Ohh Chi town. What a fabulous city! I’ll be sharing all we did and all of my recommendations next week, but for now I wanted to go ahead and share my Chicago outfit recap and give you some ideas of what to wear in Chicago for your next trip. We were there over Labor Day, and minus a few showers, the weather was perfect. It makes it easiest to shop all the looks in one place in these Instagram roundups, so.. happy shopping!

WHAT TO WEAR IN CHICAGO

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This lightweight thermal style top is so easy to throw on! It comes in several colors and can be worn on or off the shoulder. It looks adorable with a lace bralette underneath it, too. I’ve worn it with jeans, shorts, and even sweats lounging around the house. It’s great to layer over, too. I wore it with my favorite retro sneakers and these jeans with which I am still oh so obsessed.

Top // Jeans // Sneakers // Bag // Luggage  // Tote

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I wore this cute jumpsuit out for our first night. It’s a perfect little date night piece and actually can be worn to work depending on how you style it, too. I love versatile pieces like this! Especially because it’s such a simple, but classic look. It’s a great price point so the CPW (cost per wear) is great on it. I’ve already worn it several times and think it will be one of my go to pieces when I don’t want to think too much about what I’m wearing.

Jumpsuit // Heels // Bag // Necklace // Bralette

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Give me alllll the blazers. Especially plaid ones for fall. This one wraps around and secures with a belt so you can wear it more like a top. You can also take the belt off and wear it as a classic blazer! I paired it with white booties to offset the darker colors a bit. I’ve been reaching for these booties time and time again still when I want my outfit to have a little bit something different or trendy to it.

Blazer // Jeans // Booties // Bag // Bralette // Sunnies

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I literally got stopped every hour on the street or in restaurants with someone asking me about this jacket. It’s a show stopper and is SUCH a good statement piece that isn’t too over the top. I love it over a slip dress, too. The detail is insanely gorgeous. I kept the rest of the look simple with classic jeans, black booties, and my latest designer bag that I keep getting so excited over every time I pick it up.

Cami // Jacket // Jeans // Booties // Bag

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I absolutely love the jumpsuit. It’s a loungewear style jumpsuit and is the easiest, comfiest darn thing ever. I seriously get so excited to come home after work and put it on. Is that sad?! Whatever. It’s a great piece and it’s been marked down recently, so jump on it (pun intended) ASAP. I also love this one. Perfect for hanging out and ordering room service!

Lounge Jumpsuit // Bralette

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Ohh my this slip dress may be my new favorite purchase. I want it in every single color under the rainbow! Its such a good piece. It’s a classic silhouette, but has a subtle sexiness to it. I love it dressed up like I wore it here fore date night, but it’s adorable styled casually with sneakers and a cardigan sweater. SUCH a good piece that you’ll have and wear for years and years. I love slip dresses so much!

Slip Dress // Bralette // Jacket // Heels // Bag // Necklace

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This sweater is a must in at least one of the colors it comes in. Seriously! It’s such an easy, versatile piece. I love it styled so many different ways. It’s super affordable, too. This faux leather mini is also a steal. I’ve worn it almost once a week since I got it. I added my latest convertible bag for a pop of color. You can wear it as a top handle, a cross body, or a back pack. It’s like three bags in one and comes in several colors! I thought this wine color was great for fall though.

Sweater // Bralette // Skirt // Booties // Bag // Necklace

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Always all about comfort when traveling and these joggers are the definition of that. Plus, their really cute and soft! I’ll be wearing them on repeat whether I’m traveling or not for the next several months. I paired them with my favorite crew neck tshirt and a denim moto jacket so I don’t get cold. I’ve been wearing these sneakers non stop when I want to be comfy, but cute. They are so comfortable and I love the retro style. This luggage also comes with a matching carry on and is available in a few fun, metallic colors.

Tshirt // Joggers // Jacket // Sneakers // Luggage // Tote // Bag // Sunnies 

I wear a lot of the same every day jewelry and beauty products when I travel, so I wanted to link all of that together for you all to shop, too.

CLICK BELOW TO SHOP EVERY DAY JEWELRY & BEAUTY

Stay tuned next week for my full recap of our trip and all my suggestions if you’re planning one there, soon. I think this is one of the longest lists of restaurant recommendations I’ve ever had for a city! SO many good ones that we went to and that are on my list for next time. Until then, catch up on my latest travels in my Seattle Travel Guide and my Oregon Coast Travel Guide.

Hope you are all having a fabulous week so far! XO