How to Wear a Flannel Shirt for Fall

My absolute favorite print (next to leopard) is plaid for all seasons. I own so much that I cannot do all of the outfits in one blog post. This is the second installment in my plaid marathon as we focus on how to wear a flannel shirt for fall (or winter). In this look book I have a total of 22 outfits that go all the way back as far as six to seven years. I try to collect different colors of long sleeve plaid shirts, then I find creative ways to style them. Besides getting totally inspired by each outfit, I have pieces that you can shop now to copy my outfits.

New this year on the blog I started showing my outfits on my mannequin, as well as on myself and in a flat lay. I did a poll on my Instagram stories asking you all if I should continue with the mannequin or stop. The reason that I ask is that it takes an excruciating amount of time to do the mannequin photos, which is entirely a waste if they are not adding any value. The results were split about 40% keep to 60% ditch. I view that as the mannequin is take it or leave it for you all. Of course, please share your thoughts in the comments. For this post I am not doing the mannequin.

Look #1: Country red plaid

The first outfit as I showcase how to wear a flannel shirt for fall has a country vibe. The light blue shades in the red plaid shirt jive well with these “retro” jeans with slight ribbing. My booties play into the country feel, and fringe is never a bad idea. The gold multi hoop earrings add a touch of class and glamour. I want to do something different with the handbag from the usual, so why not a small red bag? It is always important to me that the shades of red match.

Shirt: No Boundaries from Walmart
Jeans: YMI from Gabe’s
Handbag: No Boundaries from Walmart
Booties: Faded Glory from Walmart
Earrings: Romeo & Juliet from Gabe’s

Featured | Tie Front Plaid Flannel Shirt + Stretch Straight-leg Boyfriend Denim Jeans + Leather Top Handle Satchel + Dingo Jerico Booties + Multi-layer Hoop Earrings

Look #2: Fall hues plaid

Second, this outfit features the shades of fall and screams pumpkin spice. The plaid shirt blends mustard yellow and rusty orange in a beautiful way. You will notice that the rust pants match the stripes in the shirt perfectly and really pull that hue out. I am using a mustard handbag to also pull that hue out of the shirt and to provide balance. Brown boots (although black are ok, too) compliment the fall tones appropriately. I like gold jewelry to go with these colors.

Shirt: No Boundaries from Walmart
Pants: Shirt: No Boundaries from Walmart
Handbag: Shirt: No Boundaries from Walmart
Boots: Wear Ever from Peebles
Necklace: Time and Tru from Walmart

Featured | Button Down Flannel Shirt + Cotton Blend Jegging + Knee High Riding Boots + Simple Shoulder Crossbody + Sideways Initial Necklace

Look #3: Purple and blue plaid

Third is an attitude-packed look. I am working with the purple and blue in the shirt by pairing it with a matching purple and blue druzy necklace. To break up the black in the shirt, but to compliment the gray, I am opting for black acid wash jeans. Combat boots work with any attitude outfit, but the heels are a nice added touch. The studded handbag is a why not? piece. It works with the leather of the boots and the overall aesthetic to add interest to the eye.

Shirt: Shirt: No Boundaries from Walmart
Jeans: Vanilla Star from Sears
Boots: Attention from Kmart
Handbag: Madison and Mallory
Necklace: Kmart

Featured | Long Sleeve Plaid Shirt + Acid Wash Black Jeans + Soda Malia Combat Boots + Druzy Stone Pendant Necklace + Rivet Chain Handbag

Look #4: Rockstar plaid

Fourth is an outfit that is near and dear to my heart, and falls into the “old” category from six or seven years ago. This outfit has transformed a bit throughout the years, but the basic building blocks are still here. I used to wear this with distressed black pants covered in jewels, but they no longer fit. This outfit inspired me to start this blog. It cannot be skipped in how to wear a flannel shirt for fall. I recall photographing myself in this outfit many years ago when I felt the calling to start blogging, but I did not start at that moment.

