What to Wear Downtown

I grew up in southern Indiana, and while I was near a suburban area, my upbringing was largely rural. When you are from a smaller town or rural area, visiting a major urban area (like downtown Chicago) can seem so daunting!

I have friends coming to town this weekend, and as I am telling them what to bring, I am planning my own necessities for spending several days downtown.

What to wear:


This jacket is my go to for any trip- urban or rural. It is perfect for city trekking because it comes in any color, it has pit zips so you can wear it inside or in warmer months without sweltering, it is waterproof, and the best part: it folds into it the pocket. When it is packed into the pocket and zipped up, it is smaller than a paperback book, which is perfect for tossing in a bucket bag or daypack.


In the city, it is totally okay to wear any wild and crazy color that you feel compelled to wear! Admittedly, I gravitate towards gray and black these days. Black jeans are easy to wear with any top or shoe, and wearing dark neutrals is the fastest way to feel sleek and pulled together.


Sometimes in the park or in a theater, it can get pretty chilly- even if it was an otherwise warm day. It is crucial to pack an extra sweater or fleece, even if it was warm when you left! I was kicking myself during brunch on the patio last week when the sun went behind the clouds and the temperature suddenly dropped ten degrees! Please take an extra layer.


#1 Rookie mistake: wearing cute flats downtown. Locals cringe when they told their friends to wear tennis shoes and they shoe up in flats or flimsy sandals… or heels!

Here’s why:

  1. You will be walking to the train and to the bus and to shops and museums and through shops and museums and up stairs and down ramps and will run to catch the train or cross the street and stand still waiting in line… your feet will be killing you even if you wear your best, most supportive shoes. So wear your best, most supportive shoes.
  2. You shoes are going to get a little nasty. People pee in these streets, and worse. Seriously. If you have sandals or flats your feet will be as dirty as the bottoms of your shoes. Keep this in mind! When I wear sandals downtown, I am sure to choose a pair that is about an inch off the ground (still a flat, but with a slight elevation.) These flatforms are probably a great way to navigate the city!
  3. The weather can be different in each neighborhood. Even when it is sunny with clear, blue skies at my apartment, it can end up being cold and rainy downtown or in another neighborhood. When it is raining, some parts or the street or subway flood. Rain boots you can walk in are essential.
  4. Sometimes you want nice shoes. It is okay to wear flats or heels to the show you are seeing or party you are going to. Just take them with you, in your bag, and change when you arrive. Anyone who works in the is going to wear sneakers to work and change when they get there. When in Rome…


You need something to carry your wallet, extra sweater, rain jacket, flats, external battery, water bottle, and snacks in. This reversible option is my favorite! _9512099.jpg

Will You Wear “Dad Clothes” this summer?

I don’t know if this is just 90s norm-core trend, or if my parents just know timeless classics when they see them, but I have been seeing EXACT replicas of clothes and accessories my parents wore in my childhood… and STILL use!

Exhibit A: Dad’s beach shirt
25 years ago, this shirt served as a light options for special occasions in warm summer months. Today, it is the single-button beach shirt.


See also: Grey stripe

Exhibit B: Mom’s fanny pack

Before and after the short period where I found fanny packs weird and uncool, I loved m mom’s primary color-block fanny back. The main body of the bag was royal blue, with a multi-functional red pocket topped by a purposeful yellow zippered stash. On our trips to the local theme park, Holiday World, you could usually find an instant camera, a tube of sunscreen, and a visor! The fanny pack hangs in the same spot by the door, but now I feel that my sister or I may be more apt to wear it than my mother!


See also: Hologram fanny

Exhibit C: Mom and brother’s matching denim baseball hat

Soccer games in May. Freezy–pops and hot dogs, and my 4-year old brother matching mom in a pair of identical denim baseball hats, topping their identical blonde heads. They both still wear these hats! I’m thinking we should expand to a family set, now that 90’s norm-core is here to stay.


See also: This cap

Exhibit D: Sisters in jelly sandals

I feel like my sister and I wore these gems to church and the pool, because they were squishy and sparkly so you could basically wear them anywhere? In 20 years, that fact hasn’t changed. Sneak these to a meeting or rock them on the beach.


See also: Rainbow/ USA

Exhibit E: The scrunchie

I definitely wore a dark red scrunchie every day of 5th grade. I like this metallic number!


See also: This rainbow pack

April Showers bring chilly hours!

It’s getting warmer outside, but it is also getting… wetter. So we all want to expose our kneecaps and elbows… but the rain brings along a bit of a chill!

If you have ever come in from the rain in your light spring clothes only to sit in front of the A/C with no jacket… you know how important it is to have some spare spring sweaters- for your bag, your car, even to keep at your desk! As we are anticipating a drizzly week in the midwest, here are some mood and shoulder warmers to the rescue!


Each cardigan below is $25!
For pulling over a light denim dress when you want warm arms and a place to store your phone…. we need some millennial pink with pockets!

But I ALWAYS need a green option, and the mossy short-sleeved choice adds some nice color to my otherwise hunter green choices.

Spring Upgrades and Earth Day!

I am quickly settling into a carefree springtime attitude, and am making lifestyle adjustments to match my demeanor.

  1. Health

    When we “sumitted” the Grand Canyon, I was full of a sense of accomplishment, but also filled with a new determination. Now I had confirmation that I am strong, I wanted to maintain that powerful feeling… so I took the plunge and committed to a month of Brookly Boulder’s (Chicago location) “Beginner to Badass” program.

    This led me to the Earth Day event, Camp BKB. Where I got this amazing shirt:

    save the

    t-shirt photographed by my sister in our tent

  2. Feet!

    Seriously, one of the best things about the warming weather is giving your toes a chance to breathe! I am eyeing these for the business in the front and these for the party in the back.

  3. Bright (healthy) skin

    When I was at Camp BKB ringing in Earth Day, they had representatives from LUSH giving complimentary facials. After being slathered in mango and having my face massaged with a warm towel, I was given a card with a description of my treatment. I had The Sacred Truth mask, which must be purchased at the store so that it remains chilled. Made with fresh mango, this mask has a short shelf life but is soooo worth it! My specialist cleaned that up with the Eau Roma Water as a toner. Finally, and this was a game changer, she used this Vanishing Cream, because I said I wanted more even color and texture on my skin. This was amazing! For the next two days, my face was baby-smooth and an even color all across. I was floored. Now that I am browsing this purchase, I’m swallowing hard at the price but sucking it up because I know the results.