Seven Days of Dapper: Shana Natelson

Portland, Maine has a unique dapper style all its own, and we’ve got a brand new Seven Days of Dapper featuring Shana Natelson to prove it! I’ve personally been stalking Shana’s style on the Jack Tar 207 Facebook page for some time now and was finally successful in getting my hands on some of Shana’s swag to share with our readers. Here are her stats:

Shana originally hails from Taos, New Mexico and has been happily living in Maine since 2006, slowly incorporating more flannel and plaid into her wardrobe. In addition to her role as Location Scout/Photography Assistant for Jack Tar 207, Shana Natelson serves as the producer, writer and actor for Speak About It, a performance-based educational program about consent, boundaries and healthy relationships primarily for college students. As a producer, Shana has helped encourage thousands of students to have a dialogue about sex with their peers and partners. Shana and Speak About It are currently based in Portland, ME where she talks about sex, dabbles in men’s fashion and plays in the sunshine, not unlike a puppy.

Day 1: East End Portland, ME




Sometimes it snows in Maine. Ok, it snows a lot in Maine. But outdoor adventures are no excuse not to look good, right?

Outfit details: Flannel-lined pants from J Crew, fleece-lined boots from LL Bean, Lucky Brand belt stolen from my sister, NAU wool coat, olive sweater from H&M, rugby shirt from Polo, hat courtesy of TT Tappan.

Day 2: Cocktail party



I love this combo because it’s sharp but not too fancy. The white blazer definitely steps things up a notch, but the black v neck keeps it casual.

Outfit details: White Blazer from Express Men, Hanes black v neck tee, maroon pants from H&M, shoes from Bass, generic hankie, flea market belt.

Day 3: Taking a coffee break from the office




This is one of my favorite outfits, this sweater goes with everything. I also like wearing bow ties with jeans, again classing up the casual look. Bow ties are making a huge comeback in fashion right now, and I love to play with the traditional formality of bow ties by combining them with jeans or boots. Details are important to me, so I like wearing bow ties that you have to tie.

Outfit details: Grey sweater from J Crew, oxford from Polo (via Goodwill), bow tie from Brooks Brothers, belt from my alma mater Bowdoin College, jeans from Jack Jones, Bass boots, leather bracelet and socks from H&M, Ray Ban glasses (yes, they’re real ha!)

Day 4: Throw some spice in the workweek!




I was recently introduced to Bonobos, amazing men’s pants that make your butt look great. I’ve played ice hockey for almost 20 years, so I definitely appreciate a pair of pants that play to my strengths, if you know what I mean. The pants aren’t completely solid, the shirt is herringbone with elbow pads, and the tie is gingham: a perfect combo to feel good at the office.

Outfit details: Pink pants from Bonobos, shoes from Bass, socks from J Crew, shirt from Zara in Madrid, Brooks Brothers tie, vintage lobster tie bar, Jack the Pug from LK Weiss.

Day 5: Look good, feel good



I also try not to take myself too seriously – that buck was a great conversationalist! This is something I would wear to the office or during a Speak About It performance.

Outfit details: Gingham shirt from J Crew, vintage skinny tie, Lucky Brand belt stolen from my sister, mustard pants from TJ Maxx, Bass shoes, socks and buck from LK Weiss.

Day 6 AM: These are my fancy pants




I love color accents. Moving from New Mexico to Maine, we see the sun a lot less up here. And I love to wear bright colors when it’s overcast, bring some pop to the grey. This suit is a great charcoal grey, but I like to keep a little bit of spice in the socks and the bow tie.

Outfit details: Suit from Gap Men’s, shirt, socks and suspenders from H&M, shoes from Goodwill, Ray Ban sunglasses, hankie from Jack Threads, gingham bowtie from TJ Maxx.

Day 6 PM: Saturday night date night




If I have a loud shirt/tie/blazer/pocket square, I try to rock more mellow pants so it’s not distracting, and then pull everything together with socks. I love a good, well-fitting blazer that can elevate any outfit to slightly more formal without being too fancy. I also love playing with patterns, texture, colors. I think it’s ok to have some contrasting patterns (ex: stripes with gingham) as long as they’re complimenting and not competing. The trick to patterns is to make it look like they were supposed to go together. Gingham and stripes? Plaid and polka dots? As long as they’re a similar size or color palate, it’s like peanut butter and jelly.

Outfit details: Navy blazer from Target, Express Men’s shirt, J Crew tie, vintage tie bar, Bass shoes, maroon pants from TJ Maxx, socks from H&M, mustache tie bar (gift), pocket square from Penguin, Lucky Brand belt stolen from my sister.

Day 7: Sunday shoot


The red chair is a staple in our Jack Tar 207 shoots, we’ve all had some nice adventures together.

Outfit details: Timberland fleece-lined boots, socks from H&M, jeans from Jack Jones, Express Men’s shirt, bowtie from TJ Maxx, chair on loan from St. Lawrence Arts Center in Portland, ME.

Behind the scenes…



Behind the scenes at a Jack Tar 207 shoot is no excuse to leave your tie at home. I’m kind of a sucker for J Crew, their men’s clothing fits my body type really well, and it lets me play with colors. And of course, I’m pumped to be sporting the first-ever, so-far-one-of-a-kind-custom Jack Tar 207 tee.

Outfit #1 details: Blue pants, gingham shirt and necktie all from J Crew, Cole Haan shoes, vintage tie bar, vest from Zara in Madrid, gifted belt buckle.

Outfit #2 details: Original Jack Tar 207 t-shirt, Hanes undershirt, Bass boots, jeans from Jack Jones, gifted cowboy-style belt buckle, vintage bandana.

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