How to transition from fall to winter: simple hacks with J.Crew

timeless-optimist-fashion-blog-how-to-transition-from-fall-to-winter-simple-hacks-with-j-crew .jpgtimeless-optimist-fashion-blog-petite-fashion-j-crew-fair-isle-turtleneck-sweatertimeless-optimist-fashion-blog-how-to-transition-from-fall-to-wintertimeless-optimist-fashion-blog-petite-fashion-j-crew-sweater-j-crew-jackettimeless-optimist-fashion-blog-petite-fashion-j-crew-italian-double-cloth-wool-lady-day-coat-with thinsulate®

The first snow fall has officially arrived to some of us in NY Tri-state area. Winter can be so magical but very miserable for people like me who never can seem to stay warm. Thankfully, I found a new great pieces from J.Crew last week during an online shopping spree that are great for layering and will be keep you toasty warm.

To start my look, I went with this darling turtleneck sweater. I am wearing it in a size XS with the intention of not leaving it in the dryer long. I am not sure if it is going to shrink or not but I am not taking any chances! If you have struck sweaters in the past, I would recommend sizing up.

The next step is to layer up with a jacket! This J.Crew wool lady jacket is one that I have admired for years. It is lined with Thinsulate which give the coat extra warmth. Think of it like wearing a parka with a lot less of the bulk. In these images I am wearing in in a petite 0. I will be honest, the 0 was a bit too small around my shoulders. So I did even up exchanging it for a petite 2.

Finally, finish up this look up with a neutral bag, a pair of your favorite booties and your favorite pair of jeans then you are ready to go! As temperatures get lower, you can easily slip on some gloves and a cute wool knit hat. What are some ways you transition from fall to winter? Chat with me by leaving a comment below!


Jacket: J.Crew // Sweater: J.Crew // Jeans: BLANK NYC; similar here // Boots: Nordstrom // Bag: OLD; similar here; vegan leather option here

About the blog

Timeless Optimist is a petite fashion, beauty & lifestyle blog by Cristina Medina. This page focuses on creative storytelling, photography and positivity.

Follow Along

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. 11.21.17
    Kylie said:

    J Crew is such a perfect classic! LOVE this timeless look!

    • 11.21.17
      Cristina said:

      Thank you Kylie! I agree, J.Crew is the best.

  2. 11.21.17

    Jcrew is just perfect for all seasons! Really loving the sweater and jacket combo! Perfect fall to winter look!

    Sarah Lindner

    • 11.21.17
      Cristina said:

      Thank you Sarah! I’m so glad you like it. The sweater is a piece that I think will look amazing on everyone.

  3. 11.21.17

    Making the transition from Fall to Winter attire can be so difficult, but I love what you’ve come up with!

  4. 11.22.17
    Kim said:

    That jacket is such a classic and timeless piece. You will get so much wear out of it!


  5. 11.22.17
    Maggie said:

    You can never go wrong with j crew! I love this sweater!

  6. 11.22.17

    I loved reading this post so much! You look adorable and this sweater is gorgeous.

  7. 11.22.17

    What a great sweater! J. Crew always has the best pieces.

  8. 11.22.17

    What a cute look! I need this sweater!!

  9. 11.22.17
    Shelby said:

    You are gorgeous girl! I love this classic coat!


  10. 11.23.17
    Mckenna said:

    I live in Ithaca and can’t believe we have had already had snow lol!! Being from the south it’s crazy to me!!

  11. 11.23.17
    Danielle said:

    Such a great fall look! That jacket is such a classic and is just gorgeous!

    xx, Danielle | Pineapple & Prosecco

  12. 11.23.17

    Loving this turtleneck and coat — you look gorgeous!

  13. 11.23.17

    That coat is so gorgeous! So thankful for these tips!

    xx, Tomi

  14. 11.23.17

    This is a great sweater! Love the colors and style.

  15. 11.23.17

    Love J.Crew!! They always have such great staples for Fall and Winter!

    xo, Laura

  16. 11.24.17
    ashleyharg said:

    I literally want everything you are wearing! That coat is so chic and such a great color!

  17. 11.24.17
    sewsarahr said:

    This sweater is so pretty on you! The colors are just gorgeous with your hair and skin tone!

  18. 11.26.17
    Mindy said:

    Love the layers! Super cute

  19. 11.27.17

    I’m all about the strategic layers, especially during this time of year.

    Birdie Shoots

  20. 11.27.17
    Hillary @ Style in a Small Town said:

    Love this look! That sweater is beautiful!