November 29, 2023
Through much of the time that I was searching for these items, it was snowing in Chicago. It wasn’t actually landing on the ground, which seems like an oxymoron, but from the 24th floor, we can see snow that doesn’t survive its final descent!
I love big snow drifts, so this wasn’t ideal. But we also have to be able to get out and about, so I’d best just be quiet, eh?
today’s photographs are all of Chicago…

Image – Barry Butler
if you like photographs of Chicago, look for Barry Butler on Instagram!
For today’s outfits, I was thinking about those early days of snow, when it’s not really bitter cold, but you still need some kind of boots, as well as a warmer jacket or coat, and a scarf!
To make these outfits easy, I started with a solid column of color; if you’re going to be wearing your coat the entire time you’re out, you don’t need to wear anything complicated under it, right?
Cashmere sweater – J.Crew; labradorite earrings – Panacea; corduroy jeans – J.Crew; deep olive coat – L.L.Bean; scarf – Barbour; boots – Blondo
If you have a wardrobe that includes 2 neutrals, this is an easy way to dress! All but 1 of these outfits includes two neutrals…
Forest moss cotton turtleneck – Lands’ End; burgundy earrings – Kendra Scott; knit cords – Lands’ End; down coat – Lands’ End; scarf – The Met Store; boots – Naot
If you’re going to be in Chicago and are able to visit “The Bean,” you might want to send me a note to see if I’m free for coffee or lunch; I live about 4 blocks from here!
Photo – Lydia Schrandt
If the temperature isn’t going to get too close to freezing, you can wear a cozy shirt jacket – they’re EVERYWHERE this year. But they are classic…
Rich coffee tee – Lands’ End; earrings – Olivia Le Adalena; corduroy pants – Lands’ End; pile shirt jacket – Thread & Supply; patched plaid wrap – Echo; boots – Sorel
If the weather might turn sloppy, make sure you have good boots, with waterproof soles!
Camel cashmere sweater – J.Crew; mixed metal earrings – Kendra Scott; inlay wool scarf – Echo; grey coat – L.L.Bean; twig corduroy pants – L.L.Bean; boots – Trotters
“The El” might not feel festive for you, but if you’ve been standing on a platform (in the wind!) for 20 minutes, this image might look like a gift from Santa!
Image – Secret Chicago
There’s one in every crowd – for those of us who love black, why NOT claim that silver is your 2nd neutral? This would be ideal for an event that keeps you near open doors, like caroling just inside the mall entrance…
Cashmere sweater – J.Crew; earrings – Bloomingdale’s; silver vest – J.Crew; corduroy pants – J.Crew; silver scarf – Tasha; boots – Madewell
Maybe you have one “cool” neutral and one “warm” one… Why not? Everybody is not best served by one type of color palette:
Charcoal turtleneck – Lands’ End; agate earrings – Banana Republic; charcoal pants – Lands’ End; hickory wool coat – L.L.Bean; scarf – La Fiorentina; boots – Eileen Fisher
I have walked past this at least a thousand times – seriously… it’s a Michigan Avenue landmark, and if you’ve worked in retail in that area, you’ve enjoyed this view…
Image – Chris Valera
As much as we struggle with cold and traffic, Chicago is very beautiful, all year ’round.
love,
Janice
p.s. Ten years ago, I was thinking about packing in black and white. It stands the test of time!
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Love the first and last photos. Oh my. And that camel and gray. Also the navy and olive. You’d think, as much as I truly like the camel and gray – or camel and black – that I would be able to manage a wardrobe, or at least a capsule wardrobe in those colors. But I never have. Something to think about. Over more coffee.
The charcoal and hickory colour combination is gorgeous as are the photos of your wonderful city! I’ve only been in your airport, changing planes, but I’ve mused that Janice and her Belovedest might be there too, on their way to Paris or for a quick trip someplace fun.
So far in my section of Eastern Canada we only have an inch of snow on the ground but this cold weather tells me it’s the base for what’s to come.