Anyway, I like to wear this shirt open for something different. Most plaid shirts are highly versatile, whether you wear them fully buttoned, unbuttoned, or partially buttoned. I wear a solid black cami to fill the open space, then throw on some super distressed jeans for ultimate attitude. Studded boots are a must with this rockstar style. The star of the show may just be the chunky sideways cross necklace on that thick chain. I am adding the bling back in with a gem-studded faux fur clutch, which is one of my all-time favorite bags.

Featured | Button Down Plaid Shirt + Solid Cami Top + Distressed Skinny Jeans + Sterling Silver Sideways Cross Necklace + Faux Fur Handbag + Chelsea Ankle Boots

Look #5: Teal plaid

Fifth in how to wear a flannel shirt for fall is a lovely teal style. I like to also wear this shirt open and allow the crochet back to flow freely. The leggings have a faux leather racing stripe that make them anything but ordinary. As you will see a lot, styling plaid shirts in an attitude-filled or gothic way is my favorite way to do it. The layered necklaces give something back to the neck area. Leather handbags with grommets are always a great choice with these types of outfits. The studded booties are making an appearance again, as they will several times.

Shirt: No Boundaries from Walmart
Black cami
Leggings: No Boundaries from Walmart
Crossbody: No Boundaries from Walmart
Booties: Charles Albert from Delias
Necklaces: Walmart

Featured | Roll Up Long Sleeve Plaid Shirt + Solid Cami Top + Black Buttery Soft Leggings + Wolf Tooth Tribal Pendant Necklace + Small Studs Crossbody + Chelsea Ankle Boots

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Related Post: Best Women’s Hats for Fall | Staples

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Look #6: Classic red plaid

Next is a basic red plaid look. Red plaid is my favorite color for flannel, and this time I am wearing it with slightly distressed black jeans for something different. I evidence here how versatile the studded booties are. The jewelry does not need to be anything over the top here, as a simple elephant pendant is enough. I love a good distressed leather bag when I want to look grungy.

If you are wondering why some of these outfit pictures are low quality and/or sized funny, I am using my original flat lays that I shot years ago.

Shirt: No Boundaries from Walmart
Pants: No Boundaries from Walmart
Crossbody: No Boundaries from Walmart
Choker: Walmart
Booties: Charles Albert from Delias

Featured | Roll Up Long Sleeve Plaid Shirt + Ripped Stretchy Skinny Ankle Jeans + Elephant Pendant Necklace + Rivet Hobo Bag + Chelsea Ankle Boots

Look #7: Purple plaid

It does not get any more simple when it comes to how to wear a flannel shirt for fall. This is for my purple lovers! Grab your favorite purple plaid shirt and throw it on over a pair of black jeans. The shirt has a lot going on, so I prefer earrings with this outfit, but in a matching shade of purple. You will see that the faux fur handbag is slightly darker, but it ties the entire outfit together well.

Featured | Long Sleeve Button Down Flannel + Nora Skinny Fit Pull On Jean + Faux Fur Messenger Bag + Chelsea Ankle Boots + Amethyst Cluster Earrings

Look #8: Half and half

Continuing on, I have a unique shirt. Remember how I said red plaid is my favorite? My second favorite is black and white, so this shirt is amusingly me. To keep the grunge going, I am wearing this flannel with solid black pants with distressed knees. The bull bar handbag is a nice touch with this attitude theme (are you sick of this word yet?). I am finishing the look with studded booties and a layered choker.

Shirt: rue21
Pants: No Boundaries from Walmart
Booties: London Rag from Peebles
Purse: No Boundaries from Walmart
Choker: Walmart

Featured | Pocket Front Spliced Plaid Blouse + Slit Knee High Waisted Jeans + Studded Buckle Ankle Boots + Leather Wrap Choker + Black Clip Pouch Purse

Look #9: Gray plaid

Here is a gray plaid look! This shirt has spike studs on the pockets, which means I need to play with that feature. There are studs on the gray denim handbag that matches the outfit so well. I can bring back the black distressed knee pants again and they are appropriate here. The hoops are more of a gunmetal, but the fringe composed of crystals and chains speaks to me with the stud theme. Finally, there are studs on the booties, too.

