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Expert Advice: Ways To Wear Plaid

Aaron Wester takes us from day to night in NYC

In our new series, top style bloggers show us their favorite ways to wear Timberland gear. Aaron Wester of The Modern Otter kicks it off with his three favorite ways to wear plaid in the city.


It’s 5am. The sun hasn’t come up yet.

The sound of crickets and swaying branches echoes throughout the room. My boots are on the floor by my bed (because they’re all I ever wear in the Fall) and I’m fast asleep…

Until a yellow cab speeds by my apartment blasting its car horn, waking up the whole building -  I roll over and remember I’m in Manhattan, not Upstate New York (where I grew up), and the crickets are coming from the white noise app on my phone, not the forest outside.

I’m a rugged adventurer, but city streets are my forest trails; sky scrapers my trees.

And just like any other outdoorsman, Timberland has me fully equipped for the trail ahead. Check out my three city-style looks below with Timberland’s new double-layer plaid shirts (in red, blue and black iris). I take full advantage of their versatility- from work to weekend.


Central Park Bound


I love exploring in the park - the changing leaves and winding paths are a refreshing escape for everyone in the city. For my afternoon, I wrapped my Men's Allendale River Double-Layer Plaid Shirt around my waist and kept it classic with a denim jacket and white tee. The look is both form and function.

When the temperature drops, I can throw the plaid shirt on for a layered look. I’m all about military styling this Fall, so I paired my boots, Men’s Earthkeepers Original 6-inch Boot with fitted joggers and thick socks. Well-made boots are a requirement in this city. The pavement is surprisingly hard on any pair of shoes, so you want to ensure you’re investing in quality, like these.


On The Move

I’m a menswear blogger. I run all over the city each day and my camera never leaves my side. I need clothes that fit well and are versatile for wherever my adventures take me. For my first look, I paired the Men's Warner River Slim Fit Double-Layer Shirt  with a quilted vest and denim jacket, my two go-to layering pieces this Fall.

They pair perfectly with my staple Fall boot, the Men’s Earthkeepers Original 6-inch Boot - great for all day wear and sturdy enough to last.

I know I can always ditch my denim jacket and still look stylish with the vest and Warner River Slim Fit plaid shirt. I topped it off with a wide brimmed hat for an on-trend outdoorsman look.


Happy Hour

My favorite city nights begin with happy hour. As the sun goes down, the city begins to hum. I look for the nearest rooftop to watch the lights come alive.

I want to look put-together for the evening and luckily these shirts are just as easy to dress up as down. I paired this red Men’s Allendale River Double-Layer Plaid Shirt with a leather moto jacket and gray trousers for a rugged yet tailored look. All I need is a motorcycle and I’ll be set!

One shirt, three ways. I’d say I’m well equipped for the trail ahead. 


Aaron Wester is a menswear blogger based in New York City.