How to Pair a Dress with Boots this Fall


If you’re like the me two years ago, you probably walk into stores confused when they have racks and racks of dresses on display. It’s cold outside, so why would anyone want to be wearing a dress unless it is for a special occasion.

For years, I had that same thought, and even when leggings became the new pants, I was still hesitant to purchase a dress during the cold weather months. But then I began realizing that wearing a dress during the colder months is all about what you pair your dress with.

If you’re attracted to the many styles of dresses that are hitting the racks in your favorite stores this season, but you are not making the purchase because you’re afraid of the cold – my advice is to rely on your boots.

The best way to wear a dress this season is to pair it with either a pair of over the knee (OTK) boots or boots that just reach right under your knee. Therefore, you’re legs are too exposed.

Most boots sold during the fall and winter seasons are made of materials that are meant to keep you warm, and even if they are not, they are made with enough room for you to slip those must have leg warmers on to fill out the boots and to keep your legs warm in the meantime.

And if that isn’t enough for you, there are so many shades of leggings so you’re guaranteed to rock that dress to the fullest extent no matter how you choose to wear it. Don’t be afraid to take that dress that is calling your name right off the rack and head to the cash register with a confidence that the dress will keep you warm.

Recently, I found this lovely plaid print, off the shoulder dress at the new Anthropologie at the King of Prussia Mall. Have you visited the store yet? If you haven’t, you must.

This dress just spoke to me when I was in the store and honestly, it is warmer than it looks. To cover up those bare legs, I paired my dress with adjustable OTK boots and a warm wool scarf to keep my legs, shoulders, and neck warm.

fall outfit fall outfit anthropologie off the shoulder dress fall outfit anthropologie off the shoulder dress


Plaid OTS Dress – Anthropologie

Tan OTK Boots – Charlotte Russe

Wool Wrap Scarf – H&M (similar here)


  1. MarvelousintheMidwst
    November 14, 2016 / 1:42 pm

    love that dress! It looks so comfy and is paired perfect with those boots!!

  2. Hannah Shanae
    November 14, 2016 / 11:14 pm

    Those boots are adorable and I love that dress on you!

    Hannah Shanae

  3. November 15, 2016 / 9:08 am

    love this classic piece! it’s going to be 80 degrees in Texas today, so bring on the dresses!
    Southern Elle Style

  4. Dasha Guyton
    November 15, 2016 / 10:02 am

    These days I’m all about dresses, so thanks for the tip!


  5. November 15, 2016 / 1:38 pm

    Love me some Anthro! The dress is super cute! xo

  6. November 17, 2016 / 3:45 pm

    You have me loving fall with that look. It’s time to go shopping for a new dress and pair of boots. Maybe leg warmers, too.