16 Casual Fall Outfits To Wear Now & Later |

When it comes to style and outfits, fall is my favorite season. The inevitable layers make fall the best season to showcase your street style outfits. The layers, the textures and colors of fall make casual fall outfits instantly chic and cool. Not sure how to transition or what to wear in this new season? Don’t rush to put those summer maxi dresses and shorts away just yet. I’ve rounded up some of my favorite casual fall outfits that balance comfort and style, make you feel put together whether you’re heading to work, school pick up or on weekend errands.

Casual Fall Outfits

Before I dive into the outfit inspiration, let’s talk about the idea of a casual dress code. Casual attire is all about relaxed, comfortable clothing that still feels polished. Think casual wear like jeans, sweaters, button down shirts, and polo shirts, styled in a way that looks intentional. Unlike business casual, which leans more professional with dress shirts and slacks, casual outfits leave room for creativity, layering, and even incorporating elements of street style.

Understanding what casual means in the fall will help you decide how to dress for different outings without worrying about whether you’re underdressed. Let’s break it down further.

What Does Casual Dress Code Mean In The Fall

A fall casual dress code usually means clothes that are comfortable but thoughtfully styled. It’s not formal clothes or office ready attire, but it’s also not loungewear. (Though I still believe there is room for active wear in your casual wear closet.) Think of it as a middle ground between everyday casual attire and semi-dressy pieces. For women, casual fall outfits might include skinny jeans paired with chunky knit sweaters, denim skirt outfits, layered button down shirts, or even sweater dresses with boots.

The key is layering: fall temperatures can swing throughout the day, so a tee shirt under a cardigan, or a button down shirt with a sweater over the shoulder makes it easy to adjust your look as the weather changes.

What to Wear in Fall for Casual Events

Below are some casual fall outfit ideas that can inspire your wardrobe this season. Each one can easily be mixed and matched to create new looks, giving you endless options for casual events.

Outfit Idea 1 : Wide Leg Jeans, White Button Down + Classic Trench Coat

The ultimate casual fall look. A pair of wide leg jeans is a classic foundation that works for almost anything. Pair them with a crisp button down shirt, and finish with ballerina flats in suede for a trendy touch. Top this look with a classic trench coat for an effortless and chic look you can wear to the office, lunch and beyond.

Accessorize with a structured handbag, I love the burgundy hue for fall in this Madewell bucket bag. Add a pair of gold earrings and sunnies. This outfit is perfect for the office, matcha dates, or weekend brunch and errands.

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Outfit Idea 2: Silk Skirt, White Tee + Cropped Trench

One of my most favorite current trends is adding a silk or satin skirt to your casual wear closet. You no longer have to wait to dress it up. Instead wear it casually with a white tee and top with a cropped trench in similar hue as the skirt for a monochromic vibe.

I also love adding a fun leopard or animal print shoe and an everyday tote. A few stacked necklaces and a pair of sunglasses complete this easy fall look. I love this for the office, errands in the city or to volunteer at school, meet a friend for lunch and shopping or even as a comfortable teacher outfit idea.

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Outfit Idea 3: Chambray Shirt, Linen Pants & Fun Sneaker

For those transitional fall days, a good pair of linen pants from your summer closet pairs perfectly with a tank topped with a chambray shirt. A touch of denim paired with a fun and casual sneaker and an easy hands free bag is perfect for mom on the go, a day of sightseeing, early fall activities, the park, lunch and so much more.

Add a fun bracelet stack to elevate this casual early fall look.

For more ways to style a denim or chambray shirt check out this post: How to Style a Chambray Shirt

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Outfit Idea 4: Slacks and a Fitted Vest

This stylish fall look can go from formal clothes to casual with a few simple swaps. If you’re looking for business casual with a little street style edge this outfit fits the bill. Instead of a dress shirt we opt for a vest with a high neckline, which still makes it work appropriate. I love the idea of adding a flat shoe with some fun grommets for added details. The woven bag and tasteful jewelry make this an easy outfit to wear this season. On colder days consider layering a simple long sleeve top under the vest.

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Outfit Idea 5: Ecru Denim Jeans & Crochet Top

This monochromatic cream look is perfect for early fall, especially when paired with a crochet top and suede mary jane flats. The ecru jean style is perfect for this time of the year, and you can wear them long into the fall season. This outfit is perfect for a coffee date, the movies or early dinner with the family or fall get togethers with friends.

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Outfit Idea 6: Straight Leg Jeans & Knit Top

This classic date look is perfect for fall. You can even swap the straight leg jeans for a pair of your beloved skinny jeans. (If you still have those, I won’t tell.) I love that the moody vibes the burgundy details of the heels and the bag. I also love adding a silk scarf to this basic outfit idea to make it on trend.