Shirt: Dizzy Lizzy from Peebles
Jeans: No Boundaries from Walmart
Booties: London Rag from Peebles
Crossbody: Walmart
Earrings: Walmart

Featured | Roll Up Long Sleeve Plaid Shirt + Small Denim Vera Tote + Chain Hoop Earrings + Studded Buckle Ankle Boots + Distressed Skinny Jeans

Look #10: Layered black and burgundy plaid

Pressing on with how to wear a flannel shirt for fall, I have a layered look that is totally a style hack! The plaid shirt came with the cami as a matching two-for-one, so we just need to accessorize the rest. Basic blue jeans are great here, but I am bringing the black back in with the wedge heel booties. This look needs a bit of shine, which I achieve with the attention-grabbing earrings. Finish the style with that grommet handbag.

Shirt two for one: No Boundaries from Walmart
Jeans: Bongo from Sears
Booties: Time and Tru from Walmart
Crossbody: No Boundaries from Walmart
Earrings: Walmart

Featured | Roll Up Sleeve Flannel Shirt + Criss Cross Strappy Cami + Wedge Heel Booties + Gold Label Modern Skinny Jeans + Multi-chain Hoop Earrings + Small Studs Crossbody

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Related Post: Preppy School Girl Outfits | 3 Looks

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Look #11: Infinity scarf plaid

Next is a comfy style for my red plaid lovers. This basic shirt pairs well with soft leggings for a casual outfit. A scarf will keep you extra warm and toasty. Do you just feel like wearing knee-high boots with leggings? Me too, and leather boots always work well with plaid. For something different, I am bringing back the concept of “arm candy” and accessorizing with my favorite bracelets for stacking. The finishing touch is lip handbag, simply because I can.

Featured | Gingham 3/4 Sleeve Top + Light Weight Infinity Scarf + Over the Knee Riding Boots + Stackable Bracelets + Lips Evening Bag + Black Buttery Soft Leggings

Look #12: Lace-up plaid

Here is another easy look. I am really incorporating textures here, which I love to do with outfits, because that makes them look more “expert” without trying. This tie front red plaid shirt is a little bit different, but I like how it looks with faux fur leggings. For more texture, I have suede knee high boots and a fringe handbag. I am accessorizing this outfit with dangle spike earrings because they scream grunge and goth.

Shirt: Poly & Ester from Ross
Crossbody: Walmart
Leggings: Joe Boxer from Kmart
Boots: Groove from Delias
Earrings: Kardashian Collection from Sears

Featured | Lace Up Plaid Shirt + Faux Leather Leggings + Fringe Tassel Bag + Suede Over the Knee Boots + Black Spike Earrings

Look #13: Burgundy plaid

Are you a burgundy lover like me? You are going to die for this one! This burgundy plaid shirt matches the pants perfectly for a color-on-color look that is totally safe and tasteful. The ribbon choker matches the tie front laces well, but I am also layering with a silver pendant necklace to match the silver o-rings. We are missing grungy leather with this look, so here comes that distressed leather bag, and some simple black riding boots.

Shirt: No Boundaries from Walmart
Pants: Jordache from Walmart
Boots: Rampage from Peebles
Crossbody: No Boundaries from Walmart
Chokers: Five Below and JCPenney

Featured | Lace Up Front Plaid Shirt + Ultra Stretch Skinny Pants + Noble High Riding Boots + Silk Ribbon Choker + Rivet Hobo Bag

Look #14: Blue plaid

This blue plaid shirt is incredibly long on me, more like a tunic, so the way that I compromise is to wear it over leggings. The overall length of the shirt compliments knee high boots well. Gold accents look stellar with this shade of blue, so I am incorporating them with the long necklace and the handbag. Notice the handbag is patent, which adds another layer of texture.

Shirt: Davi & Dani from Madison and Mallory
Black leggings
Boots: Charles Albert from Delias
Handbag: Burlington
Necklace: Time and Tru from Walmart

Featured | Long Sleeve Plaid Tunic + Clear Crystal Necklace + Faux Patent Handbag + Black Buttery Soft Leggings + Noble High Riding Boots

Look #15: Layering with plaid

Add this next outfit to your list on how to wear a flannel shirt for fall as I showcase how to layer! I have this super fun black and white graphic tee, which works perfectly with this black plaid shirt. Now I have an excuse to play with black and white to my heart’s content, so here come my black and white booties. The graphic tee has a lot going on, so I am accessorizing with a choker that brings the missing bling back. The black jeans feature mild distressing and zippers, which are great for this grunge look. Finish this outfit off with a leather bucket bag.

