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An important thing to consider when you add anything new to your closet is versatility.  Does it compliment things that are already in your closet?  Will you be able to wear it for multiple purposes and events?  Does it transition well between multiple seasons?

Back in September, I shared this dress with you all.  In that post, I mentioned that one of the reasons I chose this specific dress was because not only did it scream fall to me, but it was also so versatile so I knew I would be able to transition it into winter when the weather started to cool down even more.

Asymetric Shift Dress & Ankle Boots for Fall
Dress: similar // Ankle Boots: exact, similar

Today, I’m sharing it again, but styled for cooler weather.  Fall is pretty mild here in NC – so before, you’ll remember I styled it really simply with a long necklace and ankle boots.

It’s still pretty mild here in NC, but the temperatures are definitely starting to fall.  So today, I’ve added some of my favorite cooler weather staples to make this dress work for this time of year, too.

Asymetric Shift Dress with Vest & Leggings for Fall & Winter
Dress: similar // Fleece Lined Leggings: similar, similar //Shoes: similar // Scarf: similar // Vest: similar

I actually wore this on our trip to Boston, and spent the whole day exploring the city in it.  It was the perfect, casual, no-fuss outfit.

To make this dress transition to the winter, I simply added some of my favorite pieces – a puffer vest, lined tights, classic Chuck Taylors, and a cozy infinity scarf.

2 Ways to Wear an Asymetric Shift Dress for Fall & Winter
Dress: similar // Fleece Lined Leggings: similar, similar //Shoes: similar // Scarf: similar

Another thing I LOVE about this dress, is that I am able to wear it so far into my pregnancy.  We are talking about versatility today, right?!

Loosely fitted dresses like this have been perfect to wear as my body continues to grow during this pregnancy.  Not to mention, great budget savers since they aren’t ONLY for this maternity season.

2 Ways to Wear an Asymetric Shift Dress for Fall & Winter
Dress: similar // Fleece Lined Leggings: similar, similar //Shoes: similar // Scarf: similar // Vest: similar

So, how can you transition your wardrobe from fall to winter more easily?  I actually think there are a few simple things to keep in mind that will make it easier.

Transitioning Your Closet from Fall to Winter

Look for versatile pieces that can be worn different ways. 

Shift dresses are a great example of something like this.  I picked long sleeves for this example, because I think they transition easier, but you can easily use a jacket if you’re working with short sleeves.  Some other great pieces include versatile sweaters and a great pair of jeans and leggings.

Pick Cooler Weather Gear Wisely

A simple denim jacket, cardigan, or puffer vest is perfect to help transition in the in between part of fall/winter when you need a little something extra, but aren’t ready for the full on winter jacket.

Lined tights

Ok, I can’t really emphasize how much I love lined tights and leggings.  I usually pick up a few pairs each season at TJ Maxx when I stop in.  They’re usually less than $10 and while they should NOT be worn as pants like leggings sometimes can be, they are perfect to wear under dresses when it gets cooler.

2 Ways to Wear an Asymetric Shift Dress for Fall & Winter

So, what do you think?  What are your favorite pieces to transition from fall to winter? Tell me below in the comments!

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For more of What Mama Wore, be sure to see here.

73 Comments

  1. You did a great job transitioning this dress into cooler weather! It’s so cute!
    ~Jessica
    Jeans and a Teacup

    1. Mary Leigh says:

      Thank you so much! I have enjoyed continuing to wear it in the cooler weather!

  2. Love these options, and congrats on your pregnancy!

    1. Mary Leigh says:

      Thank you so much! I have really enjoyed how versatile this dress has been both with the different seasons and pregnancy!

  3. How cute! The scarf and tights instantly transform it into another dress – looks so cozy! And perfect “bump” fashion (;

    1. Mary Leigh says:

      Thank you! It is the perfect non-maternity dress to still get through maternity season. We’re at 34 weeks now and I just wore it again yesterday!

    1. Mary Leigh says:

      Same. I actually wore this same dress again yesterday!

    1. Mary Leigh says:

      It really does make things so much easier to have versatile pieces in your closet!

  4. I really like this!! It must be especially comfortable during pregnancy, because it will always fit during and after! I need to get more shift dresses… 🙂

    1. Mary Leigh says:

      They really are great to have in your closet! They have been getting me through this pregnancy without having to buy a ton of maternity clothes. Now that we’re less than 6 weeks away from our due date, I am especially trying to not have to buy too many clothes that are only for this season!

  5. I love adding my tall boots to transition a dress to winter!

    1. Mary Leigh says:

      Oh, that is a great idea! I do love my riding boots, also!

    1. Mary Leigh says:

      Absolutely; you have a great link up! I have really enjoyed this dress this season, too!

    1. Mary Leigh says:

      Thank you so much! It was a fun dress to transition between the seasons!

    1. Mary Leigh says:

      Thank you; I have really enjoyed it!

    1. Mary Leigh says:

      Thank you so much! It is a really fun color to wear!

  6. I am all about buying pieces that I can transition between different seasons! I have a dress similar to yours (different color) and it’s so darn comfortable!

