How to Look Preppy in Winter (and Still Stay Warm)

Chicago has been on my travel wish list for so long. I have always love city adventures more than island travels. From wandering around the city to people watch on the busy sidewalks, it’s never boring to explore how a city works by observing and being exposed to different cultures.

ASOS BERET / ASOS COAT / MADEWELL SWEATER (SOLD OUT, SIMILAR HERE) / MADEWELL SHORT / DR. MARTENS SHOES / YSL BAG

Cloud Gate at Millennium Park

Millennium Park is like a pretty oasis in the concrete jungle and is the landmark of the Chicago city. Located in the center of the city, the park features a few public art pieces especially Cloud Gate. Cloud Gate is a giant stainless sculpture that reflects the amazing skyline of the Chicago city.

Because of its look-alike shape, Chicagoans have nicknamed the sculpture “The Bean.” The artist Anish Kapoor got inspired by liquid mercury and it takes 5 years from design to finish. They shipped these giant stainless steel plates all the way from California. And these plates were seamlessly welded and assembled in Chicago. I love how everyone interacts with this piece of sculpture at Millennium Park. This is what public art should be – it should be where people can get close to it.

My Preppy Winter Outfit

Chicago is famous for its windy cold winters. Since I’ve survived several Boston winters, I came prepared. It’s indeed that Chicago winters are brutal, but not as bad when layering with right items. For my base layer, I wore a long sleeve t-shirt from Uniqlo’s Heattech thermal extra warm. It’s soft, fitted, comfy, and warmer than normal Heattech. Then I added a flannel shirt, and piled on a wool-blend sweater. I also inserted a down vest from Uniqlo and finished off the outfit with a wool coat. I love layering a vest under the coat because it provides extra warmth without looking too bulky.