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Expert Advice: Packing Light

Chicago… in February


In our style column, blogger Jimi Filipovski explores Chicago in the Killington Chukkas and Mount Walsh Blazer.



"I miss everything about Chicago, except January and February." This quote was woven into the wool blanket on the bed of my hotel and it’s 100 percent accurate. This past month, Timberland asked me to explore Chicago for the weekend. Now, Chicago in February is the equivalent to people beginning work at 4am. It’s probably considered the worst possible month to live in the city. The days end by 4pm and the winds blow right through you to the bone.


Miraculously, that wasn’t the case for me as I explored the city. We got a break from the cold and the snow. Temperatures reached the low 60s and it felt like spring. To meet the up-and-down weather, I like to dress and pack light. The most important pieces in that equation are my Killington Chukkas and Mount Walsh Blazer. I love both of these pieces – they’re perfect staples for any wardrobe.


The boots are great for urban exploring. They’re so light and flexible. They wear like a comfortable pair of sneakers and are perfect for the kind of weather we saw throughout the weekend. My jacket is versatile, too. It’s easy to dress up or down, and shelters me from the always-windy city.


Chicago fashion is typically muted in terms of color. People seem to stick to shades of black, navy and grey. I love navy because it feels formal. My Mount Walsh Blazer is great because the deep navy feels sharp and crisp. It’s a slim cut, which gives it a contemporary feel as well.


I was educated here in Chicago and started my creative career here. It’s always going to have a place in my heart, so across this weekend, I made it a point to roam. I spent some time at a new coffee shop in the West Loop. Millennium Park across the street from my collegiate themed hotel is great. Lastly, the newly renovated riverwalk along the Chicago river is another great place to kill time when the weather’s warm.

Thankfully, the weather in Chicago could not have been more perfect. If only they could have seen my Chicago in February, I believe there would be a different quote on my hotel room blanket.

Photos by Carolina Mariana


Travel on: menswear blogger Anthony Urbano shows us new ways to wear our spring staples around New York City.