Fall Shoe Staples

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Are you a shoes or bag girl? I think in my core I’m a bag girl, but I do love my shoes! I sadly just don’t get to wear a ton of them in Chicago once the weather turns colder. Rain, sleet, snow and dirty Chicago streets don’t equate to pulling out the designer shoes unfortunately. But, I have found that there are some styles I consistently reach for every year for Fall that I get a ton of wear in before the colder temps set in and I’ll tell you why!

SAM EDELMAN LORRAINE BIT LOAFER

I first purchased this shoe in 2017 and have been obsessed ever since. I own them in silver, black, white and am looking to get these soon! They are the perfect shoe to run around in and I wear them most often to work. They are so comfortable and add elegance and polish to any look from ripped jeans and sweater to slacks and a button down if you work in corporate. They come in every color imaginable and different materials from suede, leather and patent leather and crocodile (faux). I’m very true to size in Sam Edelman and go with my normal size of 7 - they do stretch out a bit over time, but this only makes them more comfortable and shouldn’t impact sizing. I also get asked a lot if they are the Gucci pair - such a great dupe!

BLOCK HEEL BROWN BOOTIES

For the last few years I’ve been on the search for a pair of brown block heel booties that didn’t break the bank. Unfortunately, two winters ago I was wearing a pair and running to catch the bus (like really running) and the seam of the bootie completely split open when I fell on some ice (as you can imagine IT WAS A DAY). Since then I hadn’t been able to find a pair that weren’t an investment that I loved. While browsing some sites I came across these. I didn’t want true cognac, the heel height had to be right and they needed to be affordable. Well they came in last week and I love them! They are comfortable (took about two days to break in the stiffness) and I love the added height - and they’re 37% off!

STEVE MADDEN GEORGETTE OVER THE KNEE BOOTS

I’m sure y’all are familiar with this style as they’ve been all the range the last few years. I first ordered a pair that had a taller heel and since I’m somewhat tall and long legged I was just getting stripper vibes every time I wore them, which for me was not the goal. I then discovered the Georgette style from Steve Madden and love them! I have them in black and a taupe / grey color and they are easily one of my most worn shoes in Fall and Winter. Pair with skinny jeans, leggings, a long midi dress, skirt and sweater - the options are endless. These are tight enough to stay up on your leg, comfortable and the colors are great.

PERFECT COMFORTABLE PUMPS

I love wearing heels, but not all heels are created equal. The majority of the amazing ones are very uncomfortable and the comfortable ones aren’t the most exciting usually. When I was working in investment banking, I was wearing heels almost everyday and found my go-to pair that are stylish and comfortable. The Sam Edelman Hazel Pump. They come in a ton of colors, suede or leather, are the perfect heel height and very comfortable! I love the suede as they are a bit more formal and great for Fall and Winter, but I own a nude pair in leather and love them too! They come in a leopard brahma that I will be buying myself!

CASUAL SNEAKERS

In today’s trend world, it seems sneakers are here to stay. I’ve been a more athleisure / Nike girl when it comes to sneakers and I wasn’t loving the Golden Goose dirty sneaker vibe that everyone was into. I couldn’t justify spending THAT much on sneakers that looked they had been in the back of your closet for 10 years… so I opted for some dupes that weren’t as distressed and they did not disappoint! I ordered these from SHEIN to give the trend a try and really like them! I pair mine with jeans and even dresses for a more casual look. I’ve added some other styles below, but if you order from SHEIN I would go up a size!

SNAKE SKIN

Leopard is very in this season and so is snake skin! Really any animal print, but one I am loving with neutrals is snake skin. From booties, to slides to pumps, I look the way it adds some edge to your look that is a bit more understated than leopard. I got these Sam Edelman booties last Christmas and love them! Paired with jeans and even shorts if it’s still warm where you are, they are a low heel and pretty comfortable - they are a thick material so breaking in takes a bit. One of my favorite pairs of shoes were a gift from Kollin and he totally surprised me with - you guessed it - snake skin! They are an older style, but are similar to these!

Mules

Similar to the loafers at the top of the post, the mule loafer style was all the rage when Gucci made them in every color, with fur, and multiple designs. While they won’t transition you into winter, they are an easy, on-the-go style that you can wear throughout the Fall season. I love this pair, but have added some cheaper options below too!