Shirt: Joe Boxer from Kmart
T-shirt: Ross
Pants: Adam Levine from Kmart
Booties: Mari A from Madison and Mallory
Purse: No Boundaries from Walmart
Choker: rue21

Featured | Selena Black & White Portrait Shirt + Dillon Classic-fit Flannel Shirt + Ripped Distressed Skinny Jeans + Bucket Bag + Pointed Toe Chelsea Boots + Layered Black Leather Choker

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Related Post: Best Women’s Hats for Fall | Staples

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Look #16: White and gray plaid

I find this white and gray plaid shirt to be a style challenge, but it really came together. Here I am exploring how an ashy light gray can work with taupe and live in harmony. The layered necklace set has gray stones that match the shirt perfectly. Medium wash jeans work with the overall color scheme. The taupe comes in with the handbag, belt, and bootie combo. If you look closely at the buttons on the shirt, you can see flecks of taupe, which is really how I get away with this entire outfit.

Shirt: Hayden from Madison and Mallory
Jeans: YMI from Peebles
Booties: Faded Glory from Walmart
Belt: Madison and Mallory
Necklaces: Time and Tru from Walmart
Handbag: Ross

Featured | Gray Plaid Rocky Button-Down + Kiss Me Skinny Jeans + Double Circle Belt + Layered Medallion Necklace + Medium Crossbody Bag + Dingo Jerico Booties

Look #17: Mustard and black plaid

For more layering inspiration, here I am wearing a mustard plaid shirt over a black bodysuit. I am leaving the shirt open so that the bodysuit and the layered necklaces can be seen. Gold accents look best with mustard every time. Yellow and black is the running theme here, hence the black wedge heel booties are back. I cannot resist grabbing my mustard handbag with these types of shirts. The blue jeans are super vibrant, but they are best friends with the mustard hue.

Shirt: No Boundaries from Walmart
Bodysuit: No Boundaries from Walmart
Jeans: No Boundaries from Walmart
Handbag: No Boundaries from Walmart
Booties: Time and Tru from Walmart
Necklaces: Madison and Mallory

Featured | Buffalo Plaid Flannel Shirt + Round Neck Short Sleeve Bodysuit + Layered Pendant Necklaces + Simple Shoulder Crossbody + Wedge Heel Booties + Gold Label Modern Skinny Jeans

Look #18: Mustard plaid

Can you tell that I like mustard a lot? This shirt is a bit more elegant than the latter. I love how it looks partially tucked in with a complimentary belt. Standard blue jeans work with the striping on the shirt. Layered necklaces are never a bad idea. A round handbag is a breath of fresh air, but it adds fabulous leather texture along with the suede booties.

Shirt: Lush from Madison and Mallory
Jeans: Bongo from Sears
Booties: Time and Tru from Walmart
Necklaces: Madison and Mallory
Belt: Madison and Mallory
Handbag: A New Day from Target

Featured | Button Down Plaid Shirt + Soft Faux Leather Belt + Nylon Circle Crossbody Bag + Layered Pendant Necklaces + Wedge Heel Booties + Gold Label Modern Skinny Jeans

Look #19: Red, white, and blue plaid

My blue velvet combat boots are super unusual, yet they are one of my favorite pairs of shoes, and this outfit is dedicated to them. The lace-up front shirt matches the blue in the plaid shirt perfectly, so I am using it as a layering piece. I like to allow the sleeves to peek out from the plaid shirt. Rich blue jeans are a nice contrast from the lighter blue. I am finishing the look with an attitude handbag and earrings that will not interfere with everything we have going on.

