You probably already know that flare jeans, also known as bell-bottoms, were worn by hippies and rockstars in the 1960’s and 1970’s— but did you know that they were originally worn by sailors in the Navy?! I love fun facts and the history of fashion, I always find them so interesting! The fashion industry is cyclical in nature and things come in and out of style and back in again— flared jeans being no exception!

I like the exaggerated silhouette of flare jeans. They seem to make your legs look longer, and balance out your shape if you are pear-shaped (like me). It has been awhile since I have worn this style of jeans, but I brought this cut back into my wardrobe this year. For size reference, I am 5’7″and I got the jeans worn throughout this post in my true size, but ordered the long inseam. Here are five outfits combinations that I will be wearing this fall, made with flare jeans!

5 Fall Outfits with Flare Jeans

Outfit #1: Button-down Shirt + Loafers

Shirt (old – similar, similar, similar – all from the same brand) | Jeans | Loafers (old – similar from the same brand)

This outfit feels like an everyday look to me. It feels a bit elevated because of the shape of the flare jeans with the pointed-toe loafers and tailored shirt. However, the flannel material of the shirt and the mid-blue color of the denim makes it feel casual as well. I would wear this for everyday activities, but I also would wear this to a get together with friends or out on a casual date night.

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Outfit #2: Turtleneck Sweater + Slip-On Sneakers

Sweater (old from Madewell – similar, similar, similar) | Jeans | Earrings | Sneakers

I love this outfit because it is super comfortable and has a lot of visual interest. This sweater is soft and warm and the turtleneck shape pairs well with the flare jeans. The color and texture of the sweater bring visual interest to the outfit and so do the checkered slip-on sneakers. This is an everyday outfit which can be easily elevated by swapping out the sneakers for boots.

Outfit #3: Blouse + Jacket + Boots

Blouse (sold out – similar in white from the same brand) | Jacket | Earrings | Jeans | Boots ( old – this year’s version) | Belt Bag (same one in matte material)

This outfit feels the most like a date night or night out with the girls sort of outfit. I love juxtaposition in outfits like the dark, thick faux leather material against the light, airy blouse. I like to mix hard and soft, as well as feminine and masculine styles when making outfits.

Outfit #4: Long-sleeve Shirt + Cardigan Sweater + Boots

Shirt | Sweater (old – similar same brand) | Bag | Jeans | Boots (old – new version)

This is another everyday look. I love the color combination in this outfit— the blue denim with taupe boots, cream top, rust sweater and cognac tote all feel so fall-ish together. I love texture and I have worked it into this outfit in both the top and the sweater.

Outfit #5: Oversized Graphic Tee + Sweater + Mules

Graphic Tee (sold out – similar, similar) | Earrings | Jeans | Sweater (old) | Mules

This last outfit is casual and feels retro with the oversized band tee. I added woven mules and a fuzzy sweater for more texture. I would wear this as an everyday outfit for daily activities.

Thanks for reading this post! If you are interested to know what other jeans I am wearing this fall, check out this post about all of my fall denim plus my denim wish list!

What about you, are you a fan of flare jeans? What are your favorite styles of denim right now? I would love to hear from you in the comments below!