BLACK BOOTIES

Always a classic and always chic, black booties will be a closet staple for years for come. I prefer a black heel for comfort, but love a stiletto black bootie too! My favorite pair are shocker, Sam Edeleman Hilty Pointed Toe Bootie, but I’ve linked some other amazing ones too! Pair these wth a pair of skinny black denim or even leather leggings for a date night and wear more casually with a cute sweater and skirt during the day.

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Date Night Spots in Chicago

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SHOP THE LOOK

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If there is one thing that Kollin and I love - it is date night. And not just like “hey, let’s grab something quick,” but a more get dressed up, make a night of it, romantic date night. We’ve lost sight of doing these during wedding planning, but now that the wedding is over we are full steam ahead on getting date nights back on the calendar! I’ve rounded up some of our favorite places (and why) and some that we are hoping to try soon. They range in price, but I would say the majority you could keep the check relatively low without drinks (that’s where they get you in Chi). As a heads up you’ll see a lot of Italian, New Wave American and some Michelin Star Restaurants, but don’t let the Michelin rating scare you from going - many have several affordable options and the experience is something you’ll never forget!

Riccardo Trattoria

  • $$-$$$ - Lincoln Park

  • Established in 1943 by a family from Milan, this was our go-to nice Italian restaurant for a long time. We’ve been on date night, brought family in and love the intimate, family-oriented vibe. We love the meatballs and calamari to start, gnocchi and the ravioli di vitella alla massaia (veal and pork filled ravioli tossed with meat sauce, Porcini and a touch of cream).

Eataly

  • $-$$$ - River North

  • What we love about Eataly is that it is what you make it. If you’re in the mood for a panini and gelato or a full three course meal - you can have either here. Designed as an Italian Market, this date night spot is perfect for roaming around and discovering amazing Italian food, drinks and more. Several sit at the counter type restaurants are inside the market and it is so fun to sit and watch as the food is prepared, learn about different Italian specialties and they often hold wine tastings and cooking classes.

Piccolo Sogno

  • $$$ - River West

  • Ok, last Italian place! But, this one is so great. We took my mom here for her birthday and it was so good! We started with a bottle of rose to share and then opted for the burrata to start, ravioli, papardelle and Kollin got the Ox tail. I would say if you’re looking for a fancy Italian night-on-the-town date night go here rather than Riccardo’s, but if you want a more quiet, intimate spot opt for Riccardo’s.

Bad Hunter

  • $$- West Loop - Vegetarian Options!

  • Packed into one of the most amazing restaurant areas in the city - W Randolph Street - this little spot is where a girlfriend and I had dinner one night to catch up. She’s a vegetarian and they had so many things to offer in that category. While I’m not a vegetarian, we usually end up sharing everything anyways and it was so delicious! We ordered: sparkling rose, burrata, butter dumplings (I could eat five plates of these and would go back to just order them), Mezze Maniche Pasta for me (it had panchetta). We loved the atmosphere here and it is perfect location wise to walk around post-dinner for drinks or dessert, especially in Summer.

The Loyalist

  • $-$$ - Near West Side

  • Part of the dual-restaurant establishment, The Smyth and The Loyalist - the later is a downstairs, casual basement-esque bar/lounge that sits below the same owner’s two-star Michelin restuarant, The Smyth. Kollin and I have yet to try The Smyth, but we frequent the Loyalist and have a somewhat controversial stance on their star of the menu: the cheeseburger. If you ask most people in Chi what the best burger in town is, the majority of them will say Au Cheval - and while they aren’t wrong in it being really really good, Kollin and I love the Loyalist burger even more. We ordered the Foie Gras Eclair, Deviled Eggs, Broiled Oysters and each got the “Loyalist” burger (yes, order your own. You will thank me later). We’ve had their special burger and it was also delicious so if you’re with more than 2 people order both and share, but do not skip out on the original!

Boka

  • $$$ - Ranch Triangle - One Michelin Star

  • Kollin and I took his brother and girlfriend here for a fancy date night and it did not disappoint! It has been awarded a Michelin star for 7 consecutive years and it isn’t hard to understand why as soon as you walk in. Very luxurious, but whimsical we were seated by a plant wall filled with paintings of what appeared to be aristocrats with animal heads. Big cushioned chairs and moody paint palettes add to the fun and eclectic vibe. We each started with a cocktail (very good!) and the ricotta dumplings (insane). I had the roasted chicken and Kollin ordered the short rib. Both were outstanding. They offer an 8-course tasting menu, but we opted to try that when we came back on our own.

