Casual Fall Outfit Ideas With Jeans

September 14, 2021

Casual Fall Outfit Ideas with Jeans

I have to say, I am so glad jeans have returned to my life this year. No doubt I spent weeks (maybe months?) not wearing them due to the pandemic shelter in place order but I have to say I missed my jeans collection! I know it’s hard to motivate ourselves these days so if you’re feeling uninspired lately when it comes to getting dressed – this post is for you! Lots of cute outfit ideas coming your way for the fall season.

Sophie Blazer I wit & whimsy

Casual Fall Outfit Ideas with Jeans

Casual Fall Outfit Ideas With Jeans

Jeans are of course a staple of my wardrobe year round but even more so in Fall when I start to wear darker washes along with my classic blue jeans. I also am a fan of wearing white jeans in the Fall with white sweaters! I always love a monochromatic look and never tire of casual wear looks featuring jeans.

As we know jeans are so versatile. You can dress them up with a great pair of heels and a dressier top, you can wear them with the most casual of pieces like hoodies and sneakers and you can have them be perfectly casually cool when worn with the right accessories or more tailored pieces.

Today’s post is filled with Fall style ideas – reliable casual outfit ideas on how to wear your casual jeans this Fall and many of these could also be translated and styled for winter outfits, too. Read on for plenty of cute Fall outfits!

Casual Fall Outfit Ideas With Jeans

Casual Fall Outfit Ideas With Jeans

The Jean That Can Be Business Casual

The most flattering jean ever – this one is high rise and perfectly tailored to pair with more business casual, work outfits. They also look great with a timeless pump. Wearing: Agolde Nico Jeans in size 27.

And is there anything better than a jean paired with a plain white tee? A forever combo that’ll always be in style.

This jean is great for wearing with blazers and more refined jackets as seen here:

Casual Fall Outfit Ideas With Jeans

Meghan Donovan of Paris, Perfected

Next up we have some color…

Casual Fall Outfit Ideas With Jeans

The White Kick Flare Jean

White jeans are not just for summer fashion in my opinion! These Kick Flare white jeans with distressed hems are a favorite of mine all year round. Wearing: Velvet Twiggy Jeans in size 28.

And don’t forget the white skinny jeans, too!

Everlane White Jeans

Wearing: Everlane Authentic Stretch High Rise Skinny in size 28.

Read Everlane Denim Guide.

Maison Scotch Stripe Coat I Stuart Weitzman Lowland Boots

Jeans with Knee High Boots or Over the Knee Boots

Always a sleek outfit – add your favorite flat or heeled knee high boots or over the knee boots.

J.Crew Sweater Blazer Styling Ideas I wit & whimsy

Distressed Vintage Straight Jeans

These jeans fill lived in right away. They have a vintage vibe to them and some distressing perfect for casual or weekend wear outfits. Wearing: Madewell The Perfect Vintage Jean in size 27.

Casual Fall Outfit Ideas With Jeans

The High Rise Button Fly in a Dark Wash

Jeans in a gray/black wash are one of my go-to pairs for Fall. I love pairing this color of jean with darker colored shoes – everything from booties to loafers. Wearing: Everlane Authentic Stretch High Rise Jean with Button Fly in size 28. Top with your favorite cropped cardigan or a long cardigan. I love wearing my favorite knitted sweaters with all my jeans!

Casual Fall Outfit Ideas With Jeans

The Stretchy Button Fly Jeans

The throw on and go jeans that look put together yet casual and have some room to breathe. The distressed hem makes these casual and perfect for the weekends and ensures they look great with ankle boots. Wearing: The J.Crew 9″ Toothpick Jean in size 27.

Everlane Boots and Blazers I wit & whimsy

The High Rise Stretch Skinny Jean

For the jean that will hug all your curves, provide some lift and not be too tight – look no further than these that’ll be perfectly dressed up or dressed down. Wearing: Everlane Authentic Stretch High Rise Skinny Jean in size 28.

Madewell Colorblock Cardigan I wit & whimsy

The Best Ankle Crop Jeans Ever

Wear them with essentially any type of shoe! These are super flattering on and hold up well to lots of wear. These are hands down my favorite jeans. Wearing: Agolde Toni Ankle Jeans in size 27.

The Chic Tweed Jacket I wit & whimsy

Black Jeans

Black jeans season is officially back when Fall rolls around! I prefer black jeans in an ankle crop length to pair with ankle boots or ballet flats. If you’re a fan of animal print, you could pair a printed animal print top with black jeans.