I, who have been shoveling snow for days, live in a thick coat and warm boots.
These are all such beautiful colors, I especially like the first two.
I was last in Chicago in 2008, this exact time of the year, with my daughter. The Saturday was like a spring day as coatless, we did a trip on the Chicago river, and did silly poses at the bean. The next day, Sunday, as we shopped Miracle Mile, the snow came down. I was snug in my long faux fur coat. My daughter ‘s wool coat got wetter and wetter the more that fell (and shrunk so badly that she was never able to wear it again). The snow settled. The views were stunning – just like those you have posted today! So…..thanks for the memories…….and before I close, let me just tell you that I was so impressed that on that snowy Sunday evening so many years ago, the airport (the one that sends and receives passengers throughout the US) transformed itself into a hostelry for those Americans who were stranded at the airport, whilst our international flight in all that snow took off on time from the other airport. I was beyond impressed and always intended to return to Chicago, alas not to be as I can’t walk these days. Perhaps my daughter will return one day. I have so many happy memories, and thank you again for the stunning photo’s
I’m in a suburb of Chicago, just north. November can vary tremendously; you were lucky! My daughter was born on November 28th, 30 years ago. When we came home from the hospital (her first experience of outdoors) she scrunched up her little face in pain and screamed. It was 20 degrees f with snow on the ground.
We WERE lucky! I think the Saturday was probably 30 November, making the Monday December 1st. We ran away to Chicago for a week after her father died unexpectedly.
I love Chicago! It’s probably my favorite city in the US. Thanks for the pictures.
I’m planning a trip to New York in January, so your ideas are on point for me right now. Thank you for all your posts.
Barrys photo is posted to my facebook for everyone to enjoy! Stay Warm!
I will definitely let you know the next time I am in Chicago….it was so nice there the 2 times that I have been. In Ontario, I am wearing my ‘puffer’ coat and short boots, and have yet to break out my parka and snow boots. However, the wind is so cold that I might have to soon, especially while waiting for the bus. These outfits are perfect for this weather….except maybe the shirt jacket.
Of course the navy + olive makes my heart sing, but the black and silver would be amazing on the right person!
Janice,
I’ve only ever been in the Chicago airport, so these cityscapes were a treat, thank you !
A warm and a cool palette — hmmm, that has been my recent struggle. I have light, warm and muted coloring, so even navy blue seems to overpower me, and yet I want an option in the blue family that works with my personal coloring. One Pinterest site suggested using teal for navy, but where to buy matching teal clothing, especially pants ? I have decided on medium dark wash denim, but the very fact that it’s denim immediately puts it into a lower level of formality of fabric than a navy garment. I know that denim has become ubiquitous as a fabric to be worn on most occasions, but it does not feel that way to me ( I’m old school ) . Having just all warm colored clothes becomes boring after a while and that is why I want to integrate some warmish blues into my wardrobe.
I can understand your dilemma. I’m a soft summer so navy and grey are my neutrals. For some years now, I have been steering a path away from dark navy. I look for mid-tones – light navy, French navy, mid grey-blues, teal blue, Prussian blue, Petrol blue, Airforce blue, Marine blue, Slate-blue. Denim need not just be a fabric. Try Lyocell or linen as a smarter option. Look for those colours in other fabrics. I wear cotton twill, linen, corduroy, velvet, suede, faux suede etc. I look for blue-grey or greyed blue colours. Teal can be green or blue. I find that you don’t have to match. Once you steer a course into mid-tones, it is about blending the tones in an outfit. Hope that helps.
Talbots has a lot of teal items available this season: https://www.talbots.com/search?q=Teal&start=0&sz=54
It’s not always easy to find, so I tend to stock up when I find it’s “in”. I got some nice corduroy pants and three tops. They are having a 30% off sale now so sizes may be limited.
I usually need a hat in Chicago! It makes all the difference in how far I walk my dog.
I just love the black and silver!!! So striking and so not me but so amazing on the right person as Sally says.
