Casual Fall Outfit Ideas With Jeans

September 13, 2023

Madewell Plaid Blazer Fall Outfit

While I am certainly loving the return of trousers and skirts for Fall – I will always be reaching for jeans again and again. I’m a jeans girl through and through and I love having a variety of styles in my wardrobe to put together casual outfits especially in the Fall season.

If you’re looking for ways to put together outfits for the forthcoming months using the jeans you have or are looking for some new styles to shop – this post is for you! Lots of cute outfit ideas coming your way for the fall season.

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 Jean

White jeans are not just for summer fashion in my opinion! I personally love to wear my white jeans well into Fall – most often in a monochromatic fashion. They pair perfectly with my collection of ivory sweaters.

This year I am loving more off-white denim. I recently picked up this pair in a pretty ecru and they are so good! I took my usual size 28.

With ecru or white jeans you also have the option of adding a classic denim jacket as a light layer.

Agolde Riley Jeans and Bash Paris Jacket Fall Style

The Dark Wash Straight Jean

Straight jeans are everywhere this season and I really like them in a dark wash pair to change things up. This is the Agolde Riley jeans in size 28.

I also love pairing this pair of jeans with a black blazer and a pair of Converse sneakers:

Paris Winter Outfit

Sezane Sweater I on Meghan Donovan of wit & whimsy

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.

Want to update your look for the season with an on trend style? Try a slouchier boot like these.

J.Crew Sweater Blazer Styling Ideas I wit & whimsy

Distressed Vintage Straight Jeans

These jeans feel lived in right away. They have a vintage vibe to them and some distressing perfect for casual or weekend wear outfits. I really like Madewell’s distressed styles.

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.

Even if skinny jeans are less popular now, I still think they make sense with certain casual Fall outfits. And as you always should…wear what you want and what you like!

Sezane Navy Blazer, Agolde Riley Jeans, Alex Mill Striped Tee and Margaux Mules

The Straight Leg Ankle Crop

High rise, fitted and cropped at the ankle with a straight let – the Agolde Riley jeans fit the bill for so many jeans looks in the Fall. I have them in a true blue wash and a dark wash, too. See the rest of the above outfit here: Navy Blazer and Striped Tee.

Check sizing on the various styles of this jean. Some have stretch, some don’t! I wear a size 28 in some styles and a size 27 in other depending on the jean fabric. 

Ann Taylor Spring Try On I wit & whimsy

Another straight leg style I love is the Levi’s Wedgie Jeans. They hit me right above the ankle and I love them with flats or mules. I’m wearing a size 28.

I also own and love the Wedgie Icon Jeans and the 501 Crop Jeans. All size 28. Levi’s jeans are just so, so good and so well priced.

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. I love pairing my gray jeans with blazers and ivory knits this time of year.

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. 

Or try a similar style:

Everlane Drape Trench I wit & whimsy

The Cheeky Jean

The Cheeky Jean lifts your bootie and slims your hips! Wear them with your favorite tee and a pump or slingback. Great if you have a curvier frame. 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.  I like the Madewell 10inch High Rise Jeans.

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.

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. Shop a variety of styles here.

This year I am more into gray washes but I’ll keep my classic black jeans for whenever I want to pull them out. 

Easy Fall Outfit I wit & whimsy

The Casual Black Straight 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

The Straight Leg Jean

Hitting longer and below the ankle, this is a on trend style for this fall. 

Fall Outfit featuring Veronica Beard Blazer, Agolde Straight Leg Jeans, Manolo Blahnik Ballerina Flats

Jeans with a Ball Cap and Blazer

I love the preppy meets tomboy vibes when you combine wearing a plaid blazer with a ball cap and adding a more feminine shoe like a ballet flat.

Wearing above the Agolde Riley in MidRise – size 28.

Paris Outfit with Celine Bag Chanel Shoes and Trench Coat by Sezane

Jeans with a Trench Coat

For Fall’s rainy days, pair your favorite shoes with a great trench coat. If you need more styling ideas, don’t miss my Cute Trench Coats for Fall post.

J.Crew Lady Jacket Stripes Spring Outfit

With a Lady Jacket

Pairing a lady jacket or knit cardigan buttoned up with a good pair of cropped, high waisted jeans is an easy outfit formula I follow regularly.

Gucci Loafer

With Loafers and a Plaid Blazer

This is one of my most worn outfits every Fall! You can shop my collection of blazers HERE.

Freda Salvador Boot Fall Outfit

With Lug Sole Boots and a Quilted Jacket

Perfect for casual Fall adventures spent making memories outdoors, I love to add a practical, waterproof lug sole Chelsea boot with an oversized quilted jacket and a favorite cashmere sweater

With a Kitten Heel Mule

This timeless shoe style always looks so elegant and I love to pair it with jeans with a slightly distressed hem that hits at the ankle.

Fall Outfit with & Other Stories CoatF

With an Oversized Wrap Coat

As Fall temperatures take a dip, add. a stylish oversized coat atop your favorite casual Fall outfits. Seen wearing this one above in a size Small.

Cashmere Turtleneck I wit & whimsy

With a Turtleneck

With the return of jeans weather in the Fall comes the return of turleneck weather. Add a turtleneck sweater in a pretty neutral with a gray pair of denim for autumnal vibes. I also really like pairing black and brown this time of year as an alternative. It’s such a chic and timeless color combination.

DL1961 Enora Cigarette High Rise Jeans

With Kitten Mules

If you’re like me and often avoid the element of a pop of color, try a tonal look with a wide leg jean and kitten mules.

Even More Cute Casual Fall Outfit Ideas with Jeans

J.Crew Lady Jacket Fall Outfit

Everlane Half Zip and Jenni Kayne Shearling Mules

Related: Jenni Kayne Mules Review

Paris Fall Outfit LaLigne sweater

Paris Blazer Outfit

Black Converse in Paris Outfit

Fall Outfit in Paris with a Trench Coat

Ankle Crop jeans with a Trench Coat and Mules

Agolde Riley Jeans

AGolde Riley Cropped Straight Jeans – size 27

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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! 


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comments +

  1. Hannah says:

    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. Melissa says:

    This is a great post! Lots of good ideas! Thanks!

  4. Lauren says:

    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.

  5. Whitley says:

    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!

  6. Katie says:

    You have such great jean style! I’m more inspired to make monochromatic looks this fall.

  7. Maiju says:

    Hi Meghan, I just wanted to tell you how I love your style! Your blog and Instagram account is the place to go for me when I need inspiration, cheering up… Have a great week!

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