The Happy
Side Hustle Planning Kit

    I respect your privacy. Unsubscribe at anytime.

    5 Tips For Rocking Dresses This Winter

    December 22, 2017 Amanda Cross 5 min read
    Note: This post may contain affiliate links. Please see my disclosure for more details. Thanks for supporting the brands that make The Happy Arkansan possible!

    I love wearing dresses! Before you click away from my blog on that fact alone, hear me out. Wearing dresses is basically the ultimate in lazy-girl fashion. It's one piece of clothing that you can slip over your head and it instantly makes you look more put together (even if you aren't!) Plus, it's way more comfortable to maneuver in over its romper one-then-done counterpart. Have you ever tried to potty in a romper? It's pretty difficult. So, even though I love a good romper, I will take a dress any day. So, today, me and my wrinkly dress (don't @ me), are going to show you how to rock a dress even when it's cold outside.

    Five Tips For Rocking Dresses This Winter | The temperatures might be dropping, but you can still rock a dress if you want to. Click through for today's blog featuring my tips on how to rock a dress even when it's cold outside. #WinterStyle #ColdWeatherStyle #FashionBlogger #Fashionista

    1. Pick The Right Dress

    The first thing you need to do to rock a dress in the winter time is pick the right dress.

    Yes, Janet, you will be cold outside if you pick a tank top or sleeveless dress. Get a better dress, Janet!

    Don't be like Janet, y'all (sorry if your name is Janet.) Instead, pick a nice warm(ish) dress to be your base dress. Have you ever heard of a sweater dress? They are pretty cool (warm). I mean, they are dresses made of sweater material, how much warmer can you get?

    Also, think about the length of your dress and the length of its sleeves. Obviously, you will be cold if your dress barely covers your butt or you are wearing a short sleeve dress. You may want to go for a maxi/midi dress or one with long sleeves. I am always down for a dress with bell sleeves too.

    This dress from JustFab doesn't have the thickest material, but it's definitely not the thinnest. It also has long sleeves and it covers a good portion of my body which is great for a winter dress.

    2. Add All The Layers

    I didn't have to layer too much with this look, but there are so many ways to layer your dresses. This is especially great when you want to bring a more spring-y dress for the winter months.

    Here are a couple of suggestions:

    • Cardigans: This is the tried and true method of layering dresses. It can get a little bulky and hide the true potential of your cute dresses, though.
    • Arm Tights: I learned about this because one of my Lilly loving friends was wearing this under a few of her Lilly Pulitzer dresses to pull them into fall/winter. Spanx recently introduced these magical inventions and they are great because they go under the dress not on top of it like a cardigan would. These things come in all sorts of colors and textures so you can find some Arm Tights that works best for your wardrobe.
    • Leggings/Tights: Leggings can truly help you out in your time of need so you can cover up your legs a bit so they don't freeze while you wear your cute dresses.

    Layering is key, y'all! If you want to avoid getting all cold outside, you are going to have to put a few layers on your body!

    3. Boots Are Your Best Friend

    Next, you need to wear some cute boots. Boots will save your booty in the cold weather. You want to invest in some cute knee-high or even thigh-high boots. The longer your boots, the less of your body is exposed to the wind and elements of winter.

    I personally wore these boots I got a few seasons ago from JustFab. They, unfortunately, aren't available on the JustFab website anymore, but many places have similar tan knee-high boots.

    You can also pair your dresses with a cute pair of booties if you add some leggings as a layer to keep your thighs and legs warm.

    4. Find Some Cozy Accessories

    Next thing, add some cozy and cute accessories. Scarves are all the rage this time of year and can definitely help you keep warm around your neck. You can also add some gloves, stockings, or a felt floppy hat to keep your head warm in the cold months ahead.

    Whatever accessories you decide to add to your dresses this winter, make sure they help you feel comfortable and cozy so that you can wear your dress happily.

    5. Find Your Inner Diva, Girl

    Wearing a dress in the winter is going to be cold, y'all. You need your inner diva to come out so you feel fierce af and you don't care about the cold anymore. My sister always says, “beauty is pain,” and I say “wearing dresses in the winter is cold.” When you get over that fact, you can actually enjoy wearing dresses more.

    Most likely you will be inside anyway, so it won't really matter how cold it is outside. The fact that I am going to be inside soon is literally what got me through all of my winter dress wearing in college and graduate school. So, swallow the ickiness of being outside for a few minutes while you get to class or work, and then reap the benefits of a whole day of looking fine AF.

    Pose in the mirror, have a dance party in the morning, do whatever you have to do to get psyched up to wear your beautiful outfit. Dresses were not meant to be abandoned for 1/4th of the year!


    I don't like to let the seasons dictate what I wear. I will wear spring-like colors in the winter time and not bat an eyelash. You don't have to let the seasons tell you not to wear the things you like to wear. You don't have to let the winter or fall tell you that you have to be drab instead of fab. Be smart and don't get sick but wear the things that make you feel happy in the end.

    Shop Today's Outfit

    This outfit features the Flutter Sleeve Dress from JustFab. It is sold in size XS through 3X and it comes in three different colors. I got a 2X in this dress.

    Follow Me:

    1 Comment

  • Lauren December 23, 2017 at 12:23 am

    You look amazing, Amanda! I love dresses & boots in the winter!

    Lauren //

  • Leave a Reply

    About Amanda

    Hey Y’all!
    My name is Amanda Cross, and I am the blogger behind The Happy Arkansan. I am a blogger, freelance writer, and podcaster. When I am not creating content for any of my content online, I can usually be found baking, watching YouTube, or napping. I love helping millennials and young adults navigate the mess that is adult life. Keep reading for my thoughts and experiences.

    Subscribe to Blog via Email

    Enter your email address to subscribe to this blog and receive notifications of new posts by email.

    Join 450 other subscribers