One of the texts I receive most often has surprisingly little to do with what someone should wear. Instead, it’s some variation of, “Where are people shopping in Chicago these days?”
And while I’m always happy to share where to find a great pair of trousers, a special vintage piece, or a gift that doesn’t feel like an afterthought, I figured it was time to expand the conversation beyond the closet.
I share quite a bit about my work here, but admittedly, not nearly as much about life outside of it. And the truth is, a lot of what inspires my perspective on style has very little to do with fashion itself. It’s the interiors of a beautiful restaurant, an unexpected color combination in a shop window, the way someone has styled a dinner table, or an afternoon spent wandering through a neighborhood with absolutely no agenda.
After 30+ of living in Chicago, I’ve developed some pretty strong opinions about where I like to spend my time. That hasn’t stopped me from trying every new place that catches my attention, of course. I’m always willing to put a favorite to the test, but there are certain places I find myself returning to again and again.
So, consider this less of a definitive Chicago guide and more of a peek into my little world. The places I take friends, the dishes I order without looking at the menu, and the shops where I inevitably find something I didn’t know I needed.
And while I may be a little biased, I’d like to think my list is fairly well researched.
First, Coffee. Always Coffee.
I am very much a creature of habit when it comes to my morning coffee, although I like to think I’ve earned the right to be particular about it.
La Colombe is my everyday stop, largely out of convenience, and it does exactly what I need it to do. I’m a half-tan, no-ice kind of girl. I realize that’s a rather specific order, but once you know what you like, why complicate things?
Now, when I want coffee to feel like a treat rather than a necessity, Sawada is hands down my favorite.
I don’t discriminate against anything on the menu, which is saying something considering how particular I can be about coffee. The consistency is what keeps me coming back. I’ve tried plenty of coffee shops around the city, and nothing has quite managed to dethrone it.
It’s also the kind of place that makes you want to linger a little longer than you intended. And if I’m being perfectly candid, I love any excuse to turn a quick coffee run into a proper outing.
Where You’ll Find Me Eating
I should probably preface this section by saying that I love food. Possibly as much as I love clothes. And while I’m always excited to try the newest restaurant in town, my favorite places tend to be the ones where I know exactly what I’m ordering before I’ve even sat down.
For the days when I need something quick but actually good, FARE has become a recent obsession. It’s my go-to for a healthy breakfast, lunch, or dinner when I don’t have the time or energy to overthink a meal. And on the weeks when cooking feels particularly ambitious, their family meal is a lifesaver. I love finding places that make eating well feel easy rather than like another task on the to-do list.
For a post-shopping glass of wine, Hugo’s is hard to beat. Their happy hour is one of my favorite examples of girl math. Fifty percent off a bottle of wine? Well, naturally, that means we can order a better bottle. It’s the perfect excuse to settle in after an afternoon of shopping, compare purchases, and convince ourselves we’ve been financially responsible.
Le Colonial is one of those places I never seem to tire of. And while I appreciate the atmosphere, I’m really there for the food. The eggplant, chicken salad, garlic noodles, and ribs are nonnegotiable. I realize that sounds like an aggressive amount of food, but I don’t believe in going somewhere you love and ordering conservatively.
When I’m craving sushi, it depends on the mood. Akirō, it’s all about the handrolls. Specifically, the scallop handroll, which might genuinely change your world. For something a little more casual, Sushi-san is an easy favorite for happy hour. And while everyone has their sushi order, I would argue that the crab crispy rice is one of the most slept-on items on the menu. Just trust me.
For a cozy dinner, Elina’s is always a good idea. There is something about a restaurant that feels intimate and a little nostalgic that makes you want to return. The rigatoni alone is reason enough to make a reservation. It’s exactly the kind of place I want to go when the weather turns cold and all I really need is a great bowl of pasta and a glass of red.
Rootstock is another favorite for a weeknight that deserves a little more attention. It strikes that rare balance of feeling relaxed and interesting at the same time. The wine is always part of the appeal, and it’s one of those spots where an ordinary Tuesday can turn into a genuinely lovely evening.
When I’m craving Chinese, Chef’s Special is the answer. I have a particular weakness for the salt and pepper fish. It’s one of those dishes I find myself thinking about days later, which is generally my benchmark for whether something deserves a place on this list.
And finally, Vaca’s Creamery for vegan ice cream. I don’t need my ice cream to be vegan, but I do need it to be delicious, and this delivers. Sometimes the best discoveries are the ones that surprise you.
