January 17, 2018 - Easy Outfits, I Feel Pretty, Packing Lists, Style

Chicago Packing List and Outfits – Winter Weekend

Chicago Packing List

You know how obsessed I am with creating packing lists so it’s high time for a new one – this time it’s a Chicago packing list for a winter weekend. If you follow me on Instagram, you already know that my husband Craig, our daughter Aubrey and I took a post holiday trip to Chicago last week with one goal in mind…eating!  Therefore, we didn’t really think about the fact that we were scheduling our trip during one of the coldest times of the year to visit. Boy were our Texas acclimated bodies in store for a shock!

You ladies in cold climates already know this but let’s just say that what to wear in Chicago in winter can be summed up in one word:  LAYERS!

On the day of our arrival, the high was 9 degrees with a wind chill of -15.  Heat wave!  After checking our forecast for the week, I packed up a few of the pieces from the Winter 2017 GYPO Style Challenge to create a mini capsule wardrobe for our four day weekend in Chicago.

Although this post isn’t about what to do in Chicago, let me recommend the following: The Art Institute of Chicago, Portillo’s for Italian Roast Beef and Chicago dogs, Sky Deck (go out on the platform, I dare you!), the Lincoln Park Zoo (it’s empty on a cold day!), Second City (world class improv, one of our favorite things we did), Museum of Science and Industry (fun and interactive) and of course shopping on the Magnificent Mile.

Aubrey and me chillin’ (literally) in Chicago!

That smile is actually a look of terror!  I HATE heights, hate, hate, hate, loathe entirely. One of my 2018 goals is to feel the fear and do it anyway, so, thanks Sky Deck, mission accomplished!

The frozen tundra a.k.a. Lake Michigan.

A fun night of improv at Second City.

20 Piece Chicago Packing List – Winter Weekend

chicago packing list

This 20 piece Chicago packing list will give you plenty of dress up/dress down options that will work for everything from a walking tour of the city to dinner and drinks out. In addition to these 20 pieces, I also brought a work out outfit (wishful thinking – that didn’t happen!), two pairs of pajamas and of course, bras and undies.

Tip:  Pin this post for future reference. It’s a great packing list for any cold weather destination!


1. Tunic Sweater (any solid color)

2. Black Turtleneck Sweater

3. Gray Sweater


4. Faux Leather or Fleece Lined Leggings

5. Gray Jeans


6. Wool Top Coat

7. Black Parka


8. Leopard Ankle Boots

9. Black Rugged Boots


10. Plaid Blanket Scarf (coordinate with tunic sweater)

11. Faux Fur Scarf

12. Buffalo Plaid Scarf


13. Pom Pom Beanie

Layering Tops

14. Long Sleeved White Top

15. Long Sleeved Black Top


16. Cross Body Purse

17. Pendant Necklace

18. Earrings

19. Wool Socks

20. Leggings or Tights (for layering)

Mix and Match Outfits

Each sweater is styled two different ways for a total of six outfits – one version for comfortably (and warmly) touring the city, the other version is dressier and appropriate for going out to dinner.

Outfit #1
Parka + Black Turtleneck + Layering Top + Buffalo Plaid Scarf + Gray Jeans + Black Boots

Outfit #2
Wool Coat + Black Turtleneck + Fur Scarf + Black Leggings + Leopard Ankle Boots

Outfit #3
Parka + Tunic Sweater + Layering Top + Blanket Scarf + Leggings + Black Boots

Outfit #4
Wool Coat + Tunic Sweater + Layering Top + Fur Scarf + Necklace + Gray Jeans + Leopard Boots

Outfit #5
Parka + Gray Sweater + Layering Top + Blanket Scarf + Gray Jeans + Tights + Black Boots
chicago packing list winter
Outfit #6
Wool Coat + Gray Sweater + Layering Top + Fur Scarf + Leggings + Necklace + Leopard Boots

Winter 2017 Style Challenge – ON SALE

If you liked this Chicago packing list but missed out on signing up for the Winter 2017 GYPO Style Challenge, have no fear, we’re getting ready for round 2 of styling our 31 days of winter outfits and it’s now ON SALE for just $29!  Let me be your personal stylist for the remainder of winter. You’ll get a shopping list of winter trends and classics (including all the pieces in this post) plus a new outfit idea in your inbox every day for 31 days. Learn more and sign up HERE.

Getting my pretty on with Style ElixirA Little Bit of Everything, and Jolynne Shane.

I Feel Pretty Link Up

It’s the day of the week at GYPO where we celebrate what makes us feel pretty. Whether it’s a new outfit, hairstyle, or makeup, the I Feel Pretty link up is about anything and everything that makes your life prettier. Even if you’re not a blogger, you can still play along. Just tell me what made you feel pretty this week in the comments.

There are just a few simple rules:

1. Follow GYPO. (Bloglovin‘, FacebookInstagram or Pinterest)
2. Link up your pretty post.
3. Link back to GYPO.
4. Visit other pretties!

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Get your free Closet Staples Casual Capsule Wardrobe shopping list + four free outfit ideas!

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  1. haha! Yes, you have experienced what us midwesterners live through for months, and how it affects our fashion choices! A parka and face scarf is absolutely necessary!

  2. WHAT a great post! Love how you mixed and matched. I’m loving a large pendant necklace for travel idea.

  3. This is one of the most useful posts I’ve ever seen! My husband is going to think I fell and bumped my head when I pack in just one suitcase next time we go on a trip! I think I can do it using your suggestions! Thank you for a great post!

  4. Sorry! Its early.. i see you were in Chicago.. what was I thinking? Looks like you were well bundled and had a great time!
    jess xx

  5. Welcome to Chicago in January! That’s how we look this winter. Glad you had a great time. Your choices for things to do was spot on for tourists and natives alike. Hope you visit again soon!

  6. I love your choices and that bright blue is just the thing for a cold winter day! Another trick for your next visit…I have a Uniqlo ultra lightweight packable down jacket that I take and layer under a heavier coat. Kept me toasty warm during our January trip to NYC a couple of years ago! I also love mittens -they keep my hands warmer than gloves!

  7. Outfit #3 is a must have combination! I’m definitely going to try out this look! I’m always so jealous of the east coast during winter time because I wish I could wear more of these warm styles!

    ~ xo Sheree
    Posh Classy Mom

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