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Outfit Idea 7: Denim Jacket & Slacks

Does a fall casual outfit idea even exist without a denim jacket? This one will always be a staple all year around for me. It’s so effortless and goes with anything and everything. I love pairing it with slacks for a bit more elevated casual style. A simple striped tee, a fun ballerina or mary jane flat shoe and a scarf make this basic casual outfit idea chic and modern.

For more outfit ideas with a denim jacket take a look at this post : Denim Jacket Outfit Ideas

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Outfit Idea 8: Blouse & Barrel Jeans

Love them or hate them, ( I love them) but barrel jeans are not going anywhere. You can pair these fun style denim with anything from polo shirts to a dress shirt. This blouse is an easy way to create a casual outfit that feels on trend while also being comfortable. This is perfect for everyday errands and even casual work days.

For more ideas how to style and wear barrel jeans take a look at this post : How to Style Barrel Jeans

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More Casual Fall Outfits To Wear

You’ll see repeat key pieces throughout this series of casual fall outfits, this is intentional. Building a perfect casual wardrobe means utilizing a capsule of your favorite pieces and pairing them in various ways.

Some of my favorite fall trends to incorporate this season:

Ballerina flat and mary janes, from animal print to mesh these really modernize your fall closet.
Silk scarves are also everywhere this season, I love adding them as an accessory to elevate a basic fall outfit.
On the other hand classics such as a good trench coat, or a cropped one. A really well made knit sweater and cardigan. A white tee and a classic button down are all great elements to update or invest, as they remain in style for years to come.
A great pair of jeans also makes a difference. Find one that you can wear on repeat. At the moment my favorite denim brand is Pistola. I find their fit universally flattering and the wash to be beautiful while being reasonably priced. [ Read my review of Pistola Denim ]

Outfit Idea 9: Denim on Denim

When I feel like I have nothing to wear I always gravitate towards the Canadian Tuxedo look. I love a good chambray shirt paired with jeans with a focus on fun accessories like these animal print mary janes. This outfit is great for weekend outings, dinner with friends or errands. It’s effortlessly chic when paired with the right accessories.

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Outfit Idea 10: Lady Jacket, Jeans & Ballerina Flats

This simple and stylish alternative to a cardigan is somewhere between a structured cardigan and a light jacket. A perfect fall option. A lady jacket paired with a popular denim, like this barrel style jeans and leather ballerina flats is the epitome of casual in. Wear it to the office, volunteer at school, lunch dates and anywhere else.

Pair with one of my favorite bum bag from Clare V for an elevated and contemporary touch.

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Outfit Idea 11: Cropped Trench Coat, Ecru Jeans & Suede Ballerina Flats

A cropped trench is a fun and useful addition to your fall closet. It pairs well with any outfit, and gives a structured intentional style. Pair it with light jeans and suede ballerina flats for a monochromatic look that’s perfect for fall activities. I love adding a belt to this simple outfit idea for added visual interest.

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Outfit Idea 12: Denim Skirt & Cropped Cardigan

A denim skirt outfit is such a versatile choice in the fall and it pairs perfectly with a cropped cardigan helping define the waist. It’s a great outfit for transitional weather and a denim skirt is a great closet staple.

Find more ways to style a midi denim skirt this season [ How to Style a Denim Skirt]

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Here are the best boots for fall.

More Fall Outfit Ideas For Transitional Weather

Outfit Idea 12: Striped Sweater & Leopard Print Pants

In my book animal print is a neutral, and these leopard print jeans pair perfectly with everything you already have in your closet. Add a simple black tank and layer with this amazing sweater from Quince for a comfortable on the go look.

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Outfit Idea 13: Cargo Pants & Short Sleeve Sweater

The comeback of the cargo pants wasn’t on my list for 2025, but honestly I got my pair last Spring and have worn them consistently over the last few months. A great and easy piece to transition into fall outfits, especially paired with a short sleeved sweater. I love the butter yellow and of course the addition of a little animal print for added texture and visual interest.

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Outfit Idea 14: Crochet Top, Trench & Straight Leg Jeans

Crochet is still a big trend going into fall months, so I say let’s use those tops and layer with cropped cardigan for perfectly trendy transitional outfits this fall. Add your favorite pair of jeans, and accessorize with green and brown fall colors and suede for added autumn vibes.

I love this look for date nights or weekends exploring a new city.

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Outfit Idea 15: Maxi Dress Layered with Denim Jacket & Woven Accessories

And don’t forget: the right accessories and beauty look can elevate your casual attire instantly. Pairing these outfits with a simple casual makeup routine makes everything feel put together without the fuss.

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Another way to prepare for the arrival of a new season is with a quick makeup routine update. Here is my post with favorite products for glowy, not overly done makeup for everyday.