Plaid Flannel Shirt Styling

Midlife women wearing flannel shirt, James Perse dress and Stuart Weitzman OTK boots

When I think of plaid flannel, the first thing that comes to mind is Grunge. Grunge hit the scene in the early nineties, right at the tail end of my drinking and using. By late 1993, I was sober, and by April  1994, Grunge was dead along with its King, Kurt Cobain. To say I missed the whole scene isn’t exactly true. I was living my own grunge scene just centered around House Music and Raves. I am pretty sure I didn’t own a single flannel shirt.

Favorite Flannel 

Grunge has resurfaced again as all fashion does. This time around, it encompasses the traditional grunge look of flannels and ripped jeans but with decidedly more feminine appeal, including dresses, pastels, and soft details combined with the harder edge pieces. As a result, flannel is having a major moment, and this time I am all in.

My favorite button-up shirt brand is Grayson. You can read my full review of Grayson Button Up Shirts if you are interested.  So when I decided I needed a plaid flannel, it was a no-brainer to look there first. I am also a fan of Madewell flannel shirts. I prefer a soft, lightweight flannel that I can layer. California winters are mild in comparison, and rarely do we need a heavy-duty flannel.

Another great place to pick up inexpensive flannel shirts is traditional teen retailers like Abercrombie & Fitch, Hollister, American Eagle, and Tilly. Even Target has a great Women’s Plaid Oversized Flannel for $20. I opted for a quality flannel as I know I will use it over the years but if you just want to get in on the trend, try one of the less expensive options.

Shackets are another big trend for fall. A shacket mimics a plaid shirt but with a quilted or sherpa lining for warmth. The whole shacket trend isn’t that practical in CA. A few days a year, I need a truly heavy jacket when most often, a sweater will do. I am on the hunt for a lighter weight shacket to recommend.

But you can easily substitute your favorite flannel as a shacket.  It is all about styling. There are so many great ways to wear plaid flannel for winter.  Here is how I am wearing plaid flannel this year.

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How to Wear Plaid Flannel 

Outfit #1: Flannel + Black Jeans + Lug Sole Boots

I am wearing the Grayson The Hero Buttondown in Red plaid. It reminds me of a subtle Christmas plaid but works throughout the cold-weather season. Add a pair of black jeans and lug sole boots for a quick and easy outfit. The white boot gives this outfit a modern vibe. My boots are the Lucky Brand Ellerey Boots and under $100! These boots are waterproof and look so similar to the Stuart Weitzman and rag & bone boots but at a fraction of the price.

Over 50 women wearing flannel shirt, black jeans, Utility Jacket and white lug sole boots.

Outfit #2: Tie Up Your Flannel

This look should really be 1A, but without a 1B I just couldn’t do it. I thank my 8th grade English teacher for that one. If you want a more polished look to your simple flannel shirt outfit, just tie up the front. The look is more tailored and figure-flattering. I’m wearing my same Lucky Brand boots because I may not take them off all winter, but you could easily wear them with your favorite sneakers or flats.

Over 50 women wearing plaid flannel, black jeans and white lug sole boots.

Outfit #3: Flannel + Cropped Sweater + Jeans + Boots

When I put this outfit on, I knew immediately it would be my cold weather uniform. It just feels like me. I can swap my favorite pair of lug sole boots or tall boots for different looks. Below I am wearing my rag & bone Shawn Chelsea boot that I picked up last year and love, love, love. I am willing to spend more on a pair of black boots, which I know I will own for years to come.

My sweater is the Eileen Fisher Funnel-Neck Boxy Sweater that I picked up at Nordstrom on recommendation from Shana at The Mom Edit.  I am definitely a fangirl of TME. My goal when I grow up is to write like Shana. Yes, I am aware I am much older than her. I would love StyleDahlia to be the midlife, empty nest TME! We all got to have goals! Xoxo Shana.

But back to the sweater, I initially purchased the S/M, which is sold old, but I felt it was a bit short.  The L/XL is a similar fit to the S/M but with a longer length, which this tall girl absolutely needs.

