What to Wear in Chicago in Spring

by Julie Marshall

$200

15 Minutes

Easy

Are you wondering what to wear in Chicago in Spring?

Do you live in Chicago and want to zhuzh up your looks for Spring?

Or are you considering going to Chicago for a visit and want to know what to bring?

Well lovely readers, I just returned from a two-week visit to Chicago and I thought it might be helpful to show you what I wore.

I had many special occasions to attend and casual visits with friends and family. I had lunches, dinners, teas, a bridal shower, Easter egg hunts, and more! Read along with me and see how I put together many looks from relatively few pieces.

I know you might think that since I live for seven months of the year in Chicago, I already have many appropriate clothes there. The truth of the matter is my favorite, cutest pieces are with me in California. Thus, I needed to bring home a suitcase full of clothes and accessories to be ready for my schedule.

In this post...

How to Determine What to Wear in Chicago in Spring

Whenever I go on a trip, the first thing I do is determine what events are on my itinerary. The second thing I do is look at the likely weather and temperature ranges. Of course, the weather could be unseasonably warm or cool, but I use the predicted weather as a starting point.

For instance, in trying to determine what t wear in Chicago in Spring I learned the average temperature ranges are as follows:

March 26 (low) to 42 (high)

April 36 (low) to 51 (high)

May 46 (low) to 64 (high).

My trip was from April 6-20. During that time the temperature actually ranged from 39 to 80! Oh my! Yes, Spring weather in Chicago can be surprisingly varied! But, I was able to dress around all these weather patterns with a bit of strategic planning.

Travel Looks (What to Wear in Chicago in Spring)

Pro-tip: For travel looks I try to wear my bulkiest pieces on the plane so I don’t have to use up suitcase real estate. I also make sure to wear very comfortable shoes to walk through airports.

what to wear in chicago in spring, Here is a great outfit to wear on a cold Spring day in Chicago I paired a turquoise wool coat with a turquoise v neck cashmere sweater I wore jeans off black gym shoes and a turqoise foulard bandana at my neck

Here is a great outfit to wear on a cold Spring day in Chicago. I paired a turquoise wool coat with a turquoise v-neck cashmere sweater. I wore jeans, off-black gym shoes and a turqoise foulard bandana at my neck.

First Travel Look (Outfit Number One) for What to Wear in Chicago in Spring

I wore this turquoise wool coat and would suggest you bring a wool coat or lined trench coat as the weather really does change a great deal in Chicago springtime. I chose this brightly colored coat because I wanted to look spring-like even if the temperature was cold. Pro-tip: Wearing bright colors, in your accessories and even some clothing pieces will go a long way toward making you feel pretty and confident in your travel wardrobe. (My coat is from winter, but here are a few similar options: here, here, and here).

I paired the wool coat with a turquoise V-neck sweater and print scarf. Pro-tip: Outfits definitely look more expensive when you coordinate the color of your top with your third piece (sweater, blazer, coat, etc.).

Here is a close-up of my turquoise v-neck sweater and my bandana.

I wore vintage wash J-Crew jeans as they are very comfortable for traveling and I knew I would wear them with other outfits on my trip. The small bandana helps accessorize the look and fills in the neckline.

what to wear in chicago in spring, This is my second travel day look I paired a pink boyfriend cardigan with a J McLaughlin floral scarf medium wash straight leg jeans and tan suede booties

This is my second travel day look. I paired a pink boyfriend cardigan with a J McLaughlin floral scarf, medium-wash straight leg jeans and tan suede booties

Second Travel Look (Outfit Number Two)

I love this second look as it was what I wore back on the plane to California. I frequently find planes to be cold and therefore I prefer to wear warm pieces. This J McLaughlin boyfriend sweater works well with these straight-leg medium-wash jeans. I accessorized it with a pretty spring-colored J McLaughlin scarf (last year’s but similar, here). Pro-tip: I love the scarves, belts, and purses at J McLaughlin as they are always high quality, classic in their styling, and frequently colorful.