Shirt: No Boundaries from Walmart
Jeans: Kayden.x from Ross
Long sleeve shirt: No Boundaries from Walmart
Booties: Joe Boxer from Walmart
Earrings: Claire’s
Crossbody: rue21

Featured | Criss Cross Shirt + Classic Plaid Shirt + Round Toe Combat Boots + Screw Stud Earrings + Gold Label Modern Skinny Jeans + Black Clip Pouch Purse

Look #20: Punk plaid

Next in how to wear a flannel shirt for fall is one of my all-time favorite outfits, plus I love how the photos came out! When it comes to fashion I live for how it gives the ability to be whoever you want to be that day. You would swear that I am a grunge or goth person who dresses this way every day, but that is not true! Playing dress-up is what I do.

A great way to wear shorts in colder months is to layer them with tights, which also happens to be super grungy. I am leaving the green plaid shirt open so that the graphic tee can be clearly read. Tying the shirt up adds an extra touch, while deviating away from simply tucking it in or doing nothing with it. A fringe crossbody gives us some texture, and I cannot skip the studded booties here. Tattoo chokers are absolutely a classic, but it needs a little bit more, hence the reason why I am layering it with a silver pendant necklace. Notice the shorts are incredibly dark blue to help break all the black up.

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Related Post:Preppy School Girl Outfits | 3 Looks

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Featured | Roll Up Plaid Shirt + Nope Graphic Top + Distressed Short + Sheer Control Top Tight + Tattoo Choker Set + Fringe Tassel Bag + Chelsea Ankle Boots

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Related Post: How to Style a Plaid Shirt – 10 Ideas

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Look  #21: Goth plaid

The cat face shirt is actually a Halloween shirt, but that will not stop me from layering with it anytime. The cat’s eyes compliment the olive green plaid shirt well, which I am wearing open so that you can see the cat. Black acid wash jeans break all the dark colors up, but they also match the cat face. Suede knee high boots are a match made in heaven. Notice the fringe tassels on the boots correspond with the leather backpack, which is the ultimate punk statement piece. The final piece is a cross pendant choker, which is a classic staple in any goth wardrobe.

Shirt: Poly & Esther from Ross
Cat tee: Walmart
Jeans: Vanilla Star from Sears
Boots: Attention from Kmart
Backpack: No Boundaries from Walmart
Choker: Walmart

Featured | Black Cat T-shirt + Soft Flannel Essential Shirt + Over the Knee Chunky Heel Boots + Velvet Cross Pendant Choker + Studded Leather Backpack + Acid Wash Black Jeans

Look #22: Black and white plaid

We are now at the final outfit in how to wear a flannel shirt for fall. Can you believe it? Thank you for sticking with me through this long post! Layering with plaid is so much fun that I am doing it one more time. This black and white plaid shirt blends hues into a gray look, which works well with a heather gray graphic tee. Both shirts are rather light, so I can get away with black jeans here. It is time for texture play, as we have flannel, and now leather boots and a faux fur handbag. Chunky necklaces with punk pendants bring the entire outfit together like the cherry on top.

Featured | Soda Zulu-s Boot + Button Down Plaid Shirt + Graphic Tee + Triangle Pendant Necklace + Nora Skinny Fit Pull On Jean + Faux Fur Handbag

Conclusion

We have now made it through all 22 outfits in how to wear a flannel shirt for fall! To summarize, plaid presents an amazing opportunity to dress as grunge/punk/goth/attitude filled as you want. Of course, you can make these outfits sugary and sweet if you want to. Plaid or flannel shirts are not just for keeping you warm, rather, you can experiment with how you layer, mix, and match them. Consider playing with the buttons, adding in different textures to your look, or maybe throw on a belt or a fedora. Other details like lace-up or tie front shirts are also nice. You can transform any button-down shirt into a tie front simply by leaving the last few buttons unbuttoned! By now, you should be oozing with inspiration. More plaid outfits are on the way! Until next time, continue to let your true beauty shine.

How do you style plaid?

View More of the Plaid Outfit Series:

Plaid Pieces for Fall	Plaid Kimono Outfits	Plaid Shirt Ideas
Plaid Tunic Outfits	Preppy School Girl Outfits	Summer Plaid Outfits