My Hunt For Winter Dresses

My Hunt For Winter Dresses
My Hunt For Winter Dresses
My Hunt For Winter Dresses
My Hunt For Winter Dresses
My Hunt For Winter Dresses

The one thing I gravitate towards the most in my closet in the fall and winter are my jeans. I live in them. Recently I’ve had some fun events and dinners and all I can seem to put together in my closet are more outfits with jeans. It’s definitely on brand for me, but it’s also not super comfortable when you’re sitting in a 10 inch rise pair of jeans and stuffing your face full of delicious food. It was time to figure out some DRESSES!

This is never a problem for me come summer. But it’s apparent that I no longer own great winter dresses that can be layered with leggings and boots to stay warm. I must’ve gotten rid of so many during my KonMari cleanout. And I feel like it’s because I haven’t figured out my dress vibe. Who am I when it comes to fall and winter dresses?I think the reason why most of my fall and winter dresses are gone is because they weren’t “me”. So now the challenge is to figure that out.

I scoured Pinterest and some of my favorite stores looking for inspiration. And to be honest, the winter dress selection is abysmal. Sure I went towards the end of the season. But I shop a lot (thanks to having a fashion blog) and I know what’s out there. The styles just aren’t really something I get super excited about. I mean it’s the whole reason why I wrote this blog post, was to get excited about winter dresses! Sure I know HOW to wear them, but it’s finding the dress that I need!

The Winter Dress Style I Hate

The one thing I think I’ve been able to do is narrow down things I hate when it comes to a winter dress. And this is solely that I hate it on ME. How I wish I could wear some of these styles, but they just aren’t for every body type. And that’s a chunky sweater dress. Especially a dolman sleeve. NO THANK YOU. With broad-ish shoulders and a larger chest, this makes me look 100 lbs heavier. Or at least makes me FEEL that way.

I’m also not into anything that’s shapeless. When you have a curvy figure, meaning hips, butt and boobs, doesn’t matter your size, shapelessness can be super unflattering. These styles look great on taller folks with a leaner build (as in no boobs).

shop sweater dresses I wish I could wear

The Winter Dress Styles I’m Searching For

Since I’m hoping to keep my legs looking as long as possible and my upper half looking not bigger than it is, I think this may mean a few things for me. It may be time for mini dresses that can easily be paired with fleece-lined tights and boots to stay warm. And even topping with my favorite long blazer would create a stylish and flattering shape. Then there are midi dresses that are figure-flattering with a v-neck like in today’s look. Sure my legs are still cold, but I guess I could always add some tights.

Once I ditched my day job, I feel like the idea of tights with skirts or dresses just went out the window. But it’s a combination I personally love and feels so nostalgiac since I had to wear that for private school in Montreal as a kid. It’s definitely time to bring that combo back!

shop non-sweater winter dresses I’m eyeing

Photos by Hannah Lozano

Jessica is an Atlanta life and style blogger. Aiming to bring practical tips to your every day life. Tips that you can easily tackle and make your life feel just a tad more 'put-together'.

Leave a Comment


  1. 2.24.20

    One day, one day! You will find your winter dress style! LOL

    Cathy, your Poor Little It Girl

    • 2.24.20
      Jessica said:

      One day! I think I just have to remember boots and tights work too!

  2. 2.24.20
    Laura Leigh said:

    & Other Stories has amazing dresses for winter season! And I’m with on the lack of ability to rock an amazing chunky sweater dress. Just cannot do it. Looks terrible. Hate that you’re experiencing the same thing but have to be honest, glad I’m not alone ha.

    xo Laura Leigh

    • 2.24.20
      Jessica said:

      I envy people who can wear them. I just can’t do it! Your maxi with the booties is what sparked this all. Like WHY CANT I WEAR THAT and not jeans?! I do love & Other Stories, but with it being the end of the season, I may need to mark my calendar for September to “shop all the best dresses” ha!

  3. 2.24.20
    Jennifer said:

    Your dress is so cute! Thanks for sharing. 🙂

  4. 2.25.20
    Lisa Autumn said:

    I love the dress you are wearing!

    Lisa |