Chicago: What To Wear, Eat, and Do


The Simply Stylist ‘Do What You Love’ Chicago 2016 Fashion & Beauty Conference is quickly approaching! Whether you are a Windy City native or flying in for the weekend, there are countless things to do in and around the Chicago area to make the most of your time. Traveling to a new city can be tricky because there is no way to know what is good, what is not, and what is worth seeing (especially if you only have a few days), which is why we wanted to share our favorite Chicago restaurants, activities, and #SimplyStylistCHI outfit options! Chicago is a fascinating city with many museums, restaurants, activities, and stores to explore! Chicago’s on-the-go environment may seem slightly overwhelming at first, but we have a feeling you aren’t going to want to leave once you get a taste of life in Chicago. From trending restaurants to Chicago-blogger outfit inspiration, here are some of our favorite things to do and wear in one of our favorite cities, Chicago!

What to Wear: 

An outfit tells all. It says where you’ve been, what you ate that morning, and what type of transportation you used to get there. No one wants to lose out on an amazing opportunity because of an outfit, which is why we can always rely on SteamOne to ready our #OOTD. SteamOne understands the need for high quality garment steamers in the fashion industry, so it is no surprise we will be using their no-drip Garment Steamer to ensure we look our best at Simply Stylist Chicago. Warning: You may find yourself steaming your entire wardrobe!

Browse through some of our favorite Chicago blogger looks below, and be on look out at #SimplyStylistCHI for SteamOne to learn more about their awesome products!

Red Soles Red WineRed Soles Red Wine

Striped ShirtRipped Jeans | Pumps | Leather Jacket | NecklaceCrossbody Bag


Imperfect WonderImperfect WonderJumpsuit | Black Heels | Sunglasses | Black Oversized Bag


The View From 5'2"View From 5 2Wide-Leg PantsLace TopBlack Slip-On HeelsBag


The CHICago Life BlogCHICago LifeDressNude ShoesPink PurseSunglasses


Sequins & StripesSequins and StripesLace-Up TopPleated ShortsLace-Up HeelsCrossbody BagBracelets


Heart of ChicHeart of ChicMaxi DressHeel BootiesSun HatSunglasses


Lake Shore LadyLake Shore LadyOverallsLong Sleeve Top | Wedges | Bucket Bag | Cuff Bracelet


Golden GirlGolden GirlTank TopStriped Shorts | Platform Wedges | Sun Hat | Bracelet Set | Envelope Clutch


Drunk on ShoesDrunk on ShoesWhite Blouse | Ripped DenimBlack HeelsSunglasses | Belt


Olivia RinkOlivia RinkBlue Blouse | White Jeans | Nude Bag | Espadrille Wedges


Where to Eat:

Nico Osteria

Nico Osteria 1

Del Frisco's Double Eagle Steak House

Del Frisco 1

RPM Steak


Three Dots and a Dash

3 Dots and a Dash 1


Where to Go:

Millennium Park

Millennium Park 2

Sky Deck

Sky Deck 1

Navy Pier

Navy Pier 1

Wrigley Field

Apr 23, 2014; Chicago, IL, USA; A general view during the fifth inning of a baseball game between the Chicago Cubs and Arizona Diamondbacks at Wrigley Field. Mandatory Credit: Jerry Lai-USA TODAY Sports

Be sure to purchase your tickets for the Simply Stylist ‘Do What You Love’ Chicago 2016 Fashion & Beauty Conference HERE!

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