> What I Wore - Fall Style Challenge Week 1 - Doused in Pink | Chicago Style Blog

What I Wore - Fall Style Challenge Week 1

If you are a regular reader, you’ll remember that I wrote about joining the Fall Style Me Pretty Challenge here.  It was a no-brainer signing up because I thought what better way to get my wardrobe ready for fall. When I received the shopping list I was happily surprised that I had every single piece already in my closet, and the list included some of the items I just purchased in September.  One of the things I struggled with before I started this blog was building outfits. I would buy things because I liked them or they were on sale, but never had any idea on how to style them, so they would sit unworn.  The style challenge gives you several ideas on how to wear the same piece different ways and who doesn’t want someone planning your outfits for you for 3 weeks? The fall style challenge is now underway and here’s what I’ve been wearing the first week.

ON Sweater / Sanibel Pendant / AG Stevie Jeans / Gap Scarf / Sam Edelman Penny Boot

What’s your favorite look this week?

 Thanks for reading today!

Linking up with these fabulous bloggers here and A Lovely Little Wardrobe.


  1. So many cute outfits, all perfect for everyday!! I especially love the first one, the rolled up jeans with your booties and great necklace go so well together.
    Marta, xo

  2. All these Fall looks are so cute and cozy, I love the first and last the most.


  3. Oh I am so glad you did the challenge and now I get to see your outfits! I love the first one. It's just so perfectly casual and yet still so stylish. I am lamenting my lack of a plaid scarf. You are just such a rock star!

    xo, Amy Ann
    The Real Arnolds

  4. Very cute looks! I would wear every one of them!
    Dawn Lucy

  5. My favorites are the printed shirt with the green utility jacket and the black Hunters w/ that beautiful plaid scarf... and that pendant necklace in the last outfit is beautiful! All of the outfits are something I'd wear!

  6. I love all of the looks, but the last one is my favorite! I just splurged on those same Sam Edelman boots and am in love, you styled them beautifully!


  7. Great looks. I'm like you and I just buy something because I like it without thinking about how it goes with other things. I love your first and last looks the best.

  8. Of course, every outfit is perfect, but I especially love the red plaid!

  9. That buffalo plaid looks great on you!! You are one of the lucky ones who looks nice in every color. I have been eyeballing those Toms wedges for a year. Should I put them on my Christmas list? Susan

    1. Susan, these wedges are so comfortable! I wear them all of the time and they feel like I'm wearing flats. You should put them on your list!

  10. Jill, I love your take on Alison's outfit. You rock the boots so well!

  11. These are all super cute! I think the one with the utility jacket is my fav though! Your boots are so cute!

  12. Love all the looks, the Autumn-ness of it all makes me so happy! I couldn't help also noticing the great Fall foliage view you have there, oh how I miss that~

    Pink Wings

  13. Yay! So glad you linked up with us. I love all these outfits, but I want to steal that plaid scarf that is now sold out.

  14. Oh I totally love the Penny boots!!! Nice color ON cardi!! Such fun looks Jill!!

  15. You rocked it!
    LOVING those Sam Edelman Penny boots- the slant at the boot top is so flattering!

    Le Stylo Rouge

  16. All of your outfits are SO CUTE. And you have the best collection of (sold out!!! Boo! lol) plaid scarves. You have such great casual, polished style. :)
    Gina - On the Daily Express

  17. Love all these looks! Second one is my favorite! There is something so fun about at that utility jacket!


  18. I am loving all of these fall outfits! They are perfect for this season!


  19. Sounds like a very cool challenge! I love the idea. My favorite outfit is #2 - the coat and relaxed style is my favorite.


  20. I love how you styled all of these! Fall fabulous :)

    xo, Shauna


  21. So many great outfits and cool casual layers. All of these outfits are still 100% you while still following the Fall Challenge. In love with all the 3 middle outfits, Jill.

    Have a Great Thursday Evening My Friend! <3 Ada.

  22. my computer keeps eating my comments :(
    try #3
    I want all your shoes.... ALL of them!
    Also, fall fashion was made for you, you look great in everything!

  23. WOW! Absolutely love the plaid scarf, sweater and hunter boot combination! My Fall uniform!!! LOVE LOVE LOVE all ur outfits! Great job! Hope you are having a wonderful day!
    Style Delights Blog

  24. Love all of these fall looks! I need your boot collection! ;)

    <3 Shannon

  25. Such gorgeous looks!!
    Martina xx


  26. Love your first and last outfit! So cute!

  27. I've never done the challenge before but it sounds like a lot of fun! And do I have to pick one?! I guess I would choose 4 but the decision is hard!!! Great looks, lady! Carylee | morepiecesofme.com

  28. I'm loving your fall style! Is it bad that as a "style blogger" my eyes and heart instantly gravitated towards the most comfy look of them all? Lol, I love that green ON jacket that you have!


  29. I love the grey and pink check scarf on you plus those brown boots are gorgeous. I've been looking for some just like these but can't find them anywhere. Love all the looks!

  30. Really like your outfits, Jill! Actually, my favorite is the first one - that is a super cute striped top and I like those jeans rolled with the boots. So glad you linked up!

  31. Oh I think I am loving the green jacket and scarf. I know that look has been around for several seasons/years but I still love it. Perhaps that makes it a classic. Thanks for coming to Fashion ITEM Friday and for placing the new and improved button in the line up you have. {and thanks for showing me more and more hops to see} ♥

  32. Love all your outfits. I do the same and buy all kind of things that look pretty and it ends up sitting because I have no idea how to style them.

    Thank you for joining TBT Fashion link up. Have a great weekend!


  33. I think the first look and the buffalo plaid are my favorites. But it was so hard to choose because you look great across the board!

  34. I love the way you styled everything, but especially the J. Crew sweatshirt!

    Tif @ Bright on a Budget

  35. So many great outfits. I love the idea of a style challenge but have personally never joined one (yet). It is great that you have a prompt every day, something that helps you look and think about your wardrobe in a new way. As usual thank you so much for taking the time to join the #reasonstodress real mom street style linkup, hope you can join again tomorrow!

  36. These are really cute outfits!! Warm and comfy!!!!


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