Weekend Notes
Happy Friday, Gang! I’m headed to Chicago this weekend to visit my aunt, and I’m spending a day on Michigan Avenue while I’m there. I lived in Chicago in my early twenties, and I have such fond memories of the city, so packing for this trip felt a little like getting dressed for an old friend. Below are my weekend-in-Chicago outfits — one for each part of the trip — along with the skincare I count on when I travel.
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 gingham 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
I LOVE this outfit. A collarless black blazer over a striped boatneck tee is Classic Style at its easiest, and the washed black barrel jeans keep it feeling current — both are Madewell, so both are part of the sale. I’ll wear the jacket, but I wanted you to see the base underneath — 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.
And then there’s the bee. I pulled out my collection of Bee Brooches from Joan Rivers for this trip. My mom got me hooked on Joan years ago, and Joan had this fascinating story about bees and how they were the unlikely hero — their bodies too round, their wings too short, and yet they make it work.
- 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 month. 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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