How to: Dress up your flannel

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photos by Jessica Kaylene Photography

Being a Midwest gal, flannel is a staple in my closet. On any given day between November-April in Michigan you are guaranteed to see at least 40-50% of the population in flannel.

Winter parties in college? Flannel on girls and guys.

Casual night out at the bars? Flannel.

Holiday parties? Flannel.

Sunday morning brunch? Flannel.

Wednesday night grocery shopping?  Flannel.

What can I say, we like our flannel in the Midwest.

The best thing about flannel (other than the obvious coziness), is how versatile it can be. You can pair it with jeans, with a leather jacket, with a vest, with sequins, with your sweatpants, or in this case, faux leather.

This flannel is actually a dress I shared on Instagram Friday (HERE) but it worked well tucked into this J.Crew faux leather skirt (currently on sale!). Best thing about this skirt? It’s long enough to wear to work (at least in my book), making it WAY more versatile than my faux leather miniskirt from Express (HERE).

I opted to dress it up this with the tassel earrings, heeled boots & skirt, but the dress works just as well with sneakers & a quilted vest.

Tell me, are you a flannel fan?

xo, Maddy

Shop my look:


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  • Reply Kristina

    I have this skirt too and love it!!! I’ve definitely worn it to work too…

    November 21, 2016 at 5:37 pm
  • Reply Emily

    I’m pretty obsessed with this entire look 🙂 That bag…I’m in love!!


    November 21, 2016 at 6:30 pm
  • Reply Nermisa

    I love EVERYTHING about this look.
    Outfit = on point
    make up = on point
    post = on point.


    November 21, 2016 at 7:10 pm
    • Reply madelinewp

      you’re too darn sweet. thank you so much Nermisa!

      November 22, 2016 at 5:18 pm
  • Reply Nikki

    I love me some flannel!! Dressed down, dressed up, whatever. I am cold all of the time so flannel and I get along well. This is such afab look! I love it!


    November 21, 2016 at 8:54 pm
    • Reply madelinewp

      thanks so much Nikki – and yes, flannel is the BEST!

      November 22, 2016 at 5:18 pm
  • Reply Monochromatic Holiday Style (+colorful feelings) - cassidy lou

    […] shades of green lately. It started with this H&M skirt (worn here & here), continued with this flannel shirt dress, and is now full blown with these Banana Republic heels, ASOS dress and the teal LOFT skirt I wore […]

    December 14, 2016 at 6:54 pm
  • Reply Sweat Pants Blog

    Dress Up Any Outfit With The Lou

    […] oset. On any given day between November-April in Michigan you are guaranteed to […]

    May 26, 2017 at 8:07 pm
  • Reply Falling for Flannel - cassidy lou

    […] I’ve talked about before, but flannel is the fall/winter uniform of the Midwest, no matter your gender. Actually, I wrote about it last fall while wearing this exact same flannel…except it was tucked into a leather skirt.  […]

    October 22, 2017 at 1:56 pm
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