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Stripes on Oak Street


Striped shirt, pocket scarf (under $100! This would make the best gift! There’s also a matching beanie!) shoes, and purse from Kate Spade on Oak Street // Levi’s 721 Black Skinny Jeans (also love this J.Brand version!) // MAC matte lipstick in “Diva”  // Hair curled with Beachwaver curling iron 

There are so many areas of Chicago that really come alive this time of year! One of my all-time favorite places is Oak Street in the Gold Coast. It’s a street near and dear to my heart–I used to live just a few blocks away, not to mention, I got engaged one street over!

Oak Street is one of the most well-known shopping streets in the city–it has the cream of the crop of luxury shops, but also lot’s of great everyday brands, restaurants, and salons, too! They’ve got something for everybody, and this time of year, it’s extra magical! Window shopping on and around Oak Street with a cup of hot cocoa is a winter activity that really can’t be beat! Here are some of my favorite spots to shop, eat, and stay on and around Oak Street!

Kate Spade

I hadn’t been into Kate Spade in ages, as I’ve moved further and further west as the years have gone on! They have so many adorable winter items–one of my favorites being this black and white striped scarf with POCKETS! (YASSS.)

You know me–I can never get enough stripes, so layering it over a striped tee was really a no-brainer. I love how thick and structured this version is, which makes it the perfect tee for winter! Also, can we talk about these shoes!? I squealed a little when I saw them on the shelf! They’re the perfect holiday shoe and they make any outfit so much fun. (Even, ahem, a t-shirt and jeans.)


Vince makes the most magical sweaters, so popping in here (especially in the cold!) is always a no-brainer. They have a lot of great classic staples that are amazing quality.


A store I can never resist popping into whenever I pass by! This summer they also added a monograming station. They do it on the spot, which is so much fun to watch! (This is also where I got my favorite ever Transport tote, which you can see styled here!)

Barney’s & Fred’s at Barney’s

Perusing Barney’s and ending at the top floor at their restaurant, Fred’s, is always such a fun weekend activity. Stop in for lunch, dinner, or a cocktail. The vibe is very fun and swanky–it makes me feel like a fancy lady who lunches ;-P

Le Colonial

One of my favorite restaurants in Chicago! Neal and I went on an impromptu date here when we first started dating and I have the best memories of our experience here. It’s Vietnamese-French fusion and is so delicious. The vibe is dark and romantic–I can’t think of a better date spot. (P.S. speaking of dates–here are 36 questions to ask on your next one.)

The Public Hotel 

I love love the Public Hotel. If you’re visiting Chicago, you must stay here! It’s right in the heart of the Gold Coast and they have the most beautiful hotel rooms, the most gorgeous lobby, and their bar/restaurant, the Pump Room, is one of my all time favorites! (My best friend, Courtney, also got engaged there!)

In other news, I leave for Oregon tomorrow! I can’t wait to meet my new niece, Ashlynn! (If you missed the news, I spilled the beans about becoming an aunt again in Friday’s post!) I should probably start packing now, hm? (If you also have to pack to head home for the holidays, you’ll want to see my tips for packing in a carry-on here!)

(You guys, she’s the first baby in our family to LOOK LIKE US! My nephews looked so much like their dad when they were born, and it’s so sweet that she looks so much like her mama and our whole side of the family this time!) Looks like we’re in for some crazy weather though, so fingers crossed that I make it home on time to see her tomorrow night. Send good travel vibes!

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Have a wonderful Monday and STAY WARM!!

Thank you to Oak Street Council for partnering on this post! Photos by Iron & Honey