Insiders know that Stay Classy events are the best way to give back to charity without sacrificing your lifestyle. From concert festivals to pub crawls, Stay Classy events are anything but boring, and always for a great cause. We know you didn’t miss Elemental Experience or Tailgate this year, but you still may not have met the main man behind the brand.

Scot Chisholm is the Founder and CEO of StayClassy.org. But more importantly, his style inspiration is derived from where Zoolander meets Billy Madison, he once wore a spandex skeleton suit for two weeks to raise money for charity, and he’s still mentally recovering from Mom-made Skids that haunt memories of youth.

Don’t let this guy near a department store and beware of your bids for Champion hoodies on Ebay, this thrift store shopping CEO keeps fashion simple, even if it means getting denied at Gaslamp clubs. Get to know Scot in this week’s Local Style Spotlight.

DiscoverSD: What do you do in San Diego?

Scot: I’ve lived and worked in San Diego for over 5 years, starting StayClassy.org in 2006. In just a few years, we’ve been able to help dozens of local charities raise funds through 100+ social events.

This past May, we hosted a 5,000-person music festival in Mission Bay Park, called the Elemental Experience. The lineup featured Matisyahu, Mason Jennings, Pinback and many others, and we were able to raise over $50,000 that was donated to a local charity, San Diego Youth Services. SDYS and StayClassy are currently in a partnership to raise $500,000 to help build a new homeless shelter for kids ages 18-24 who have aged out of the foster care system. We’re doing great so far, but still a long ways to go!

DSD: Outside of work, where can we find you in San Diego?

S: I’m still partial to Pacific Beach bars like Bub’s, The Tap Room, Turquoise Bar, and Firehouse, but I like to venture downtown quite a bit to hit up some favorites there as well, like The Local, The Field, and Bar Basic. I also really like live music, so I try to hit House of Blues, Belly Up, and Casbah as much as I can. Top restaurants include Buon Appetito, Indigo Grill, Strip Club, Masuo's, and Bub’s again (you just really can’t go wrong there).

I guess the common thread is pretty casual, with good food and music. I’m not a huge club dance person, although I can be convinced. I like art galleries, although I hardly ever go. The only one I’ve been to recently is Grant Pecoff’s in Little Italy, my favorite local artist.

DSD: In just three words, how do you describe your personal style?

S: “Cross Coastal Accident”

DSD: Who are your male celebrity fashion icons? Why?

S: Hmmm… I don’t even know. I like dorky celebrities, like the guys who invented Google or Twitter (although I’m not sure most of America would agree that they are even celebrities – but that’s all relative, right?) Either way, I certainly don’t look to that crowd for fashion advice.

I guess if I had to pick a few that really stand out (or don’t stand out at all), I would have to say Ben Stiller in Zoolander – particularly the outfit he was wearing during the “freak gasoline fight accident”. Another I always liked was Adam Sandler’s outfits in Billy Madison – long sleeved flannels, tattered t-shirts, shorts, and work boots. Classic college slob attire right there. 

And on a more serious note (sort of), I’d have to go with Matt Damon’s attire from Good Will Hunting: really old t-shirts and beaten down jeans, the South Boston way… thrilling eh?

DSD: What female celebrity has the best style? Why?

S: This question is easily confused with, “Who do you think the hottest female celebrity is?” – which is a lot easier for a guy to answer. So, I’ll take a stab at that one first. I’m partial to Scarlett Johansson, and it’s not just because I got to luckily sit next to her at a restaurant in LA last weekend. It was definitely that underwear shot in “Lost in Translation” that roped me in for life, I think. Now…whether she has style when she’s fully-clothed is a completely different story.

DSD: A local entertainment expert, what is your go-to outfit for a casual event in San Diego?

S: American Apparel (or CLASSY t-shirt) and Lucky Jeans. In the “winter” complimented with a zipper down hooded sweatshirt from AA or a thrift store. I got a great old-school Champion one of eBay once. Hat optional.

DSD: You’re known to keep it classy many nights in San Diego, what is your go-to outfit for a night out in Gaslamp?

S: Well, usually my answer to the last question satisfies this one too… but on that rare occasion that I actually get dressed up, I’ll usually go button down shirt and jeans with nicer shoes and belt. But let’s just say I’ve been denied entry to many a fine establishment in my day!

DSD: Where do you shop in San Diego?

S: Any Thrift Store, American Apparel, Banana Republic, Lucky, Urban Outfitters, Simple Shoes, Rainbow, REEF Redemption, Puma, can I throw in the Apple Store? I love that place.

Can I add in a few stores I avoid? That’s more fun… American Eagle, Pac Shores, J Crew, QuickSilver, Aeropostale … and any large department store where getting lost is actually something you should be worried about.

DSD: What was the worse “style era” of your life?

S: Well I did wear a spandex skeleton suit for two weeks in an attempt to raise money for charity last year, but I’m pretty sure that’s not what you are looking for here. I’d have to say 5th and 6th grade when I used to wear Skids (those baggy Hammer pants). The worst part about it was that my family couldn’t afford to buy the real brand of Skids, so my Mom, being the seamstress she is, would make me pairs from scratch with this thicker fabric she had laying around. A heartwarming story sure, but I’m still recovering mentally.

Love Scot? So do we. Seek style inspiration from Scot at Stay Classy events in San Diego, or visit StayClassy.org.

Photos by Madison Blades