What To Wear In Chicago One Of Our Editors Is Sharing How To Pack For Holiday Trips In Cold Destinations


Mother Nature decided to bless Chicago with an early snow shower this year.

According to Farmer’s Almanac it will be another freezing, frigid, and frosty winter. In fact Winter 2020 is already being dubbed "Polar Coaster” for the dramatic ups and downs we will potentially be seeing.

If your holiday travel plans include visiting cold climate destinations, we have got you covered on what to wear and what to pack to survive the cold and still look chic AF.

I have shared a few times my favorite vegan + cruelty-free winter coats that are so warm I find myself so warm I have forgotten how horribly cold it actually is! Make sure to invest in a solid winter coat, my favorite is Hoodlamb’s Nordic Parka.

Find the whole collection here.

What to wear for a Winter Chicago Vacation from a Chicago Fashion Blogger, cute winter outfits

Layering Essentials

Tights, leggings, thermal wear. These are the foundation of a warm winter outfit. When you have these crucial elements in place, the rest is just frosting on the cake.

The base of every winter look contains one or more of the previously mentioned items. Wear your favorite dress, just make sure that your layered properly underneath, and take advantage of the turtlenecks layered under dresses trend that is a beautiful example of form and function.

I honestly like to keep my actual outfit looks fairly simple throughout winter, and by simple I mean a combination of sweaters or turtlenecks paired with dresses or leggings. I like things that can tuck into my thigh-high boots easily. The first day of snow is always beautiful, but day 2-120… not so much, especially in urban settings. I don’t like anything to drag close to the ground or be cumbersome getting in and out of the car all day, as I am usually running from appointment to appointment for clients and production.

More details below on the elements of layering and what to pack when traveling.


How To Pack For Cold Climate Destinations And Still Look Cute Chicago Fashion Blogger Sararose Krenger
How To Pack For A Winter Chicago Vacation Tips From A Chicago Fashion Blogger Sararose Krenger

How To Quickly Dress Up Basic Winter Outfits

Headbands, Hats, Scarves

Headbands, hats and scarves are extremely easy ways to up your chic factor, without compromising on comfort and warmth. If fact most of these elements lend to bringing warmth to your daily attire. I’ve really gotten in to the padded and beaded headband trend. Its like wearing a crown but in a super approachable, daily way. I have always been a major hat fan, my latest favorites are from Hatsmithe, female founded and vegan + cruelty-free. I love color coordinating my hats and headbands to scarves with pretty prints and patterns. These are easy affordable ways to change up your overall look when wearing the same series of jackets or coats for an extended period of time (i.e 6 months or more).

Earrings

Another favorite fuss free way to dress up a warm layered look is by statement earrings. Earrings are probably my favorite accessories to wear, because I don’t feel them. I like them light, yet bold and big. They make chunky sweaters a bit more feminine and can also lend to that ethereal vibe i love so much about headbands.

Lipstick

Nothing says “put together" chic” like a pop of matte long lasting lip color. It is a quick minute fix to feeling drab on cold blustery winter days.

Boots

I don’t know where I would be without my thigh-high boots! Literally life savers, because they add that extra layer of warmth and also look extremely luxurious. I have a collection of thigh-high boots that is continuing to grow. I consider them my pants in the winter, and have invested in some fun prints and colors to change up my everyday outfit.

Tights

Tights can be vibrant statements throughout the winter. Take advantage of the abundance of colors, prints, patterns, and textures that there are and don’t be afraid to play and mix and match. Tights take up hardly any room in a suitcase yet lend to a layer of warmth and a pop of personal style.


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SHOP THE LOOK:

vegan chunky sweater Hoodlamb vegan fashion cold winteres

LADIES' RIBBED SWEATER

$78 | Hoodlamb (vegan)

pink holiday dress Freepeople burnout slip dress with ruffle

Olivia Velvet Burnout Slip

$88 | Freepeople

Vegan thighhigh boots for winter Freepeople Best Vegan Fashion Blogger Vegan Fashion Chicago

Vegan Oakland Over-The-Knee Boot

$198 | Freepeople

black velvet padded headband Prada Vogue Best Vegan Fashion Blogger Sararose

ASOS DESIGN padded headband in black velvet

$13 | ASOS