This is my second travel day look. I paired a pink boyfriend cardigan with a J McLaughlin floral scarf, medium-wash straight leg jeans and tan suede booties

I am actually wearing a v-neck white tee from Lands End under this cardigan so that if I got hot upon arrival in Palm Springs, I could remove the cardigan and still look cute! Pro-tip: I am a big fan of v-neck tops as they serve to elongate my neck and make it look less wrinkled. Also showing a bit of my neck and my upper chest is slimming compared to crew neck tops which tend to emphasize my bust.

what to wear in chicago in spring, What to Wear in Chicago in Spring This cute pink cashmere boyfriend sweater with a pretty floral scarf and medium wash straight leg jeans

What to Wear in Chicago in Spring? This cute pink cashmere boyfriend sweater with a pretty floral scarf and medium wash straight leg jeans.

Cold Weather Spring Look (Outfit Number Three)

I wore this look to lunch with my friend, Julie. It was a bitterly cold, windy, but very sunny day! The turquoise coat worked great with the cashmere sweater and the tan wide-legged pants made for a warm, stylish look.

what to wear in chicago in spring, this is a turquoise wool coat over a similarly hued cashmere sweater My trousers are wide leg tan ones and my booties are tan suede My bag is tan and quilted

this is a turquoise wool coat over a similarly-hued cashmere sweater. My trousers are wide-leg tan ones and my booties are tan suede. My bag is tan and quilted.

I added comfy tan suede booties and the same bandana as in outfit number one. My tan purse is such a great value! It looks like a much more expensive bag and the neutral color will make it a great piece to have.

this is a turquoise wool coat over a similarly-hued cashmere sweater. My trousers are wide-leg tan ones and my booties are tan suede. My bag is tan and quilted.

this is a turquoise wool coat over a similarly-hued cashmere sweater. My trousers are wide-leg tan ones and my booties are tan suede. This is a close-up.

Travel Pajamas (Outfit Number Four)

what to wear in chicago in spring, Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over the top has a notched collar

Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over. the top has a notched collar.

I’m not sure that pajamas truly count as an outfit, but when you travel, it’s nice to have cute pajamas that are decent enough to wear with guests. For four of my nights in Chicago, I hosted my son’s soon-to-be family as I was having a bridal shower for Jake and his lovely fiancee, Rachel.

Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over. the top has a notched collar. The bottoms have a curved hem.

These darling Soma champagne glass print pajamas are very comfy and easy to wear. I usually wear a Soma nightshirt, but this notched collar top doesn’t need a robe to look appropriate. By the way, Soma sleepwear washes well and I just hang them up right out of the dryer without any problem. The pajamas are 93% rayon and a bit of spandex so they hold their shape well. The print top is apparently sold out, but here is another solid-colored top that will coordinate nicely. And it’s on sale!

Terrific Soma pajama top and shortie bottoms with a darling champagne glass print all over. the top has a notched collar. The bottoms have a curved hem. Here is a close-up.

Special Occasion Outfits (for What to Wear in Chicago in Spring)

Bridal Shower Look (Outfit Number Five)

what to wear in chicago in spring, This pink cashmere boyfriend sweater is worn over white pointe knit pants and nude pumps I added a pearl necklace bracelet and a gold watch

This pink cashmere boyfriend sweater is worn over white pointe knit pants and nude pumps. I added a pearl necklace, bracelet and a gold watch.

This is what I wore to the bridal shower I gave (along with my sister-in-law Sheila) at Exmoor Country Club in Highland Park, Illinois. This pink cashmere boyfriend sweater (M) was perfect with my nude quilted bag (terrific buy!) and nude pumps. The white pointe pants fit so comfortably (6).

This pink cashmere boyfriend sweater is worn over white pointe knit pants and nude pumps. I added a pearl necklace, bracelet and a gold watch. On my neck I also layered a gold chain necklace.

I wore a gold watch, a pearl bracelet, and diamond stud earrings. I added a long strand of pearls from Mr. G.Q. and a gold chain necklace with a central pearl.

what to wear in chicago in spring, Here is my soon to be daughter in law at her bridal shower wearing a sweet white ruffled dress and fabulous white pumps that have white chiffon bows at their backs

Here is my soon-to-be-daughter-in-law at her bridal shower wearing a sweet white ruffled dress and fabulous white pumps that have white chiffon bows at their backs.