Girl and the Goat

  • $$$ - West Loop

  • Located in that same amazing restaurant area of W Randolph Street, I’m a little bitter about this one… We had been wanting to go here for a long time, but every time we tried it was booked solid. Kollin and his brother stumbled in one night on a whim without a reservation and sat at the bar. Owned by Stephanie Izard, the first female winner of Top Chef, it is one of Chicago’s most popular restaurants and the food (only Kollin and his brother would know…) meets the hype. I don’t know for sure what they ordered (other than pig face (yes, literally) and “the best dessert we’ve ever had - baba au bourbon”), but the crab rangoon squash blossoms, seared scallops and the goat empanadas look tasty to me!

Cantina Laredo

  • $$ - River North

  • This is where a previous boss would take us to celebrate a big deal win or simply some team bonding over margs and I’ve loved it every time! From the fresh table-side made quac and the quesadillas and ceviche, this place is an easy, casual but still upscale for date night place! It is also in a great night-life neighborhood if you’re looking to make a night on the town happen post dinner!

Copper Fox

  • $-$$ - Streeterville

  • When Kollin and I lived in Streeterville this place became our “I don’t feel look cooking… date night!” place. It’s up there with one of my favorite burgers in the city and is located in the Marriott hotel. It was usually pretty quiet and gave that perfect close to home, but still special environment. You have to order the baked Gouda mac and cheese, #16 biscuits, and the Fox burger. Kollin and I usually split all this and ordered drinks for the perfect amount of food.

Blackbird

  • $$$ - West Loop - One Michelin Star

  • Blackbird was Kollin and I’s first Michelin experience in Chicago and it has become our favorite restaurant. We first went here on our 5 year anniversary and then he surprised me again on my 25th birthday and we went back. Each time has been so memorable. From the amazing food, exceptional service and overall experience, the attention to detail is perfect. The first time we went was for Chicago’s Restaurant Week and we did the pre-fixe menu. (This is a great way to experience some higher priced places in Chicago if you are here in Jan-Feb). The second time we visited we ordered a la carte. While the menu changes often, I have not tasted one thing that I did not LOVE here. If I have any advice on Michelin restaurants, always, always have dessert. The best desserts we’ve ever had have been at Michelin places and are so memorable - here we had a mango Popsicle with spice cake and bourbon ice cream that were out of this world.

Tanta

  • $$-$$$ - River North

  • One of the first Peruvian places we tried in the city, this was another favorite of my former boss. Filled with awesome cocktails, tons of ceviche and traditional Peruvian dishes, it is simply good food. If you aren’t into spicy I would definitely make that known as some dishes have some heat. We haven’t been back in a while because there is so many new places to try, but it is very good!

Sunda

  • $$$ - River North

  • This new-Asian spot is great for a unique date-night and the food is so good. I first went here with work peeps and then took Kollin back after I brought home left overs and he devoured them. If you go, try the crispy brussels sprout salad - I’m not a big salad girl and don’t like brussels sprouts and loved it if that tells you anything… we also got the lemon grass lollipops, long rib and a few sushi rolls. Can’t really go wrong here!

Summer House Santa Monica

  • $$ - Lincoln Park

  • A California oasis in the heart of Lincoln Park, this spot is relaxing, fresh and a great vibe. Go for a glass of rose, the crab cakes, and four cheese tortellini. I’m not into nigiri, but Kollin ordered the spicy tuna and said it was great also! It is in a super cute neighborhood so take a walk around after and see the shops and amazing houses near by.

Donkey Table Stick

  • $$- Logan Square

  • We went here the day we found out Kollin passed the bar and had the best time. A tiny place in Logan Square that seats maybe 30 people, we went for the bourbon selection, but loved everything we had. We started with a glass of rose for me and a celebratory shot of Pappy Van Winkle for Kollin and the potato latkes. I had the CDK burger for dinner and Kollin had the special which I am completely blanking on, but the scallops were a big contender too!