They don’t call it the “Windy City” for nothing. The wind off lake Michigan funneled between tall buildings, brrr. I think it’s always cold in Chicago. We used to take a train to Chicago and stay downtown between Christmas and New Years. Beautiful. My favorite season to visit is spring. Michigan Avenue is alive with colorful planters.
I did something similar recently to go see A Christmas Carol, my friend was acting in it. I wore a navy sweater and navy ponte pants with a plaid ruana over the top (navy, brown, cream) and no boots as we aren’t snowy in the PNW. I just wore navy dress shoes. I have never been to Chicago. Maybe someday!
I perked up at your comment about wearing cool and warm neutrals together. I have always wanted to wear camel, but look nasty in it. Recently I discovered that very light camel works on me, for some reason, so now I wear it with black and navy and grey, all of which have been in my wardrobe for ages. But not only that, other warm colors seem to work too, like deep yellow, dark brown and orange! Yipes! I have the pale skin, blue eyes and grey hair of a “winter” person. The icy pale colors that are supposed to work, and USED to work for me do not anymore. Can you explain this phenomenon?
I can’t possibly explain that! I’ve never really been sold on the “seasons” color system because it never looked quite right to me. I had my colors done twice, and got two ENTIRELY different results, so I think there’s a significant element of flexibility in choosing colors. Wear what you love, and what you feel makes you (more) beautiful, and let the systems take care of themselves!
hugs,
Janice
I love the colours of the Barry Butler (1st photo) and the Chris Valera (4th photo). I love wearing lilac, pink and light blue in winter set against charcoal grey. Parts of the UK have had a dusting of snow today too. As for the wardrobes anything silver is my choice but I would create capsules with burgundy, navy or teal with lots of velvet and faux fur.
I love those colours too. Greetings from the Isle of Wight.
Love the combo of charcoal and hickory.
I bought that maroon down coat with the hood this past weekend in that color – so cozy! And such a great price. I am excited to wear it on the plane from Arizona to Seattle for Christmas.
I love the silver and black.
We had a few flakes of snow here on the Isle of Wight, normally one of the mildest parts of Britain. This passes for excitement here!
Oh, yes. I’m a bit further north of you. It only has to be a light covering and you’d think by the reaction in Southern England, that it is a snow drift! We have had deep snow but we are more likely to get bad frosts though where the frost is so thick that it does look like snow. One of the coldest places in England is in south Oxfordshire. It recorded a night temperature of -7 on 25 November. Could get colder still.
I lived in the Cotswolds for a while. I don’t miss the winters there!
I love the silver and black as it’s so me. I am sulking and stamping my feet though as I can’t buy the earrings due to cost.
Could you PLEASE do a “Start with a Photograph” series with palettes and have that first image from Barry Butler (Sears Tower against purple clouds with dark trees and lake) as the first subject? And many of the other photos in this post would be good subjects as well. I noticed that one of the prettiest Echo scarf palettes was based on a photograph with lots of golden street lights, so there’s definitely precedent for this!
I love that idea. I’d also pick the first image.
Love the pictures and Chicago. I will certainly let you know if I’m ever near “the Bean”. As a child we would take the train to Chicago (through Kankakee). We would be all dressed up, walk around and view the window displays, then have lunch in The Tea Room! Of course we visited Santa and then caught the train back to Lafayette IN. What a day it was. All my children worked in Chicago after college but all returned to TX. WE still have cousins and nieces and nephews there so we do get back. Go Cubbies! The last time was for a wedding in January 2020. My hubby couldn’t believe anyone would marry in January in Chicago and he was raised there. I borrowed my mom’s long wool coat and changed from waterproof/slip-proof boots to kitten heels as did most of the ladies.
I was last visiting family in Chicago the summer after covid, and it was so hot, I almost wished I were home in California! Winter in Chicago looks beautiful and completely foreign to me!
We only have seasons of very hot, and then freezing. Autumn and Spring are foreign concepts…
hugs,
Janice
Oh come on—spring sometimes lasts up to 36 hours! It’s true sometimes it’s only four.