I should probably stop here before this turns into an entire newsletter dedicated to what I’ve eaten recently. Although, judging by how much I had to say, perhaps that’s not the worst idea.
Now, Let’s Talk Shopping.
Recently, a dear friend and editor reached out asking where the “cool girls” shop in Chicago.
I don’t necessarily consider myself a cool girl, per se, but I do spend a considerable amount of time thinking about what makes something interesting, whether that’s a beautifully constructed jacket, a piece of vintage glassware, or a shop with a really distinct point of view.
And perhaps unsurprisingly, my favorite places tend to have one thing in common: They make you look at something familiar in a completely different way.
These are the shops I send clients to, recommend to friends, and visit myself when I need a little inspiration.
Space519
If you have an afternoon to wander and absolutely no idea what you’re looking for, this is where I’d send you.
Space519 is the perfect catch-all for something with a little personality, whether that’s a statement piece for a night out, something special for an event, or a hostess gift that doesn’t feel like an afterthought.
What I appreciate most is the curation. There’s a clear point of view behind what makes it onto the floor, and that makes shopping feel like discovery rather than endless browsing. Even when I walk in without needing anything, I inevitably find something I want to take home.
Nina
I have a particular appreciation for a great graphic tee. It’s one of those pieces that can make an otherwise simple outfit feel infinitely more interesting, provided you find the right one.
Nina has a wonderful eye for exactly that. Their collection of vintage-inspired graphics and unexpected finds feels genuinely difficult to replicate with a quick online search. And that’s part of the appeal.
A great tee should feel like something you discovered, not something everyone else is wearing. This is where I go when I want to find one with a little personality.
Posh
If you’ve ever found yourself getting disproportionately excited about a beautiful wineglass or an interesting serving dish, we will get along just fine.
I am a sucker for glassware and dishware, and Posh makes me want to reconsider my entire tablescape on a regular basis.
It’s the kind of shop where you walk in looking for one little thing and leave mentally redesigning your next dinner party. What I love is how a single unexpected piece can completely change the way you look at everything you already own.
Which, now that I think about it, is not all that different from how I approach a wardrobe.
Felt
If your closet is full of perfectly nice clothes but nothing feels particularly exciting, I’d suggest spending an afternoon at Felt.
What makes this shop special isn’t just the merchandise. It’s the people and their willingness to encourage you to try something you might not have considered on your own.
The team makes trying things on genuinely fun, and I appreciate their creativity and point of view. It’s a reminder that shopping can be playful, and that sometimes all it takes is seeing a piece styled differently to realize how much possibility already exists in your wardrobe.
Past Studies
This is my personal escape when I want to pretend I’m vintage shopping in Paris.
There’s something about vintage shopping that I find incredibly satisfying. You can’t always go in with a plan, and you certainly can’t expect to find the same thing twice. You have to be willing to look, experiment, and occasionally leave empty-handed.
Past Studies consistently has an interesting mix of designer pieces that are genuinely hard to find, vintage Levi’s, and more everyday discoveries.
It’s the kind of place that rewards curiosity. And for someone who spends so much of her professional life shopping with a very specific purpose, I find that rather refreshing.
Merz Apothecary
I could happily spend far too much time wandering through Merz.
It’s one of my longtime favorites for personal care, skincare, and those wonderfully specific products you didn’t know existed until you found them on a shelf.
I love discovering the under-the-radar brands they carry, and it’s one of my first stops when I need a gift that feels thoughtful, useful, and just a little unexpected.
There’s something rather charming about a shop that encourages you to slow down, read the labels, and discover something new. A little old-world shopping experience in a city that is constantly changing.
A Few Final Thoughts
One of the things I love most about living in Chicago is that there is always something new to discover, but the places that stay with me are rarely the ones generating the most buzz.
They’re the places with a point of view. The ones where someone has clearly thought about the details, where the experience feels personal, and where I leave feeling like I’ve discovered something worth sharing.
I suppose that’s the common thread between the restaurants, coffee shops, and boutiques I find myself drawn to. I’m far less interested in something simply being new or popular than I am in whether it feels special.
And perhaps that’s why I love this city so much. There is an endless amount to explore, but over time, you build your own little version of it. Your coffee order, your favorite table, the shop you always pop into when you’re nearby, and the dish you insist everyone try.
These are a few pieces of mine.
Now I’m curious, for my Chicago readers, what am I missing? Where are the places you return to again and again? I’m always looking for a new favorite, and I’m more than happy to put your recommendations to the test.
xx,
