Weekend Notes
Happy Friday, Gang! Chicago is calling. I’m flying up this weekend to visit my aunt, with one full day reserved for Michigan Avenue (a girl has priorities). I lived there in my early twenties and have such fond memories of the city, which is why packing for this trip felt less like packing and more like getting dressed for an old friend. I’m sharing my weekend-in-Chicago outfits below — one for each part of the trip — along with the travel skincare I never leave home without.
ICYMI: Chico’s Just Dropped New Arrivals for Fall · Suede Season: The Fall Handbag Edit · Fashion Influencer Over 60: 10 Years in Front of the Camera
Key Takeaways
- Four occasions, four outfits — and one navy cashmere sweater that works twice, once as a top and once over the shoulders.
- A jacket you can take off is the smartest thing in the suitcase; both my travel and shopping looks stand on their own underneath.
- Travel skin needs hydration first — a mask, a mist and eye patches all earn their spot.
What Are the Best Weekend in Chicago Outfits for Fall?
For a fall weekend in Chicago, pack one outfit per occasion and build each around a layer you can remove: a comfortable travel look with a light jacket, a polished daytime outfit with flat shoes for walking, one dress for dinner, and an easy classic for visiting family. Keep the colors close — mine are navy, black, olive, and a little leopard — so pieces can stand in for one another if the weather changes its mind.
A quick note on the sale: three of my pieces this weekend are from Madewell — The Nolita Cutaway Blazer, the Darted Barrel Leg Jeans, and the Quilted Jacket — and the Madewell Insider Sale is on right now with 25% off.
Travel Day Outfit: Navy on Navy with a Quilted Jacket
What I’m wearing: Bare Cashmere Cellini Sweater · Ruti On The Loose Pants · Quilted Jacket (Madewell) · Suede Loafers · Burberry Tote · Delsey Luggage
I love these Ruti pants — truly love them. The barrel shape gives them some presence, and they’re comfortable enough for a full day of getting from here to there. With the navy cashmere polo on top, it’s one long line of color, and then the quilted jacket from Madewell and tan suede loafers do the talking. I’ve shown the look without the jacket, too, so you can see the base.
- Outfit formula: soft knit + easy pant in the same color + patterned jacket + loafer + roomy tote.
Michigan Avenue Shopping Outfit: Black Blazer and Stripes
What I’m wearing: The Nolita Cutaway Blazer (Madewell) · Long Sleeve Boatneck Tee · Darted Barrel Leg Jeans (Madewell) · Leopard Flat · Black Satchel Handbag · Bag Charm
The Outfit
Now this is my kind of outfit. A collarless black blazer over a striped boatneck tee is Classic Style at its easiest, and the washed black barrel jeans keep the whole thing feeling current — both are Madewell, which means both are part of the sale. I’ll be wearing the jacket, but I wanted you to see the base underneath, because the tee and jeans hold up perfectly well on their own. Flats are the only sensible choice for a day of walking, and the leopard adds a little warmth to all that black and white.
The Bee
And then there’s the bee. I pulled out my collection of Joan Rivers Bee Brooches for this trip. My mom got me hooked on Joan years ago, and if you ever watched her on QVC, you know the bee came with a story. At one point the powers that be had decided Joan was “too New York” — America, they said, would never take to her. The very next year she won a People’s Choice Award, and her husband, Edgar, marked the occasion with a diamond bee brooch from Van Cleef & Arpels. His reasoning? A bee has no business flying — the body is too round, the wings too short — and yet up it goes. You’ve done the impossible, he told her. When Joan launched her jewelry line on QVC in 1990, a crystal version of that very bee was the first piece she ever sold, and she later called it her most treasured possession. I like knowing that whole story is pinned right there on my jacket.
- Outfit formula: collarless blazer + striped tee + barrel jean + printed flat + structured bag + one brooch.
Chicago Dinner Outfit: The Sweater Dress
What I’m wearing: Lily Sweater Dress · Vivi Metallic Pump · Pastel Glass Earrings · Suede Dash Bag
One dress, and dinner is handled. This ribbed knit is a deep burgundy with a little lilac trim at the neckline, waist, and hem — a detail you don’t notice at first and then can’t stop looking at. It has sleeves, which I appreciate in a city with a breeze off the lake, and a silver pump wakes up all that rich color. The suede bag picks the burgundy right back up — if you read my fall handbag edit on suede season, you’ll recognize it.
- Outfit formula: knit midi dress + metallic shoe + tonal bag + one interesting earring.
Saturday with My Aunt: Oxford Shirt and Olive Chinos
What I’m wearing: Lightweight Oxford Shirt · Weekender Pant · Bare Cashmere Cellini Sweater · Calfhair Belt · Leopard Buckle Shoe · Black Satchel Handbag
For a day of visiting, I want to be comfortable enough to sit and talk for hours and still look like I made an effort for someone I love. A light blue oxford tucked into olive chinos does exactly that. The navy cashmere from travel day comes back, this time over my shoulders — it’s there if I need it and it finishes the outfit if I don’t. A leopard belt and a leopard shoe keep blue-and-olive from feeling too buttoned up.
- Outfit formula: oxford shirt + wide-leg chino + sweater over the shoulders + printed belt and shoe.
Beth’s Style Tip: When you pack, look for the piece that can do two jobs. My navy cashmere is a top on travel day and a layer on Saturday — one less thing in the suitcase.
