Casual Fall Outfit Ideas With Jeans

November 3, 2020

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. (And btw don’t forget that the Sephora sale opens up to VIB today! Shop my picks here).

Sophie Blazer I wit & whimsy

J.Crew Camera Bag

Casual Fall Outfit Ideas with Jeans

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. 

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 reliable casual outfit ideas on how to wear your jeans this Fall and beyond.

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.

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.

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.

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. 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.

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.) I also own the distressed version

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.

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.

A New Favorite Casual Look for this Fall

The Weekend Jean

With a lived-in wash and ever so subtle distressing, these jeans are made for more casual looks and Wearing: J.Crew Toothpick Jean in size 27.

Or try this similar pair of casual jeans:

Ann Taylor Spring Try On I wit & whimsy

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

Or try a similar style in a kick-crop:

Everlane Kick Flare Jeans I wit & whimsy

Wearing: Everlane Kick Crop Jean in size 28. (I cut off about 4 in of the hem). 

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! This pair is my favorite (I own size M).


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

p.s. my big Fall & Winter shoe guide and my favorite workout clothes.

what I'm wearing

6 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. ??

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