Downtown Chicago


The hustle and bustle of the City never gets old…My family and I spent the weekend downtown, followed to a trip to Ravinia to watch the Symphony play classic children music. Continue reading to learn more.





Downtown Chicago will always have special place in my heart. I’ve been calling this City home for the least 10 years but I do think eventually it’ll be time to move. Summer’s are beautiful in the City (there’s no other city I’d rather be!) but Winter’s are cruel. I have such a hard time with them year after year…But let’s change the subject, shall we?

New York Fashion Week is currently going on and I’m bummed that I didn’t quite make it this year. Once I will share my surprise announcement you’ll find out why, and everything will make sense!  I typically don’t like to have secrets but this one just needs to wait a little longer until…Do you have any guesses?

On a different note, I’m grateful that I was able to spend the entire weekend with my family and friends. We took my son to Ravinia to see the Symphony play music to some of his favorite books/movies, such as Winnie The Pooh, etc. It was so fun!

As always, thanks much for reading & have a wonderful Monday!

Much love.





  1. September 12, 2016 / 1:09 AM

    You look so beautiful, Vanessa! I just love your pleated maxi! Eager to hear your announcement! You’re pregnant…. you’re moving… you’re partnering with another fabulous brand?! Okay… I’m all out of guesses, I guess I’ll just have to wait this one out! ๐Ÿ™‚

    xo, Jennifer

  2. September 12, 2016 / 1:20 AM

    Oh my goodness how wonderful! I just loved Winnie the Pooh growing up he was my favourite ( maybe still is ๐Ÿ˜‰ ) I very excited to hear your announcement! The winters out east are very rough. All of my family is in Toronto and we don’t visit in the winter for a reason! I will stick with summer visits!

    Wishing you the best Monday !

    Lots of love … Sydney

  3. September 12, 2016 / 1:22 AM

    I have a guess but I am not saying! Aren t those pleated skirts just great! I am so happy to see they are a hit this fall too!

  4. Andrea @ Living On Cloud Nine
    September 12, 2016 / 5:39 AM

    Oh how that lovely skirt just simmers!!! We done downtown Chicago, I bet you had the best time!! You look as beautiful as ever!! Have a great Monday sweetness!!

  5. September 12, 2016 / 6:55 AM

    Yay for weekends in the city that sounds like so much fun! And I hope he enjoyed the symphony that is serious so fun! You look so gorgeous obsessing over those shoes so fun! As always looking so fab!

  6. Cora
    September 12, 2016 / 7:08 AM

    Perfect outfit, love the channel handbag..Have a good start in a week..

  7. September 12, 2016 / 7:16 AM

    Chicago winters are very similar to our here in the prairies, they can be so cold and the windchills just make it worse. I feel your pain. I’m loving your pleated skirt, it’s such a classic and elegant look. I’ll wait for you to announce your surprise but I’m pretty sure I already know what it is. And I’m so happy for you and your family! It’s a beautiful thing๐Ÿ˜Š Hope you have a great week beautiful!

    xo, Jackie

  8. September 12, 2016 / 7:54 AM

    I’ve always wanted to visit Chicago! I wish I could have met you at NYFW while I was there but I can’t wait to hear your big news! Have a great week.

    xO – Steph

  9. Bubbe
    September 12, 2016 / 8:14 AM

    Love it all: the pleated silver skirt, the delicate cami, the unstructured blazer, the Chanel bag, Super sophisticated look for late summer in the City.

  10. September 12, 2016 / 9:07 AM

    You are so downtown chic, Vanessa! What a perfect look for the city. Love the black and white combination with the gorgeous Chanel. Have a great start to the week!

    xo, Rachel
    A Blonde’s Moment

  11. September 12, 2016 / 9:09 AM

    I absolutely love this look!! I have been looking at pleated skirts a lot this week because I think they add such a fun element to the outfit! You look gorgeous and I hope you have a wonderful week! Can’t wait to hear the surprise (I have my guess!)

    xo Bryn

  12. September 12, 2016 / 9:21 AM

    what a gorgeous look Vanessa, I love the pleated skirt super cute! wishing you a wonderful day.

  13. September 12, 2016 / 9:34 AM

    VANESSA! I’m in love with your gun metal liquid silver skirt (do those words even make sense together?!) Love this chic look! And as for ze announcement, hmmmm you’ve been chosen as brand ambassador for a brand, bagged a campaign, omg you got a TV show…I’m getting quite excited, haha! Xx

  14. September 12, 2016 / 9:48 AM

    Such a fab look! I am loving metallic pleated skirts at the moment, I really need to get one! Can’t wait to hear what your surprise is!
    x Emily

  15. September 12, 2016 / 10:07 AM

    You always look so gorgeous Vanessa, I can understand why you love Chicago so much and I bet the winters are so harsh it would make you leave. I am sorry your couldn’t go to fashion week but my guess is that you will go to London? Paris? Milan? I hope you do!