Here are more ways I’ve worn this style in the Fall for even more inspo around this style:

Casual Fall Outfit Ideas With Jeans

Barbour Icons Collection I 125th Anniversary I wit & whimsy

Ann Taylor Casual Blazer I wit & whimsy

Sezane Gaspard Sweater I wit & whimsy

French Girl Style Striped Tee I wit & whimsy

Cozy, Ribbed Cashmere Sweater I wit & whimsy

Casual Fall Outfit Ideas With Jeans

Casual Fall Outfit Ideas With Jeans

The Casual Dark Wash Jean

Bring some variety to your jeans outfits with a darker wash jean with some distressing. This pair is the Agolde Toni I love so much but in a cool new distressed hem version that I love juxtaposing with a more feminine flat but would also wear with a sneaker or bootie thanks to the ankle crop. Wearing: Agolde Toni Mid-Rise Distressed Jeans in size 27.

Inez Boot Review I wit & whimsy

Stretchy Ankle Crop Jeans

Get yourself a pair of soft, stretchy jeans for casual, comfy days! These “Rocket Crop” jeans go with just about every shoe in my closet. Wearing: Citizens of Humanity Rocket Crop Jeans in size 28. (Size down if you want a tighter fit.) 

Casual Fall Outfit Ideas With Jeans

The Chic Mom Jean

The Levi’s Wedgie Crop Straight Jeans are my mom jeans dreams come true. So flattering and great with a slingback or your favorite pair of pumps, these jeans are super comfy and soft. Wearing Levi’s Wedgie Crop Straight Jeans in size 28. Also available in a lighter wash here. Frayed hem version here.

Or try a similar style:

Everlane Drape Trench I wit & whimsy

The Cheeky Jean lifts your bootie and slims your hips! Wear them with your favorite tee and a pump or slingback. Wearing: Everlane Cheeky Straight Jean in 28.

Casual Fall Outfit I wit & whimsy

The Classic Blue Jean

This do-it-all jean will never go out of style. With a high waist you’ll get a flattering fit and it’ll be able to be styled with a myriad of shoe types. Wearing: Current / Elliot High Rise Stiletto Crop Jeans in size 27.

Ann Taylor Spring Try On I wit & whimsy

The Weekend Jean

With a lived-in wash and ever so subtle distressing, these jeans are made for more casual looks. Wearing: Agolde Nico Distressed Jeans in size 27.

Cute Cardigans for Fall I wit & whimsy

The Kick Flare Jean

A more trendy jean but one I love to pair with sock booties in Fall. These have a great distressed hem and are super soft to wear. I love pairing a kick flare jean with an oversized sweater or a cardigan. Wearing: Velvet Twiggy Jean in size 28.

Sarah Flint Natalie Bow Flat in Nude I wit & whimsy

The Classic Black Skinny Jean

No wardrobe is complete without a classic black skinny jean in my opinion. So versatile and I wear mine all Fall & Winter. I love to pair them with my collection of ivory sweaters, a great coat and a favorite shoe. Wearing: Agolde Sophie Ankle Crop Jeans in size 28.

Easy Fall Outfit I wit & whimsy

The Casual Black Mom Jean

A casually – cool mom jean with a high waist and more room throughout the legs. A cropped ankle length makes this pair great with mules, loafers, sneakers or flats. Wearing: Levi’s Wedgie Straight Jeans in size 28. I also have this pair in blue

Even More Cute Casual Fall Outfit Ideas with Jeans

Agolde Riley Jeans

AGolde Riley Cropped Straight Jeans – size 27

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Fall Neutrals I wit & whimsy

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Classic Camel Coat I wit & whimsy

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J.Crew Ruffleneck Sweater I wit & whimsy

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Sherpa Jacket I wit & whimsy

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J.Crew Ella Sweater Blazer

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How to Wear a Blazer Casually

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You can see even more of my favorite jeans here, see all my favorite Agolde jeans here (my favorite denim brand), read a full review of Evelane’s denim here and get the scoop on all my favorite pairs of shoes here.


And when you’ve had your fill of jeans, there’s always a return to leather legging season, too! 


J.Crew Sweater Blazer (S) // J.Crew Jeans (27) // Margaux Bow Flats (c/o; size up half size to 37.5) // MM.LaFleur Tee (M) // J.Crew Camera Bag


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12 comments on “Casual Fall Outfit Ideas With Jeans”

  1. Loved all of these! Thank you for all your hard work putting this together! I’ll be referencing this post for my fall outfits 🙂

  2. Hi! I love jeans too! You look great in all your outfits! I see you’re a fan of Agolde. I’ll have to try them on in-store. The dark pair looks great on you. I have a question. I have tried Everlane once. I bought a washed black pair with the zipper. The pair I bought bagged out really bad after just hours of wear. I see you have the button fly. Do they bag out at all? Thank you for this post. ??

  3. Out of all the things I missed during the pandemic, wearing real clothes is definitely high on the list. It’s been so nice to have occasions to get dressed more often.

    I love your style btw; it’s the perfect mix of classic and casual.

  4. This is awesome, thank you! I feel like every fall there’s a new denim cut and shoe in style…would love your take on the 2-3 must have shoes for the fall/winter and which denim cut to pair them with!

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