With holiday season ramping up and a calendar full of festive parties to attend, SG readers know you don’t have to be in the spotlight to care about your personal style. While it’s fun looking to celebs for sartorial inspiration for parties and events, it can be more helpful to simply look around you. Seeing what friends, co-workers, even strangers on the street are wearing may give you new ideas for your own winter wardrobe.

That’s why I decided to document the personal style of a few of my well–dressed friends — real guys I know in NYC with killer style — in this series, Style in Real Life.

Ryan Jones, filmmaker

I first met Ryan years ago when he was working at a news magazine’s online destination as a videographer. My career coach had sent out a frantic email to her clients wondering if anyone would like a free, in-person session…that night. The news magazine was doing a segment on the rise of career/life coaches, and wanted to film her in action. A free session? I was in.

Whatever preconceived notion I had of filmmakers’ style was put to the test when I showed up and met Ryan. My idea of dressing for ‘behind the camera’ was informed almost exclusively by directors like Steven Spielberg and Brett Ratner…not exactly shining beacons of style.

But far from being decked out in a scrubby t-shirt and jeans, he looked much more put-together than I did even, and I was coming from work at an ad agency in the city (though, to be fair, I’d pretty much checked out by then…hence the dirty hair…)

But still! He looked like he’d come right from the barber, with a smart, closely cropped haircut, with a v-neck sweater on over a button-down. I remember thinking, Where’s his beat-up baseball cap? Where are the ratty sneakers?

Cut to three years later, and I’d (slowly) put the advice of my career coach into action, leaving advertising to pursue writing full-time. Among other small gigs, I’m freelancing for a men’s website…where Ryan happened to be working. Oh, and it turned out we lived about six blocks from one another in Brooklyn.

We quickly got up to speed on each others’ lives and our respective creative and personal pursuits. We still crisscross the neighborhood catching up, and even for a walk through the park with his so-cute-it’s-not-fair-to-other-dogs dog, Archie, he takes the time to look put together.

On the importance of fit:

“I see so many guys walking down the street, and it’s clear they’re just wearing clothes directly off the rack, without tailoring any of it. I realize I’m preaching to the choir, but it makes the biggest difference in the world. If I get a dress shirt, it may fit on my torso, but I know I’m going to have to get the sleeves shortened, or they’ll be down over the wrist. For me and my body type, the sleeve shortening is key.

Take this coat, for example. People regularly stop me on the street to compliment this coat. It’s just from Banana Republic, a few seasons ago, but I took it in and had the tailor shorten the sleeves and maybe take it in slightly…actually, I don’t even know if that’s true. Really, it was all about the sleeve. When it goes down to your thumbs, you look like a child in your clothes. And shlubby, to boot.

About his outfit:

“Most of this is J.Crew. Once I find a brand that I like, I tend to be very loyal to it. Mostly because if I like something, that means it fits really well, and why wouldn’t I make shopping easier on myself like that?

RYAN’S STYLE PROFILE

My style in three words (or less!)

Fitted, preppy, and polished

My first “fashion” memory

Need I say more? This is me at age 2 or 3, though I have to give all credit to my mom who dressed me.

Ugly sweater parties: Suit up, or skip ’em?

I’m going to an ugly sweater party this week, and I haven’t had time to procure one, but I would say definitely suit up, because it’s fun and I like the exercise of being creatively funny. It’s just as gratifying as having the perfect suit for an event, I think.

Holiday party outfit go-to

I’m a sweater-over-Oxford-shirt kind of guy. Sometimes I’ll throw a blazer over it or a tie, but not usually both, because the combo is a little too formal for the occasion. It just feels right. This is what I wore to a holiday party last year. The cheesy gesture is also incredibly stylish….right?

Favorite “splurge” clothing brand

I don’t know if I have a favorite splurge brand, per se, but I’ll tell you that my favorite splurge purchase was a good pair of Red Wing boots, which were just shy of $400, but they look great and they’re completely water-proof, so I purposefully jump in puddles and snow piles just to celebrate their quality.

I’m always surprised when people compliment my clothes, especially shoes, because I just don’t think people are looking, but I get compliments on those boots all the time.

Favorite “steal” clothing brand

Uniqlo. It might not be the absolute highest quality, but you’ll get more than enough mileage out of what you buy there. Plus, their stuff fits well on me without alteration.

A man’s personal style is important because…

It gives you confidence.

I don’t have what you might call “leading man looks,” but when I’m making an effort at what I’m wearing, I feel more sure of myself, and also that I’m projecting the fact that I care enough about whatever I’m doing to put thought into how I look.  

Whether walking into a job interview, a first date, or just going to the subway, feeling good about the way you look, I think, gives you that little boost to make a difference.