In the last decade, the fashion industry has seen the conception of countless T-shirt-centric lines. But few, if any, have proven as adaptable and foresighted as Portland, Maine’s Rogues Gallery, which launched 5 years ago. From being the best-kept secret in menswear, to adding a women’s line, landing in Barneys New York and generating fans amongst the likes of U2's Bono, Rogues Gallery’s rise has been a rapid one.

But that doesn’t mean the brand, or its founders, has lost sight of its roots in the slightest. In fact, Rogues Gallery recently opened its first freestanding boutique in its Portland hometown, and head designer/co-founder Alex Carlton doesn’t seem to be leaving anytime soon. Having spent his childhood in the sleepy New England town of Cape Cod prior to spending time in NYC , Carlton is no stranger to the laid-back lifestyle. In fact he’s a bona fide expert on the city that everyone from John Ford and Stephen King, to Patrick Dempsey and Liv Tyler have called home. Here's the best of Portland, in his own words:

What first brought you to Maine
I moved to Maine 9 years ago, to Cape Elizabeth, which is right outside of Portland. What I loved about Portland was its proximity to outdoor space—fresh air, you’re right on the ocean. It’s great for sailing, it’s got woods that are good for tromping around outside. Coming from NYC, Portland was great because you’re more connected to the outdoors…and in 20 minutes you can be at the Jetport. It has all the amenities of a big city—a lot of culture. The art school has a lot to do with that. There are galleries, coffee shops and alternative movie theatres. It’s got a lot going on for a small town. And I’ve always been interested in coming back to New England. Massachusetts has become pretty developed; Maine isn’t overly developed. It’s the state that captures the most New England flavor. It’s the essence of New England.

How has Portland inspired the line?
We’ve used a lot of regional iconography to develop our graphic points of view. In the early stages of Rogues Gallery we wanted to create a brand that had a regional feeling, one that felt special and connected to an actual place. So we started looking in our own backyard. Maine has a dynamic history: its early colonial history, its ship building history. It also has an amazing agrarian culture. All of these things provided a lot of food for development. Living in Portland also made a lot of our creative development possible. It’s a very easy city to work in: rents are decent. It’s a lot more difficult trying to start a business in, say, NYC.

What is Portland’s creative community like?
The life of the city is a good template for new ideas. There’s always something new on the scene. There’s something in the air, something about the climate of Portland that really fosters creative-minded folks. It’s a very friendly town for people who are artistic. It’s not intimidating. If you look at more established cities, it’s competitive if you want to approach the arts and culture scene. Portland has a more relaxed, small town vibe. So, people are more willing to take risks; they’re less apprehensive.

What spots have you found particularly inspiring?
Definitely the Eastern Cemetery and the Observatory at Munjoy Hills. Movies on Exchange Street; SPACE Gallery on Congress Street is a phenomenal resource for Portland. They have events and concerts, plus they show art. Local 188 is a restaurant and gallery. They just have a great handle on original dishes and are always sponsoring something interesting in the way of visual arts. We get a lot of this sort of fusion, or crossover—an interesting juxtaposition of art and culture.

Portland has quite a foodie culture; what are some of your favorite spots?
Right next door to where our store is located, on Wharf Street, is a great, rustic seafood restaurant called DB Street & Co that’s owned by a guy named Dana Street. His other restaurant is Fore Street, which is on Fore Street. They have amazing free range and organic roasted meats and homemade pastas. There are great places for brick oven pizza. There’s a new place called Bonobo; they have a really creative approach and use a lot of organic ingredients. There’s another place called Aurora Provisions. They have an amazing cold food deli, daily homemade soups, and sandwiches. And Caiola's —they have the best hamburger I’ve had north of Boston. The Browne Trading Company is a world-class purveyor of caviar and has been a great food sponsor for us. I’d cut my tongue out if I didn’t mention them. They’re quintessential Portland.

What about bars?
Gritty's on 4th Street is a great place to get a draft beer. We really like a place called Bubbas; it’s crazy. The first thing that you’re struck with is just the space, the amazing collection of antiques, and the rustic country vibe. It’s filled with taxidermy. You feel like you’ve wandered into some sort of crazy lodge. It’s a great place to hang out. The Downtown Lounge is another one. And a great place for a cocktail is Norm’s. It’s been a regular stomping ground of mine since I got here.

Any great bed & breakfasts?
Bed & breakfasts are a little bit tough...as far as lodging is concerned I tend to put people out in Cape Elizabeth at the Inn By The Sea. It gives you a flavor of the area outside of Portland. 15 minutes outside of Portland you’re on the beach.

What is Portland’s best-kept secret?
I think some of the back streets that are not so assuming are interesting. Like Wharf Street, where our store is, you feel like you’ve stepped back in time. Just hopping on the ferry to Casco Bay, checking out the islands is cool. There are all of these quirky beaches and restaurants. And after a night of dining and drinking, calling a water taxi and taking a moonlit cruise. Nothing beats a midnight cruise on the water: you and your friends, and a boat and captain at your disposal. And, if you’re feeling indulgent, the hot stone spa treatment at Nine Stones.

~Alisa Gould-Simon

Go There:
DB Street & Co, 33 Wharf Street, (207) 775-0887
Fore Street, 288 Fore Street, (207) 775-2717
Bonobo, 200 Brackett Street, (207) 347-8267
Bubbas, 92 Portland Street, (207) 828-0549
Down Town Lounge, 606 Congress Street, (207) 773-1363
Norm’s Bar & Grill, 617 Congress Street, (207) 828-9944


Second photo by ginandtonic1978 via Flickr
Fourth photo via Spirits Alive
Fifth photo by Lall via Flickr
Sixth photo by Novo a go-go via Flickr
Seventh photo by Space538 via Flickr
Ninth photo by MS2171 via Flickr
Thirteenth photo by Eva8 via Flickr