiarly as “the Bearded Man”. Ouigi says, “My grooming style is always an evolution of how I feel and where I am in life. Since I cut my long beard and retired ‘The Bearded Man’, my approach now is to keep a permanent 5 o’clock shadow and let my grays shine. It looks neat, approachable and yet a bit casual. It’s my ‘tailored casual’ vibe.” 

Noting that his grooming revolves around his schedule, he says “with my hair, I’ve gone from a higher Caesar, to a wild ‘fro, to now a more manageable, but low Afro. No fade, and no taper. I am too busy and travel too much to upkeep anything that is too manicured.”

Ouigi Theodore, Brooklyn Circus
Ouigi Theodore, Brooklyn Circus founder

I asked Nico Colón, gallery owner and artist, why he keeps up a shaved look: 

“I shave with a straight razor, you can get a much closer shave that way. It's subtle, but (having a shaved face) looks more sophisticated and adult to me. I like to think that we can look better and better with age. This is part of that.”

Offering more insight into his routine, Nico says, “After I shower I use oil on my face, everyday. And I hydrate. Also, running everyday keeps me feeling good which can only help in how I present myself.” 

Nico says his biggest fashion influence is his father, “He is from New York, Puerto Rican from Manhattan, and always dressed well. A little flashy even. But he taught me that it was important to look good and take pride in how you look.”

Nico Colon at his SF gallery, Climate Control

Beyond the beard or close shave, another option, is the mustache. Garrett Munce, writer and grooming editor for Men’s Health, Esquire and more, is one person who really pulls off a great 'stache. 

I asked him how that came to be: “I was always a clean shave type of guy. A couple of years ago I decided to give the mustache thing a try out of curiosity and I realized I really like it." 

Key to a great mustache, beyond thickness, is owning the look and making it a part of your personal style. That's why it works for Garrett, who says, "Now I feel like it's part of my look. I'm really embracing my Daddy era.”

Garrett Munce, Grooming Editor for Men
Garrett Munce, Grooming Editor for Men's Health and Esquire

Garrett’s a well documented groomer, famous for his“Facial Fridays”, and he shared his favorite ritual with us, which he calls the Everything Shower, "Once a week, I do a long shower where I do things like scalp scrubs, body exfoliation, face masks, body serums/lotions/oils and just really work everything head to toe. it takes a while, but what else am I going to do on a Sunday evening? I like to take my time and really enjoy it.” 

Grooming Summary: 

Priorities are a major driver of grooming style. Figuring out how much time you want to dedicate to grooming is a great start. If you're into it, you might enjoy a shave or a more unique style, like a mustache. If you don't want to dedicate consistent time to grooming, keeping some form of a beard is a great way to give yourself back some time. 

Section 2: Finding a Hairstyle that Suits You

Whether you buzz your head, grow it long, or something in between, the goal should be to find a look that suits you best.

My personal hair journey has gone through many stages. In grade school I started with the hairspray stage, creating a rock hard hairstyle that wouldn’t move, even in a windstorm. I remember loving the crunchy feel. I soon learned that no girl, no partner, likes that crunchy feel :). From there, I jumped to a very natural look, which I would now call a “curtain cut”. I started getting a fade in middle school, and eventually that lead to a shaved head period. I gave myself a faux hawk for about a year, and those old pictures are somewhat regrettable :). Today I'm back to a more natural look, still shorter on the sides but not to skin, embracing the grays. 

My haircut and hairstyle advice is to find a style that fits your face, something manageable to your lifestyle, and to use natural styling products which showcase who you are, versus synthetic, unnatural products which make you look like you’re trying too hard.

Evolution of grooming
Years: 1989 - 2019. Who would've thought this kid would start a pomade company :)

How to find a hairstyle that suits your face?

I asked Brandon Faulk, very talented member of the crew at Church Barber, and he offered the following tips for how to find the right hairstyle: 

"I always recommend that people go for a look that is the opposite of their face shape.

For example, if you have a square face, go for a softer and rounded shape. 

If you have a round face, go strong and square shaped. 

If you have a wide face, go tight to the skin which helps make the face look less wide. 

For a longer face, I’d suggest a forward style like a crop/fringe cut, or something with low volume like a curtain cut, which will prevent extending the already longer face.” 

Brandon Faulk Church Barber
Brandon Faulk, Church Barber

Note: If you don’t have hair or are losing hair, you’re in luck - buzz cuts are always in style.

One very cool and stylish person I know who's always kept a shaved head, is Calvin Leung, currently creative director at Gap. 

“When I was 14 I tried to give myself a fade and I went way too high. So I decided to shave it off. From there I never went back.” 

