How to Style an Oversized Flannel Shirt

In today’s post, I’ll show you how to style an oversized flannel shirt without looking grumpy.

Flannel shirts aren’t plaid shirts, but the fact that most flannel shirts are plaid is making the misconception a bit too common. Plaid or non-plaid, it’s hard to disprove the fact that flannel shirts are simply chic.

A trend that has been picking up heat in recent times is that of ladies styling oversized flannels.

While it’s pretty easy to find dresses that work well with flannels, it’s also easy to find those that don’t. Here are some outfit ideas that show how to style a flannel shirt to look your best on your next outing.

How to Style an Oversized Flannel Shirt

Table of Contents

1. Plain Turtle-Neck Tee with Oversized Flannel Shirt + Ripped Jeans + Boots + Sweat Cap

This is about the best way to style an oversized flannel shirt with a plaid pattern, no doubt. The sweat cap compliments the outfit perfectly and the cute smile makes her ready to go. Copy that if you can.

Plain Tee + Oversized Flannel + Ripped Jeans + Boots + Sweat Cap

2. Black Tank Top with Oversized Flannel Shirt + Jean Shorts + Sandals

Here is another great outfit idea with flannels. This is best for night-outs and other informal gatherings, as you don’t want to wear something like this to work. The way you wear the flannel shirt should depend on the temperature; it’s warm in this picture, I guess.

Black Inner Shirt + Oversized Flannel + Jean Shorts Sandals

3. Well Buttoned Oversized Flannel Shirt with Thigh-High Boots + English Hat

What about wearing your oversized flannel without anything significant underneath. This is exactly what she does here, and it seems to work. These thigh-high boots and the English hat give her a semi-cowgirl look, but it’s still excellent.

Well Buttoned Oversized Flannel + Thigh High Boots English Hat

4. Graphic Crop Top with Oversized Flannel Shirt + High Waist Leggings  + Sneakers

You shouldn’t expect anything to go wrong with an outfit, as long as a white graphic top is matched with black leggings. Since this outfit fulfills that requirement, it’s only natural that it looks extraordinarily elegant.

Graphic Crop + Top Oversized Flannel + High Waist Leggings Sneakers

5. Oversized Flannel Shirt with Thigh-high Boots + Sunglasses + Chic Bag

Here’s another oversized flannel idea without any significant outfits underneath. It looks like something you should wear to a night out and the match between sunglasses and the boots is surreal.

Oversized Flannel + Thigh-high Boots + Sunglasses

6. Buttoned Up Oversized Flannel Shirt with Ripped Jeans + Converse Shoes

Depending on how you typically dress, you may not acknowledge that this qualifies to be called an oversized flannel. Nonetheless, you’ll agree that it looks chic and is something worth going out of your way to copy.

Buttoned Up Oversized Flannel + Ripped Jeans + Sneakers

7. Turtle Neck Shirt with Flannel Shirt + Jean Pants + Boots + English Hat

Turtle neck tops and jeans have always worked well together, but why not add a flannel shirt to make it even better. If the boots were a bit bigger, she’d have passed for an alluring cowgirl.

Turtle Neck Shirt + Jeans Pant + Boots + English Hat

8. White Tee with Oversized Flannel Shirt + Ripped Black Jeans + Combat Black Boots

This outfit consists almost entirely of whites and blacks, and it’s no surprise that it looks chic. If you’re dressing like this to work, however, you may want to remove the sunglasses to retain a professional look.

White Tee + Oversized Flannel + Ripped Black Jeans + Knee-high Boots

9. Crop Top with Oversized Flannel Shirt + Loose-fitted Jeans + Boots

Wearing oversized flannels over crop tops makes the outfit looks a bit more conservative, but it doesn’t really make it less fashionable. Simply take a look at the outfit below and try not to copy it; spoiler: you can’t.

Crop Top + Oversized Flannel + Loose-fitted Jeans + Boots

10. Black Inner Tank Top with Oversized Flannel Shirt + Sweat Shorts + Shoes

If you’re going over to a friend’s house for a movie there’s really no point in an ultra-sophisticated dress. Dress in a simple black top and sweat shorts for a liberating experience. However, replicating that smile would be slightly more complicated.

Black Inner Top + Oversized Flannel + Sweat Shorts + Sneakers

11. Well Buttoned Oversized Flannel Shirt with Leather Pants + Shoes

A well-buttoned flannel and leather pants combine excellently, and you don’t even need any extra clothing. The fact that the entire outfit, including the sneaker, is either black or white also makes it better.

Well Buttoned Oversized Flannel + Leather Pant + Sneakers

12. Well Buttoned Oversized Flannel Shirt + Boots + Handbag

Who says you need an extra piece of clothing to style an oversized flannel. As the model demonstrates below, the flannel is enough to cover everything that needs covering, with the boots and the handbag doing the rest of the job.