Cabra

  • $$ - West Loop

  • Located on the roof of the new Hoxton Hotel, this Peruvian cevicheria is the newest restaurant from Stephanie Izard (Girl and the Goat above). We came here on a double date with Kollin’s brother and girlfriend and it was so good! We ordered so much, but these are our favorites - start with a cocktail - we recommend Golden Hour or Malambo No. 5 - and then order about 4-6 small plates to share. Here’s what we loved - shrimp ceviche, crab causa, Chicharrón del Puerco, Chicken Thigh Anticucho, and the Picarones for dessert. This place has an amazing view of the city and is so gorgeous at sunset.

Duke of Perth

  • $$ - Lakeview

  • Kollin was on the hunt for good fish and chips in the city and his PT, who is British, told him about this place and how it was the only place she has found in Chicago that is relatively up to par with English fish and chips. We went one night and it was sooo good. I don’t even eat fish and was asking Kollin for more bites. You also have to order the potato soup. It’s bomb. They have a cute back courtyard with lights and music that is dreamy during summer nights.

Duck Duck Goat

  • $$$ - West Loop

  • Another Stephanie Izard restaurant, and just as delicious as the others. We came here on a double date and then again with a work event and it was delicious. I encourage you to be adventurous as this place as it has a unique menu. Just try it once! We ordered shrimp toast, wood-fired duck heart, Jiaozi (Beef short rib and bone marrow pot stickers), wood-fired ribs, beef slap noodles, the duck fried rice, and the mango coconut cloud for dessert. Needless to say, we were stuffed and it was delicious.

Roister

  • $$$ - West Loop - One Michelin Star

  • We first came here for dinner and then again the morning of Kollin’s graduation from law school for brunch. I’ll start with dinner - it was just the two of us and we were seated next to these guys who come to find out were traveling for business. As our food starting coming out they kept saying they regretted what they ordered and kept asking what our dishes were. We started chatting more and strangely enough we ended up pushing the tables together and all sharing our plates. It has been a while since we’ve been so the menu has completely changed over, but everything we ordered was outstanding.

  • When we went for brunch we had the foie toast (omg so good - Kollin is allergic to strawberries and didn’t care. He couldn’t stop eating it), the fried-chicken sandwich, the chicken and waffles and ended with the milk and cookies.

    • Side note: this restaurant is owned by the same chef of Alinea, the three-star Michelin rated (the highest accolade and only three star in Chicago) restaurant and is currently ranked #21 best restaurant in the world.

Prime and Provisions

  • $$$$ - Loop

  • When we first moved to the city, this place was our go to for a fancy steak dinner date night. The traditional steak and seafood restaurant was always delicious and always a special spot since we mostly came here for anniversaries. We both love crab cakes and this our favorite we’ve had in the city - it’s lobster and crab and massive and so good. We followed that with the lobster bisque, and usually split a steak with the mac and cheese, charred sweet corn (you have to get this), and the asparagus. For dessert, we were usually always surprised with their s’mores as a celebratory gift from the restaurant for our anniversary and it is such a cool experience. I won’t spoil it, but order it when you go! They also have a cigar menu if you are into that - which obviously Kollin very much was. There is a lounge you can sit in outside and enjoy.

XOCO

  • $-$$ - River North

  • A restaurant by Rick Bayless, a very prominent and successful chef in Chi - XOCO is a Mexican marketplace type casual spot that offers street food like great sandwiches, soups and empanadas. Kollin and I mostly came here for lunch dates during the work week and loved how delicious it was, but it didn’t break the bank. I usually ordered the Cubana or chicken tinga tacos and Kollin loves their soups. The churros are also really good!

While everything above are places that Kollin and I (or just one of us with friends) have gone, here are some of the places we want to try next that have rave reviews:

Ada Street

Monteverde

Maple & Ash

Le Colonial

Oriole

Momotaro

Alinea

Proxi

Kuma’s Corner

I could go on forever because there are sooo many places and even though we’ve lived here for four years, we feel like we’ve barely scratched the surface. We would love to hear your recommendations too! Be sure to check out my Chicago Guide for great brunch and other eatery options that I wrote a couple years ago. Thanks so much for reading and let me know of any questions you have if you’re planning a trip to Chi! xx

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Thank you to SHEIN for the gifted shorts. It is brands like yours that make The Creative Brief possible. All opinions are my own.