    1. Mary Leigh says:

      Right?! It’s nice to be able to have fewer pieces that are more versatile! And shift dresses are so comfortable to me, too!

  7. This is so perfect and flattering for any body type, wow! Love how it can also work for a gorgeous maternity look.

    1. Mary Leigh says:

      Thank you! I have been really thankful to find pieces that work for maternity also during this season!

  8. So many different looks combined into one! I love it. The dress looks super cute with the vest, and with your bump of course!

    1. Mary Leigh says:

      Thank you so much! I really do love how versatile it is!

  9. I really love anything I can wear and style in a few different ways, especially across seasons. A multitasking wardrobe is a must as a mom!

    1. Mary Leigh says:

      I totally agree! And I appreciate that it works with leggings, too – which totally makes it playground appropriate if need be!

    1. Mary Leigh says:

      Thank you so much!

  10. That color on you is great!! So versatile.

    1. Mary Leigh says:

      Thank you so much! It is really comfy and versatile!

    1. Mary Leigh says:

      Thank you!

  11. Fleece lined tights and leggings are THE BEST!

    1. Mary Leigh says:

      Right?! I love them so much in the winter! I just stopped wearing any other tights altogether because the fleece lined ones are just so much better!

  12. Don’t you love pieces that are versatile. It just makes it look like we have a bigger wardrobe.

    1. Mary Leigh says:

      Yes! It definitely helps to expand your wardrobe!

    1. Mary Leigh says:

      Same! I’m actually wearing a spring shift dress today with leggings and a sweater – it’s almost 70 degrees here!

  13. This is absolutely gorgeous!! And a pretty color

    1. Mary Leigh says:

      Thank you! I got this color for fall, but I have really ended up enjoying it a lot for winter, too! It’s such a deep, rich color!

  14. Love fleece lined leggings too! Ive been liking long cardigans with jeans or black pants.

    1. Mary Leigh says:

      I’m hoping to add some long cardigans (and tunic sweaters) to my wardrobe! And I definitely love a good pair of jeans!

  15. I love shift dresses. They provide such comfort and cute style that you can wear them on almost any occassion. You look great in yours!

    1. Mary Leigh says:

      I totally agree – they are really versatile!

  16. This styling would work perfectly in Texas winter too! This year it’s basically non-existent. 🙂 Love the vest and the sneakers — too cute.

    1. Mary Leigh says:

      Thank you so much! It really is great for mild winters! It was 70 today in NC! It will definitely be colder throughout the year, but overall, it tends to stay mostly mild here, too!

    1. Mary Leigh says:

      Thank you! I really do love the color. It’s a great, versatile dress to have in the closet!

  17. I love the shift style dress! And your transition ideas are so well put together- thanks girl!

    1. Mary Leigh says:

      Thank you so much! <3

    1. Mary Leigh says:

      Thanks so much! I definitely like to consider how many different ways I can wear something before it goes in my closet!

  18. Yes! I’ve been wondering how exactly I was going to do my fall to winter wardrobe… ty!

    1. Mary Leigh says:

      Leggings (specifically fleece lined), scarves, and fun jackets/vests – always my go to! <3

  19. Great tips for transitioning wardrobe! It’s great to find new ways to get through those times of the year!

    1. Mary Leigh says:

      Thank you very much! I definitely prefer things that are versatile!

  20. I love this dress and how you paired it with the accessories for both seasons! I just bought a shift dress and am going to be trying this style!

    1. Mary Leigh says:

      Shift dresses are so great for versatility. They can be worn across seasons and easily dressed up or down! I have a few in my closet that I really like!

    1. Mary Leigh says:

      Thank you so much! I have enjoyed this dress a lot and I appreciate it’s versatility across seasons!

  21. Love this post! I am all about versatility and I couldn’t agree with you more. A lot of the times I look at an item to buy I try to picture at how I can make it work for the different seasons. Investing in classic items like your shift dress and vest are really the best way to get the most bang out of our money and purchases. I love at how effortless you transitioned your outfit. It’s simple yet so chic. You look lovely! I hope you are having a great day.

    http://www.littlemisscasual.com

    1. Mary Leigh says:

      Thank you so much, Maureen! It really helps expand your wardrobe when things can be transitioned like this!

  22. Love these options!! Especially love when I can pair stuff with converse because comfort is king!

    1. Mary Leigh says:

      Oh yes – I have really been wearing my converse a lot this season!

  23. You look so lovely. Loved how you transitioned this look! I think jeans are my favorite to transition. So many kinds and you can wear them so many ways! Happy Holidays to you and your family!

    x Mary
    http://marymurnane.com

    1. Mary Leigh says:

      Thank you so much; same to you! I love a good pair of skinny jeans and ankle boots to transition also!

  24. These are great tips! I love using the same things from season to season- makes a smaller more manageable wardrobe stretch so much further! Loving that dress the color is perfect for fall and winter (I love burgundy for Christmas!!). You look adorable mama! Love to see your growing bump!

    1. Mary Leigh says:

      Thank you so much! I have loved your holiday style series recently, too! I loved the burgundy for fall, but now that it’s Christmas – I’m really liking it now, too!

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