I plan to dress this sweater up for the holidays with the ATM Silk Joggers, currently 50% off at Nordstrom, or the Diandra Pleated joggers from my How to Style Satin Joggers post. I just reordered in a size smaller (6T) and are now on sale for under $50.

Over 50 women wearing plaid flannel shirt, sweater, jeans and boots

Outfit #4: Flannel Shirt + Body-Con Dress + Boots

This James Perse Classic V-Neck Skinny Dress is an MVP of my wardrobe. It is 4-5 years old and still looks great. It is a perfect canvas for building outfits. I love it so much I devoted an early blog post to The LBD You Need in Your Wardrobe. It is figure flattering and forgiving and therefore works with all bodies.

Many brands have tried to replicate this dress, including the Leith Ruched Dress that many people love.  I have found the James Perse dress to be the only body-con dress I can wear without an additional smoothing garment. It is currently almost sold out, but it is a staple of the brand and is usually restocked every year.

My boots are the Stuart Weitzman Lowland, which I recently picked up at Tradesy. I have the same boots in black, which I wear all the time, but I wanted a color I could wear with black dresses. These boots are expensive, but I could save almost $300 by buying them on Tradesy.

They are a never worn pair in the popular Toppo color that I have been looking for everywhere. A note on sizing the Lowland boots – I wear an 8.5 in almost all boots and rarely a 9, but it does happen occasionally, but in these boots, I am a size 8. They run large. So I suggest you try them on before purchasing from a resale site. Tradesy has a great return policy, but not all of them do.

To get the blousing effect in my second photo, add a belt tight around your middle and then pull up the shirt to hide the shirttails and the belt for a loosely tucked shirt effect. It is a common trick of Instagram influencers. You can use this trick on shirts and sweaters layered over your favorite skirt or dress.

Outfit #5: Flannel + T-Shirt + Jeans + Sneakers

When you think flannel shirt outfit, this is likely the first thing that comes to mind. In CA, you can easily wear a flannel as a shacket over your favorite tee.  I went with a plain white tee, but add your favorite graphic tee for a more rock n’ roll look. When the weather gets hot, tie the flannel around your waist. You will likely see me sporting this outfit all over town.  Any day I can get away with wearing sneakers, I do!

Midlife women wearing flannel shirt, white tee, jeans and sneakers

Outfit #6: Flannel Shirt + Velvet Pants + Heels + Sparkle

Our prospects for group celebrations for the holidays seem remote but intimate gatherings are still an important way to celebrate. This year instead of going all out on a new party outfit, I am shopping my closet for festive outfits for all of my small gatherings.  I mentioned earlier that my shirt had a Christmas plaid feel, so I added velvet pants, heels, and some fun bling jewelry to dress it up for the holidays.

Instead of lugging my big everyday purse, I swapped it out for a beaded clutch. I added my go-to fancy hoop earrings that go with absolutely everything and one of my MIL’s vintage rings for a little more sparkle. If you are feeling daring or meeting in the evening, you could wear your shirt unbuttoned a bit more and have your favorite lace bralette peeking out. I like the Free People Adella Long Line Bralette.

Midlife women wearing plaid flannel shirt, velvet pants and sequin purse.

Midlife women wearing plaid flannel shirt, velvet pants and sequin purse.

2020 has thrown us all for a loop. The modernizing of grunge is the logical fashion response. The trend is based on comfort and wearability. A plaid flannel shirt is a cozy addition to any wardrobe with so many possibilities for styling, even if the only place you end up wearing it this year is at home in front of the fire. It has been 27 years since my last drink, and I am not missing the Grunge trend this time.

I would love it if you followed me on Instagram for my everyday outfits or on Pinterest for my fashion inspiration. StyleDahlia is a fashion and lifestyle website with a modern take on midlife. We hope to inspire you to step out of your comfort zone, try new things, and live your life in full bloom.

 

 

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StyleDahlia is a fashion and lifestyle blog with a modern take on midlife. We celebrate the beauty in everything whether it be fashion, travel, or home. StyleDahlia offers and honest take on aging, fashion and everyday. Our hope is to inspire you to see beauty in the little things, step out of your comfort zone, try new things, and live your life in full bloom.

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