Of his routine, he says, “Since I shave both my head and my face I do have quite the routine. I trim my face about once a week depending if I need to look presentable or not. For my head I shave as needed. I use a shaving serum and a razor then a post-shave lotion. I then finish off with a vitamin C serum and add a light sunscreen for the day, or a moisturizer at night.”

Calvin Leung on a PJ

Hairstyle summary: 

If it fits your personal style and face, and you love barber shops, getting a bi-weekly fade is a nice ritual. Conversely, if you dread a trip to the shop, you need to find a great barber or stylist who can cut your hair in a way that grows in well over a long period of time. In either scenario, nothing will ruin a good hair cut more than cheap styling products that make your hair untouchable, and worse, could compromise your hair and scalp health. So opt for natural. And if you're losing hair, or don't want a high-maintenance cut, you should shave your head - it's a great look when you embrace it and work it into the rest of your style thoughtfully. 

Section 3: Personal Style and How to Dress

Over 42 years, I’ve spent hours looking at clothing in-person and online. This window shopping habit and obsession with clothes has led me to spending a fortune on clothing - so I think I’m well positioned to say, money cannot buy style. If I had a dollar for every item of clothing I’ve spent an embarrassing amount of money on to then wear only one or two times, I’d be rich (only after subtracting the stupid amount of money the clothes cost me of course).

To that point, I’ve found there are three core types of people, when it comes to style and fashion - people who enjoy watching trends and riding the style wave, those who care how they present themselves but value ease of life more than style, and people who could care less.

If you’re in the first camp - “style surfers”- you’ll learn over time whether you’re a big wave rider (someone who can pull off being fully on trend), or more of a boogie boarder (someone who “gets it”, but doesn’t over do it). The sooner you realize which waves you can handle, the better.

Church Barber regular and stylist David Rojo, from our neighboring store MAC, is a very high-fashion guy who pulls it off with ease. He’s someone I would classify as a “big wave rider”, and he says, “I used to dress in more conservative, traditional, and buttoned-up menswear looks. Now it’s come to the point where I feel more free than ever to take risks and push the envelope. I think it’s a function of growing older and feeling more and more in touch with who I am.”

I asked him for his advice, on how to find your style and he says, “Start out by wearing what makes you feel like the best version of yourself, that’s the point where you start deriving power from your clothes. And then don’t be afraid to start experimenting and playing around a little after you arrive at that baseline. That’s how I think you refine and evolve your personal style over time. It’s a measured thing, definitely not going to happen overnight. But at some point you’re going to start having fun getting dressed, and that’s how you know you’re doing something right.”

David Rojo at Church Barber

If you’re someone who’s in the middle (doesn’t follow trends), or someone who doesn’t care at all what you wear because you’re more concerned with “real life” or whatever you’d call it - I think you’re in luck, especially if you’re reading this. Your only job now, is to find one evergreen style that suits you best, and stick to that. Evergreen styles can be ideal, because they’re simple enough for anyone to pull off, and they never go out of style. 

When it comes to “basics” or “evergreen” styles, or whatever you'd call them, there's no better person to ask than Calvin Leung. 


Calvin describes his style as “basic luxury”, and says, “I love extremely basic things made really well. My rule is if it's not good enough to wear every day, then I don't need it. I generally wear versions of the same thing every day.”  


Whether you land on basics, or find yourself pulling off a high fashion look, Calvin’s advice for finding what style best serves you is, “everyone needs a period of exploration. You kind of need to go around the world and back to discover what really stays with you. Ultimately, I believe that great style begins with what makes you the most comfortable. Comfort will enable confidence. And confidence is the best form of style. Whatever it is you're wearing.” 

Calvin Leung and Ouigi Theodore
Calvin Leung and Ouigi Theodore, Gap x BKc collab

The ultimate style advisor in my opinion, is Ouigi, who I first met around 15 years ago shortly after he launched the Brooklyn Circus. Through the years his style just gets better and better. With Ouigi, you learn from being around him, that authenticity and the confidence he derives from being true to himself, is what “style” really is. 

Ouigi describes his personal style as “Tailored casual - a bit of old/vintage with a constant eye to the future”, and he says, “I love any and everything that is honest and authentic. I’ve laughed a lot at some of the things I’ve worn in the past and might laugh at what I'm wearing today. But I always know that it’s an honest expression and how I felt at the time, so I welcome that constant evolution. As long as it’s honest.” 

His advice for finding your own personal style: 

“Be honest and try new things. Buy quality over quantity. Do the research and look to the future. Lastly, know how to laugh at yourself, so when others do it (laugh) on your journey you won’t take them serious.”

Ouigi Theodore on set
Ouigi Theodore, The Brooklyn Circus