10 Outfits To Wear In Chicago This Summer Chicago Outfit Guide Summer 2021
The summer travels continue! As most of you know, I’ve been trying to take advantage of this last “normal” summer and see as many new places as possible! Next summer I will be fulfilling my internship credit and the following summer I’ll be graduated and out in the big girl world.
I recognize how unique my situation is, and am so grateful for this chance to really live my twenties to their fullest. While I’ve been loving sharing my travels and food recommendations with you, my roots are embedded in the fashion industry so these outfit guides are a way for me to check all the boxes of things I love.
This past week I visited Chicago for the first time! And while I’m definitely more of a southern living kind of girl, it was fun playing city girl for a few days. As per usual, I changed outfits a gazillion times throughout my three-day stay to give you all kinds fi outfit ideas.
If you’re headed to Chi-town soon, make sure to tune in Wednesday for my full travel guide. In the meantime, here are ten outfit ideas for your summer trip to Chicago!
(click pink text for links)
MORNING TRAVELS
I’ve got to admit, I think I’ve finally mastered the travel outfit. There’s nothing I love more than a matching set— these are a no-brainer outfit and can easily be transitioned from airplane attire to streetwear! These biker shorts and tank top are both from Windsor and are incredibly comfy– with a soft, ribbed material these have the perfect amount of stretch for a long day of travel.
However, I find myself getting a little chilly on these trips. A white zip-up hoodie was the perfect layer to throw over the top. I learned very quickly that the key to Chicago is layers! For shoes, I went with my white sneakers from Dolce Vita. These are called the Zina’s and you’ll see them quite a bit throughout this post. Chicago is definitely a sneaker city, even the Ohare airport gave me a run for my money, lol. These are comfy yet stylish and lasted me many miles throughout this trip.
top // shorts // hoodie // sneakers // bag
photo location ✈ The Rose Hotel
PLAYING TOURIST
On our first day in Chicago, we did all the things- brunch, The Bean, Millenium Park, and more. Although we visited in late June, it was rather brisk throughout our trip. You’d definitely be okay in jeans here if you have a tank on your top half!
I spent the day in this Express high neck bodysuit. I love this piece so much- it comes in a bunch of different colors and is double lined so it can be worn without a bra which is a major plus. I love any piece with this cut because it’s perfect for layering on the gold jewels. On the bottom half of me, I’ve got a pair of boyfriend jeans from Fashion Nova. I love this relaxed fit and although I’m not usually a big fan of rips, these gave off the perfect Chicago vibe.
I did brave the city in sandals! These nude slides are from Franco Sarto and are currently some of my most worn shoes. This nude pairs with everything and they are flat making them tolerable for long distances. I made it about four miles in these before wishing I had on sneakers which isn’t too bad for a shoe with minimal support!
You’ll definitely want a crossbody for this city. Everyone said Chicago isn’t the safest and although we didn’t run into any trouble, I prefer to have my belongings strapped down to me. Plus this style helps keep the weight off your shoulders.
bodysuit // jeans // sandals // bag // earrings
photo location ✈ Millennium Park
DRESSED UP FOR DINNER
We made it back to our hotel and desperately needed to change out of our sweaty city clothes. Of course, I packed plenty, and this tank top and jeans combo were perfect for dinner at The Thorn Restaurant, located on the first floor of our hotel.
This top comes in a gazillion colors and is under $10 from SheIn. I love this champagne and it made my early summer tan pop big time! This tank is on the short side so to keep my food baby from showing I threw on a pair of white cropped flare jeans from Express. These are some of my favorite jeans, reaching for them often when I want a pair of white denim.
It wasn’t too fancy of a place so I stuck with my same nude sandals from the last look! A few simple gold jewelry pieces completed this outfit perfectly.
tank // jeans // sandals // earrings
photo location ✈ The Rose Hotel
BRUNCH WITH THE BABES
There’s nothing I love more than brunch with my girls! I started the morning off in this adorable white eyelet lace top from SheIn. The tiered ruffles are so fun and an off-the-shoulder neckline is so sweet for this occasion.