Here’s a photo of my terrific daughter-in-law-to-be, Rachel. Don’t you love her sweet white dress and gorgeous white pumps with beautiful chiffon bows on the heels?

Here is my son looking toward the camera and my Rachel looking at Jake.

Here is the lovely bridal couple with my son Jake facing the camera while Rachel is looking at him.

Here the couple is trying on matching his and her aprons!

Here they are trying on matching his and her aprons! I found these on-line and had to get them.

Here is my son flanked by me and his former babysitter, now very close friend, Irena.

Here Jake is flanked by me and his former babysitter, Irena. She’s been a member of our family for 29 years!

This is a photo of one of the shower flower arrangements as well as one of the teapot-shaped sugar cookie favors.

These delicious cookies were made by Alliance Bakery in Wicker Park and were in the shape of teapots. The shower was a high tea party. Aren’t the flowers lovely? They were done by Eileen at Lake Forest Flowers.

A darling tote for Rachel with the words "Bride vibes" on the front!

I found this bag several months ago and had to get it for Rachel! Mr. G.Q. are so excited to have her join our family this July 8th!

Easter Dress (Outfit Number Six) of What to Wear in Chicago in Spring

what to wear in chicago in spring, Me in my royal blue floral Maggy London knee length dress and white linen blazer My sandals are light cream ankle straps and my bag is a wicker and leather one from J McLaughlin

Me in my royal blue floral Maggy London knee-length dress and white linen blazer. My sandals are light cream ankle straps and my bag is a wicker and leather one from J McLaughlin.

For Easter (it was 75 degrees!) I wore this pretty floral Maggie London dress. Mine is sold out, but here are three more from Maggie London (here, here, and here). I added a J Crew factory white linen blazer and cream Ann Taylor sandals. I love the ankle strap and pretty heel to these so much that I ordered them in black for my son’s black and white wedding. My bag is a classic J. McLaughlin wicker one with brown leather trim. J McLaughlin has such cute bags!

Going to Lunch Look (Outfit Number Seven) Of What to Wear in Chicago in Spring

what to wear in chicago in spring, A darling pink ruffled sleeve top by Avara worn over black cropped pants and black pumps My purse is hot pink and also from Avara

A darling pink ruffled sleeve top by Avara worn over black cropped pants and black pumps. My purse is hot pink and also from Avara.

I wore this darling Avara pink ruffled sleeve top with black cropped pants and black D’orsay pumps to lunch with my friend Georgie. We went to Summer House Santa Monica in Chicago. The best Spring accessory was this darling Avara pink bag that is so “Jackie O”, don’t you think? It is only $68!!! You need this if you love pink as much as I do.

Dinner Look (Outfit Number Eight) of What to Wear in Chicago in Spring

what to wear in chicago in spring, I m wearing a black ruffled strapless top from Anthropologie over black cropped pants and black pumps with a black clutch

I'm wearing a black ruffled strapless top from Anthropologie over black cropped pants and black pumps with a black clutch.

This is what I wore to dinner when I took much of my family and Jake’s new family out to dinner at Tocco’s restaurant in Winnetka, Illinois. I love this black ruffled top from Anthropologie. I paired it with black cropped pants, a black clutch (similar, here), and black pumps.

Here is a photo of both much of Jake's family and Rachel's all out together for dinner.

Above is a photo taken at Tocco’s restaurant. We had such a fun time. The weather was perfect! I didn’t even need a wrap at 10:00 P.M.!

Conclusion to What to Wear in Chicago in Spring

I hope you enjoyed seeing what I wore in Chicago during my Spring extravaganza stay! It was a trip filled with events and the outfits I brought worked well together. The weather is always fluctuant in Chicago springtime so you should bring layers such as cashmere sweaters, scarves, a fun wool coat, etc. Try to pack the brighter colors of springtime even if the items are made of more wintery fabrics. Let me know if you have any questions or suggestions about things you would bring to wear in Chicago in Spring.

Happy last week of April!

XO,

Dr. Julie

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