My Travel Skincare
When I travel, skincare is of utmost importance to me, and hydration comes first. (I shared my travel beauty essentials earlier this year, and I wrote about what I’m swapping in my skincare routine as the weather turns just last week.)
- Summer Fridays Jet Lag Essentials Kit — I love a hydrating mask, and this kit has the whole lineup: Jet Lag Eye Patches (one pair), the Jet Lag Mask + Moisturizer in a deluxe size, a mini Jet Lag Skin Soothing Hydration Mist, and the Jet Lag Deep Hydration Serum.
- Summer Fridays Daily Exfoliating Pads — I like these, too.
- Dr. Dennis Gross Alpha Beta Universal Daily Peel Pads — but Dr. Dennis Gross has the best one-two punch. It’s a two-step AHA/BHA peel pad, dermatologist-formulated to smooth texture, refine the look of pores, and diminish visible fine lines.
- Rodan + Fields REDEFINE Regimen — I’m on week two of this routine, which softens and exfoliates to refine the look of pores, helps smooth fine lines and wrinkles, and visibly defines facial contours. And I like it. I really like it! I added the Rodan + Fields REDEFINE Intensive Renewing Serum as my last nighttime step.
- NARS Notorious Mascara — it comes in Starstruck black and Infamous brown.
Two More Things I Love Right Now
It’s sweater weather — or soon to be — and this Striped Cardigan is a great weight as we transition into fall.
I also love a quirky handbag with personality, and Kurt Geiger always delivers. The Kurt Geiger Mini Kensington Ophelia is the latest to catch my eye.
Amazon Goodies
In case you missed them, the last two Amazon posts are here: Fall Amazon Porch Finds: 10 Cozy Front Door Picks and Fall Amazon Decor Finds: 10 Finishing Touches.
Your Top Five This Week
These are the five things you’ve added to cart most this week. No hints — you’ll have to click.
Five · Four · Three · Two · One
What’s Good?
What are you reading, watching, or cooking right now? And if you know Chicago, tell me where to eat — I’d love your recommendations in the comments.
Closing Thoughts
There’s something lovely about going back to a city you knew when you were young, and about packing a suitcase for the person you’re going to see as much as for the place. I’ll be thinking of my mom when I pin on that bee, and I’m looking forward to every minute with my aunt.
Style has no expiration date — and neither do you.
Frequently Asked Questions
Layers. A light jacket or blazer over a knit or tee, a comfortable pant or jean, and flat shoes you can walk in. Add one dress for dinner and you’re covered.
A soft sweater and a relaxed pant in the same color, topped with a jacket you can remove. Finish with a loafer that slips on and off easily.
A flat with real support — a pointed flat, a loafer, or a low block heel. Save the pumps for dinner.
Lead with hydration: a mask or rich moisturizer, a mist during the day, and eye patches when you arrive. Keep exfoliating gentle until you’re settled.
Plan one outfit per occasion and keep your colors close. Then look for one or two pieces that can be worn twice in different ways.
Shop the Post
Browse my full ShopMy storefront for outfits, home, and more.
Travel Day
Friday Shopping
The Nolita Cutaway Blazer (Madewell)
Darted Barrel Leg Jeans (Madewell)
Friday Dinner
Saturday
Skincare, Beauty & More
Summer Fridays Jet Lag Essentials Kit
Summer Fridays Daily Exfoliating Pads
Dr. Dennis Gross Alpha Beta Universal Daily Peel Pads
Rodan + Fields REDEFINE Regimen
Rodan + Fields REDEFINE Intensive Renewing Serum
Kurt Geiger Mini Kensington Ophelia
Before You Go
Which of the four outfits would you wear first? Tell me in the comments.
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Eat at ‘The Girl and the Goat’ if you can get in. RPM Italian ‘The Little Goat’ which is the diner version.
Try Frontera Grill by Rick Bayless if you are looking for great Tex Mex.
A food capital city for sure!
Bon Apetit, Beth.
I really like the black blazer one the best. Have fun!
Thank you so much
for the great information.
Love the Chicago outfits! The first time I visited Chicago many years ago, I was dressed in my Palm Beach colors and many couldn’t stop staring at me! lol I now have outfits suitable for traveling out of the state of Florida! I am reading The Book of Longings by Sue Monk Kidd, thinking about the Madewell quilted jacket, and getting out my bee broach gifted to me by a student sixteen years ago.
Enjoy Chicago! One of my favorite cities. I am a frequent visitor there as younger son lives in Lincoln Park. We always stay at the lovely Talbott Hotel which provides easy access to nearby shopping. My favorites are the Bloomingdale’s on Michigan and shops on Oak! Safe travels!
I liked all of these outfits, but would be the most comfortable in the outfit for visiting with your aunt. I really loved the dinner dress and put it in my cart, but I doubt I’ll ever have a place to wear it or the money to purchase it! You have some expensive clothes, so I’ll look for similar items in my budget. But…that dress…I love!
My fave is the “Michigan Avenue Shopping Outfit” — complete with Joan’s bee pin. Hope you have a wonderful weekend with your aunt in the Windy City!
Enjoy the weekend. I hope you packed an umbrella and raincoat.
The sweater dress is so beautiful on you!
Great post with wonderful information!
Love the bee story! I used to watch Joan Rivers on QVC all the time! I knew the basic story of her bee pins, but not the full story.
Thanks for sharing that.
Have a wonderful weekend!