It definitely is cooler in the mornings here and since most restaurants keep the AC blasting all day long, I reached for jeans yet again. Today’s pair are from SheIn and they are the best I’ve ever gotten from them. They are fitted in the waist yet straight throughout the leg which is such a hard combo to find. These are the perfect wash and have just enough rips for me. I was a big fan of these. Gold lace-up sandals and a pair of statement earrings kept this look feminine!
top // jeans // sandals // earrings
photo location ✈ Thorn Cafe
SIGHTSEEING IN SHEIN
Our day full of sightseeing started off in this light linen romper from SheIn! I definitely recommend airy pieces for the city, but like I said having either your arms or legs covered won’t hurt! This was just the right weight for a morning at Navy Pier. It’s quite windy in this area, so I’d definitely recommend a romper over a dress.
Although it’s a little out of my comfort zone, I went ahead and paired this piece with sneakers. I prefer sandals or heels with 90% of my outfits but sneakers are definitely what you need when spending the entire day out and about. This was the cutest combo!
photo location ✈ Navy Pier
CITY GIRL CHIC
Headed to the Magnificent Mile for some shopping? Or out to lunch with some girlfriends? This outfit idea is perfect for practically any activity the day may bring. Plus, most people we saw on the streets were wearing something very similar to this.
I’m starting off in that same Express bodysuit but in white. It’s tucked into the most amazing jean shorts from Windsor. I really struggle with finding shorts that are flattering and actually fit my waist but these check all the boxes. They are true to size and the perfect length.
To keep things city esque I’m wearing the same sneakers, layering on the gold jewels, and wearing my hair up in a claw clip. I kept my hair like this most of the trip since it was so windy! They don’t call it Windy City for nothing, lol. Anything to keep it out of my face.
bodysuit // shorts // sneakers // necklace // clip
photo location ✈ Magnificent Mile
RIGHT BY THE RIVER
I changed for the Riverwalk as I wanted even more photos and during my live pack with me, so many of you said that this dress would be perfect. Anything easy and breezy is good for this area. This dress is from Romwe and has the most adorable puff sleeves. Of course, I wore this with sneakers as well and popped on a pair of earrings to match.
photo location ✈ The River Walk
DINNER IN THE CITY
There are a gazillion restaurants in this area, it was so hard to choose a place to eat! We settled on deep-dish pizza and although it wasn’t crazy fancy, this two-piece set left me on the cuter spectrum which is something I prefer. Better overdressed than under!
My only mistake with this outfit was not packing a cardigan to throw on over the top. Once the sun went down it definitely was a bit brisk out. Nonetheless, with those nude slip-on sandals and butterfly earrings, this outfit was complete!
photo location ✈ Ghirardelli Store
STREET STYLE SASS
A dress and sneakers are another Chicago-approved outfit idea. I’m used to something colorful and flowy but a ribbed mini dress from Windsor is definitely more city speed. I have a few styles from them and love them all—they’re a little out of my comfort zone but there are so many ways to style them that they are sort of a no-brainer piece to pack.
Of course, sneakers go with everything, or so I’ve been told! I went for my platform Converse this time around and threw on frilly socks from Forever 21 to peek out the tops. If you’re gonna be out all day, throw a denim jacket around your waist for an extra layer!
dress // earrings // socks // sneakers
photo location ✈ The Rose Hotel
TAKE ME TO THE BALL GAME
Seems silly to go anywhere without hitting up the baseball field. The Chicago Dogs stadium is less than a mile from The Rose Hotel, where we stayed so of course we had to stop by. My ball game attire is pretty consistent no matter where I am.
These Express body contour tank tops are incredible. They are super thick and a great length- not too cropped but not quite full length either. I’m pairing mine with denim shorts and high-top converse. For today’s layer, I’m throwing on a jersey and leaving just a few of the buttons done. Gold jewelry helps keep this outfit edgy and cat-eye sunglasses are a must!
tank // jersey // shorts // socks // sneakers // sunglasses // bag
photo location ✈ Dave and Busters, lol
Although it was a short trip I managed to get some awesome content out of it! I can’t wait to share my Chicago travel guide with you next— in the meantime, be sure to catch up on the rest of my travel content here. Any other pieces you recommend packing? Leave em below for the rest of my readers!
With love, McKenz
Latest Post: Weekly Wrap Up #27 2021
Related Post: What To Wear In Charleston Summer 2021
Instagram: styledbymckenz // YouTube: McKenzie Morgan // Pinterest: mckenzmorgan
