What I Wore in the Windy City

I just came back from a weeklong trip to Chicago, where I met up with some college friends, made new blogger friends, went pescetarian (more on that later), and attended a good friend’s wedding. Here are three different looks I wore while in the Windy City, ranging from super casual to super glam, as well as some quick notes of what I did and how I wore my hair!

Cafe Comfort

chambray top-black joggers-statement necklace-afropuff | KlassyKinks.com

Express One Eleven Contrast Lace Bralette | Shabby Apple Chambray Shirt | Necklace (completely forgot where it’s from, similar)H&M Black Joggers (similar) | Nike Kaishi Anthracite/Metallic Gold

You might have seen this outfit already since I shared this photo in my post about Malia Obama choosing to attend my alma mater, but I met up with my lil sib from college at Filter Cafe in the Wicker Park neighborhood of Chicago. I live for cafes and this one was so spacious and had huge windows – which provided the perfect lighting to capture all the melanin Rachel and I were serving.

Why I Love This Look: Hands down these pants, which I bought in H&M in Abu Dhabi, are the most comfortable pair of pants I own. Joggers can look frumpy (unless you’re wearing heels), but the cutouts in these ones make them look stylish. But even more comfortable than my pants are two things you can’t see – a bralette and sneakers. As someone who’s struggled with small boobs and pointy nips, I didn’t think I could go without a pushup bra, but I’ve *finally* (took me darn 25 years, ok maybe 20) stopped caring about big boobs. Unlined, unpadded, heck, wireless bras are my new move! Though you can’t see them, the sneakers I was wearing, and pretty much wore all week, are these cool set of kicks by Nike that I first saw while I was at Lord & Taylor buying the shoes in this outfit. I’m not really a sneakerhead (my mom forced it out of me in the 8th grade), but the gold stripe had me sold!

Hairstyle of choice: A good old afropuff 😀

Chic Monochrome for a Lunch Date

monochrome-topshop leather jacket-gap pure body modal tee-hat-silver heels-ripped jeans | KlassyKinks.com grey monochrome outfit-gap pure body modal tee-hat-silver heels-ripped jeans | KlassyKinks.com grey monochrome outfit-gap pure body modal tee-hat-silver heels-ripped jeans | KlassyKinks.com

Gap Pure Body Pure Body Modal Short-Sleeve Tee | Boohoo Stone Statement Plate Necklace | LOFT Black Skinny Jeans (DIY ripped) | TopShop Polly Faux Leather Jacket | Icing by Claires (don’t judge!) Packable Hat (similar) | Michael Antonio Jaxine Metallic (less than $25!) | NYX Makeup Bag

I met up with Lauren of Diaries of a Wannabe Rich Kid, whom I met online in my bloggers group! She introduced me to a BOMB eatery called The Little Goat, where I had one of the most delicious shrimp and grits meals I’ve ever had. We then took photos of one another, ya know, since neither of us have Instagram husbands to snap our pics!

Why I Love This Look: This Gap body tee was on sale (it’s still just $15!), but more importantly, feels like a satin bedsheet against my skin. My DIY LOFT ripped jeans + quilted leather jacket are a look I wear a lot, but adding these simple silver heels that I bought for my brother’s wedding three years ago (!), a statement necklace, and a hat that doesn’t get squished while traveling made this outfit into something worth talking about. Plus, the little clutch I’m holding actually came for free.99 when I bought a ton of makeup at NYX!

Hairstyle of choice: Dry bantu knot out (video here)

Lilac Wedding Guest

purple dress-cutouts-mignon-rent the runway | KlassyKinks.com

The real reason I went to Chicago in the first place was to attend my friend Hugh’s wedding! We lived in the same dorm/house in college and had numerous convos about faith and family that really helped shape me. Hugh and his wife, Denise (ah!), executed an absolutely beautiful wedding that was super Pinterest worthy – from the indoor/outdoor combination, to the simple and elegant tablescapes, to the meshing of Southern and Chinese cultures – it was just lovely!

Hugh and Denise | KlassyKinks.com

Why I Love This Look: Since the wedding was a black tie optional affair, I took the opportunity to use Rent the Runway to find a gown. In case you don’t know, Rent the Runway is a platform that allows you to rent designer clothes for 4-8 days, at a fraction of the price – because you know you’re probably not going to wear a ball gown again! Even though I’m all anti-color now, I decided to channel spring and narrowed down my options to the ones below.

I ultimately went with a pink/lilac dress that had sexy cutouts, by Mignon Fashions, and when I tried on the dress at Rent the Runway’s Chicago store (don’t worry, you can get rentals shipped too), I absolutely loved the way it hugged my curves. Once my makeup and hair were done, I looked (and felt!) spectacular! Just enough glam to get compliments at the wedding, but not over the top (like sequins) that might have taken away from the bride. I rented the dress for just $75 PLUS 20% off for my first order – you can get $20 off your order too by using my referral code!

In case you really like this particular designer, here are a few more dresses from Mignon that are the perfect balance of sexy and sophisticated:

Hairstyle of choice: Elevated roll, tuck, and pin (video coming later this week)

So those are three very different looks from my weekend in Chicago, and though I really enjoyed catching up with a lot of college friends and exploring a new city, it is definitely back to the grind for me!

What was your favorite look from my week in Chicago?

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  1. I like every outfit you wore to the windy city. The casual look you glam it up. The monochrome look was sexy and chic. The wedding outfit speaks for itself and you choose the perfect gown to wear. My favorite would have to be all 3.????????????????????????

  2. Welp, I like ’em all for different reasons. Purple used to be my favorite color (still a close second) so the lilac dress has my attention. The cut is gorgeous. But I would say I’m loving the lunch date outfit. A simple tee with jeans, cute heels topped off with hat… so me!