Well Buttoned Oversized Flannel + Boots + Handbag

13. Black Top + Oversized Flannel Shirt + Leggings + Boots + English Hat

This is the plaid flannel equivalent to an all-black outfit since it seems like all-blacks flannels don’t exist. I’m struggling to think of a scenario where this outfit will look out of place, can you help?

Black Top + Oversized Flannel + Leggings + Boots + English Hat

14. White Crop Top + Oversized Flannel Shirt + Light Blue Jeans + Sneakers + Sunglasses

Crop tops are excellent with jeans, but this model just proved that wearing supersized flannels over them isn’t a bad idea either. It’s important to avoid buttoning the flannel since the color should match with that of the sneakers.

Chic Crop Top + Oversized Flannel + Mums Jeans + Sneakers + Sunglasses

15. Black Top + Oversized Flannel Shirt + Joggers + Sneakers + Handbag + Sunglasses

Here’s another outfit that should’ve been all-black, if all-black flannels existed. Since there aren’t any, we’ll have to make do with this simple chic outfit. The sunglasses make her look kind of like an FBI agent in my opinion.

Black Top + Oversized Flannel + Joggers + Sneakers + Handbag + Sunglasses

16. Oversized Flannel Shirt with Belt + Black Shoes

This flannel can easily be mistaken for a short dress due to its massive size. The belt at its waist is also perfect for masking what it actually is, but that doesn’t matter. As long as you can get one of these patterns and an equally alluring smile, copying the look is easy.

Belted Oversized Flannel + Sneakers

17. Inner Vest + Oversized Flannel Shirt + Leggings + Knee-High Boots

The flannel may not be massively oversized, but it does a good job of representing the outfit idea the model is trying to get across. Notice how the boots look like a dull version of the inner vest’s color; that’s another important part of the outfit.

Inner Vest + Oversized Flannel + Leggings + Knee-High Boots

18. Oversized Flannel Shirt + Leggings + Thigh-high Boots

As evidenced by several outfit ideas above, you don’t need anything under your plaid-patterned flannel to look amazing. Take a look at her for example; while the boots seemed excessive, nothing really seems off about her outfit.

Oversized Flannel + Leggings + Thigh-high Boots

19. Black Crop Top with Oversized Flannel Shirt + Ripped Jeans + Boots + English Hat

With a hat, a casual dress, and a pair of boots, this model captures the cowgirl look perfectly. Of course, you won’t want to wear this in a professional environment; strictly vacations only!

Black Shirt + Oversized Flannel + Ripped Jeans + Boots + English Hat

20. Basic Jumpsuit + Oversized Flannel Shirt + Sneakers

Jumpsuits are basically made to be convenient and comfortable, and there’s nothing that screams comfortable better than this outfit. Adding a flannel over the jumpsuit only makes it as chic as she looks in the outfit.

Basic Jumpsuit + Oversized Flannel + Sneakers

21. Sweat Shirt + Oversized Flannel Shirt +Gray Jeans + Boots

Who says flannels aren’t meant for fashion? Obviously, they haven’t seen this extraordinary outfit idea. The match between the color of the sunglasses and the boots is also sick, bringing the whole outfit together.

Sweat Shirt + Oversized Flannel +Gray Jeans + Boots

22. Buttoned Up Oversized Flannel Shirt + Leggings + Knee-high Boots + Handbag

This flannel looks more like a plaid shirt, making it perfect with leggings and a pair of knee-high boots. While I think matching the colors of the boots and the handbag will work better than using a different color.

Buttoned Up Oversized Flannel + Leggings + Knee-high Boots + Handbag

23. Graphic Tee + Oversized Flannel Shirt + Tight Shorts + Sneakers

Maybe it’s just impossible for graphic tees to look bad at this point, since they always look awesome, regardless of the footwear or culotte choice. Get a pair of sneakers that match the flannel and complete the outfit, recreating her look.

Graphic Tee + Oversized Flannel + Tight Shorts + Sneakers

24. Oversized Flannel Shirt + Black Tee + Joggers + Sneakers + Handbag

Every part of this outfit looks cohesive, maybe because the colors were strategically chosen to match. Note the match between the sneakers and the handbag, as well as that of the sunglasses and the tee.

Oversized Flannel + Black Tee + Joggers + Sneakers + Handbag

25. Graphic Tee + Oversized Flannel Shirt + Skinny Pant +Boots + Sweat Cap

We’ve talked about graphic tees several times earlier and they work like magic if you get the colors right. In this scenario, it seems like she got the colors and you can see how cool the result is for yourself.

Graphic Tee + Oversized Flannel + Skinny Pant +Boots + Sweat Cap

And that’s all for my post on how to style an oversized flannel shirt. Want some more outfit ideas? Then you might want to check out these blog posts.

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How to Style an Oversized Flannel Shirt