What to Wear

In Chicago seasons, there are beautiful days and there are ugly days. There aren’t very many in between. A rainy day can be fun and glamorous in the Chicago summer, twirling in a sun dress in the vacant suburban street and pretending you’re in a music video (no? just me?) but rainy winter days are everything but glamorous. Icy winds and cold rain slap you in the face and puddles love to find you when you’re not wearing rain boots. Luckily, I found this Fashionista smiling and laughing walking to the library through the harsh rain.

Don’t give up on your style because of the rain. Hunter Boots are a little too familiar for me so I usually end up weather protecting my leather boots like this Fashionista did. Riding boots keep it casual for any situation and when you get to your destination, you don’t feel like you have to trudge with heavy rain boots on. Her water resistant jacket is perfect because it’s warm, but still lighter than a winter parka. This is one of my favorite jackets that The North Face makes.

Using the red scarf as her statement piece, this Fashionista brought some color to a gloomy and gray day. Big pearl earrings frame her face and make the look classy and put together. If you are rushing to get out the door, pearl earrings and thrown up hair is a go-to. Don’t even get me started on the bubble, clear umbrella. Here’s the scene: walking in the rain to class, umbrella flips up in the wind, try to fix it, drop your cell phone, walk into class, eyes watering, mascara seeping down your face, hair going crazy, look around, get the knowing nod from the other girls wiping under their eyes. Familiar? The bubble umbrella solves that and it is my new obsession. My mom bought me one last year and I use it all the time. My friends like to join me under the dome of safety because their umbrellas just aren’t the same. Seriously, get one. You won’t regret it.

One Simple Change: For brunch in warmer weather, this casual look would be perfect paired with a peplum top. Peplum tops originate from the ancient dresses of Greek women. Peplums are popular on dresses and tops this season and they are for both casual and formal situations. This top is casual and mixed with the dark jeans, riding boots and pearl earrings this Fashionista is wearing would be perfect for a brunch date.


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