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How to Dress for Chicago in April

How to Dress for Chicago in April

Dressing for different climates is always a challenge.

For some, this challenge is fun and exhilarating and inspiring.

For others of us who grew up in a one-climate state and live in crusty sweatpants, graphic tees about farts & sometimes remember to put deodorant on by 2:30pm, it’s confusing and frustrating.

Add carry-on suitcase space restrictions, an epic special event and a cold climate into the equation and it’s plain torturous. (I can barely handle 50° for shit sake.)

How to Dress for Chicago in AprilThe one time New Orleans had no idea that runway status fashion was coming its way.

Take my choice in travel attire for my trip to New Orleans back in January for example. I struggled to strike a balance between “comfortable for all those hours on a plane” and “fashionable”, only to land somewhere in the middle, looking like a WNBA player with an aversion to color. I’ve since learned that color blocking doesn’t apply to outfits that involve men’s zip-up hoodies and yoga pants.

Don’t you worry about me though. I still managed to go to multiple public places that were not airplanes after a quick leap through a perfume spritz.

This trip I head out for on Tuesday is a little different though. Because I’ll be with Rachel Dratch for a good deal of time and I’m feeling like perhaps a t-shirt & flip flops won’t work for a) making great first impressions or b) a cold & cloudy forecast like this:

How to Dress for Chicago in April

Obviously I want to nail what seems to be the holy fashion trifecta of combining comfort, cool guy and protected from the always-barging-into-wardrobe-planning-effects of Mother Nature.

Naturally I’m bringing one of my own shirt designs because, duh, and also, t-shirts = The Mother of All Comfort. But, um, I’m having trouble figuring out the rest of the things that are socially acceptable/required for interacting with other human beings in person. Like pants, but mostly the rest of my upper torso because the last impression I want to give anyone I’m about to exist around is a black eye from the frigidity of my nipples.

Blazers?

Parkas?

The fur of a full grizzly?

Okay so I’m begging for help on this one. Tell me, oh fashionistas/fashionisters of the internet, what do I pack in my carry-on?

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