  16. Tamara
    September 12, 2016 / 12:10 PM

    Looking sooo chic Vanessa! I adore your outfit today!


    Tamara –

  17. September 12, 2016 / 12:39 PM

    You look absolutely gorgeous, Vanessa! I adore this entire pairing, which is so chic and full of texture and detail, it has a very city girl feel, perfect for the topic of your post today! I’ve never been to Chicago before, but I’ve heard it’s quite amazing and I, of course, hear so much about the deep dish pizza and I’m pretty much obsessed with pizza. It sounds like you had a great weekend and I’m sure your son loved the symphony, it’s one of those things that both parents and children can enjoy equally. I can’t wait for you to share your exciting news with us, I honestly have no idea what it could be! I hope you’re having a very Happy Monday and thanks so much for the inspiration as always, beautiful!



  18. Amy Arnold
    September 12, 2016 / 1:17 PM

    I loved Chicago when we visited and want to come back when I can explore more and meet YOU! You look so chic and perfect for spending some time downtown. Love the skirt. You know I am a sucker for anything midi length. The anticipation is building for your announcement!

    Amy Ann
    Straight A Style

  19. September 12, 2016 / 2:42 PM

    This looks like a great outfit for pretty much anything. I just love the white blazer, V. Happy Monday. xx

  20. Izabela
    September 12, 2016 / 3:01 PM

    You look stunning Vanessa. I adore pleated skirts and I’m so happy they are still going strong.

  21. September 12, 2016 / 5:18 PM

    Well, I think I know about the announcement, dear V.! I wrote about it last week ๐Ÿ™‚ Well, then there are new Fashion Weeks, I am sure you will make it, really! I loved the outfit you are wearing, nice blazer, lovely skirt and always so chic and sophisticated, my dear friend! Gorgeous! I loved the fact that you went to the Symphony for children! It is so important to start early! I hope you have a very beautiful weekend, just like you are! Can’t wait for the annoucement! Hugs and kisses!

  22. September 12, 2016 / 5:48 PM

    What a great look! I love the pleated skirt and white blazer. You look like a million bucks! Where would you end up moving too? Chicago is so beautiful, but I totally understand what you’re saying about the winters. I’m from Pittsburgh and the winters there seemed to last from November to May!

    Love, Lindsey

  23. September 12, 2016 / 7:23 PM

    You have me on the edge of my seat waiting for your surprise! I am so excited to hear what it is.
    PS. I love this outfit! You look gorgeous as always. Happy Monday, V!
    Julia // Little Miss Haute Couture

  24. September 12, 2016 / 10:26 PM

    Girl you are sooooo having a baby right? ๐Ÿ™‚
    Love love this look! I love being a tourist in Chicago too, and yes, it’s the best city during Summer. I don’t like Winter but I’m not thinking of moving out just yet ๐Ÿ˜‰
    Have a great week ahead gorgeous!

  25. September 12, 2016 / 11:28 PM

    Chicago makes for such a gorgeous backdrop, doesn’t it? I haven’t spent much time there but LOVE that city. I love that skirt of yours almost as much, it is so fabulous! I love that it can transition so well into autumn and winter, you’ll be able to wear it for months to come!

  26. September 13, 2016 / 1:29 AM

    I love this metallic pleated skirt! I saw a very similar one at Zara a couple weeks ago, and I almost bought it!
    Ooh I have guesses about your secret. Sounds like you might get even busier soon ๐Ÿ˜‰


  27. September 13, 2016 / 6:15 AM

    Are you pregnant? I think that’s the announcement, am I right?? I hope when you move out of Downtown Chicago to your new place you will bear the winter better. I love this look, the metallic skirt is so edgy, you look amaze balls and your tattoo are goals!!

  28. September 13, 2016 / 6:40 AM

    You look classy. Loved this post. Such a lovely outfit.

  29. marta
    September 13, 2016 / 7:57 AM

    Hi Vanessa, so glad you had such a great time with your family in downtown Chicago!! I would love to visit some day but I do hear you on the harsh winters, Toronto winters are just brutal and I would love to move somewhere warm all year round if I could!! You are looking so beautiful, classy and glam in this outfit! The white blazer and Chanel purse are perfection! Hope you are having a wonderful week & I’m really excited to hear about your news. Have some ideas but not sure what it’ll be. xoxo

  30. September 13, 2016 / 2:38 PM

    You look beautiful Vanessa. Love that skirt!
    What a chic look to walk around Chicago. It’s the best city during Summer I agree!

  31. September 13, 2016 / 2:46 PM

    Love this look, can’t wait to hear the announcment

  32. September 13, 2016 / 6:14 PM

    Beautiful outfit! That skirt is so striking with the metallic-ness of it. And you can never go wrong with a monochromatic look. ๐Ÿ˜‰

    Hope you are having a great week!


  33. September 13, 2016 / 8:48 PM

    I love chicago, I grew up super close to there and spending the weekends on michigan ave was my fav.
    your skirt choice is perfect also.


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