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Posh in Progress

2 Easy Ways For How to Style Sweater Dresses

By Stacey Freeman Leave a Comment

how to style sweater dresses 2
I’ve told you that sweater dresses are definitely my go-to right now. I love sweater dresses because they are so comfortable but look put-together without even trying. You don’t have to iron them and they are really low-maintenance. I wear sweater dresses for work and on the weekends. I thought it might be helpful to show you just how versatile sweater dresses are, so I decided to show you how to style sweater dresses in two ways. 

how to style sweater dresses
The first look, I wanted to show you that a sweater dress can actually be worn in a dressier way. I styled it with a mini teddy bear jacket and strappy sandals for a dress-up look. I would wear this for a happy hour or a casual date night. If you don’t have a teddy bear jacket, you could swap it for a leather or suede jacket. I personally like the cropped look because it feels more nighttime to me than a hip-length jacket. A long coat also can feel more dressed-up or maybe more work-appropriate, depending on the style of the coat. 

{Stacey’s Look 1: Dress; Jacket; Heels; Lip color}

how to style sweater dresses 3
{Stacey’s Look 2: Dress; Jacket (similar); Flats (similar); Earrings (similar); Lip Color}

For my second look, I went much more casual with a bomber jacket with faux fur lining and my favorite studded flats. I wanted to keep the look a lot more casual because I wanted to show you how to style sweater dresses in two very different ways. Personally, I prefer to wear a heel with sweater dresses because I think it makes my legs look better. The flats are a bit more frumpy. I often do wear white sneakers, like these, with sweater dresses too. Sneakers or flats definiteliy makes it easier to wear sweater dresses on the weekends. I can run errands or play with my kids when I’m wearing ultra comfortable shoes. 


This is just two ideas for how to style sweater dresses. As another option, you could wear tall brown flat boots with a long cardigan for a slightly elevated casual look. Another idea would be to wear tall suede heeled boots with a matching suede jacket for a sexier feel. Plus, there are so many different ways to style sweater dresses, the options are really unlimited. 


Are you looking for other sweater dress inspiration? Click here. 

Tagged With: how to style, Shein, style tips, sweater dress, sweater dresses

About Stacey Freeman

I am a Style Maven, Mommy, Educator, and Traveler.

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Stacey Freeman, Ph.D.
When’s the last time you accomplished something When’s the last time you accomplished something you never thought you would? 

I still can hardly believe I’m a published children’s book author. This isn’t my first time being published; I’ve written many academic papers and even a book chapter with a colleague about museum activism. But a children’s book? I never imagined or dreamed I could.

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My kids will be attending @galileocamps this summer, and they are so excited! Camp Galileo is an award-winning summer day camp that uses project-based learning and STEM principles to help develop innovators. They have over 65 summer camp locations across Northern and Southern California, Chicagoland, Denver, and Seattle. They offer innovative camp experiences for kids as young as pre-K up to 10th grade. Plus, they also offer flexible scheduling to help working families. If you're interested in learning more, visit poshinprogress.com to read about my kids' experience last summer and why they are so excited to go back this year. Also, you can save 15% with code POSH15 when you register at galileo-camps.com #ad @galileocamps #summercamp #lamoms #lamom #lasummercamp
Jacaranda season in my new babydoll dress 💜💜 Jacaranda season in my new babydoll dress 💜💜

Not pictured, me trying to walk casually on the sea of jacaranda flowers as my heels continually sink into the grass 🤦🏼‍♀️🤣💜.

New on poshinprogress.com, I’m sharing the cutest long sleeve baby doll dresses for spring. Link in profile or stories! You can shop my favorites here: https://liketk.it/3Frgk

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CA friends, have you been to the @the_flower_field CA friends, have you been to the @the_flower_fields yet? This week is your last chance to see all the stunning ranunculus flowers. If you’re looking for other fun thing to do in Carlsbad, head over to poshinprogress.com or link in stories! 

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Happy Mother’s Day to all the moms in all of the Happy Mother’s Day to all the moms in all of the forms ❤️. I appreciate you and all of the selfless and unseen things you do. 

R & G, you’ve changed my world so completely. You’ve taught me unconditional love, patience, and cherishing the moment. I am the luckiest. 

And a very Happy Mother’s Day to my mom and gram @debvicario2 - we miss your weekly visits, come back! 

Lastly, motherhood is a choice which requires great effort and sacrifice. A woman’s reproductive health is for her to decide.

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