classy fall outfits

15 Classy Fall Outfits for Every Occasion

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And just like that, the calendar has flipped to a new month. And though it may not feel like fall yet weather-wise, it’ll be here before you know it, and that means it’s time to start thinking about classy fall outfits! Whether you’re heading to the office, a work conference, a parent-teacher conference, a fall wedding, Thanksgiving, or another special event, it’s a good idea to have some chic and classy looks tucked away for when you need them. Save and recreate these 15 stylish and classy fall outfits that are perfect for any occasion!

1. sweater vest + slip skirt + ballet flats

classy fall outfits

vest | skirt | shoes | necklace | purse

This outfit combination is perfect for the early fall season or for those that live in warmer climates. It’s a great way to transition from the summer to the cooler months without sacrificing fall style.

A sweater vest is a classic piece that adds a touch of sophistication to any outfit. Paired with a slip skirt, it creates a feminine and chic look that is effortlessly stylish. The silk-inspired material adds a touch of elegance, while the sweater vest keeps it cozy and comfortable. Plus, the sleeveless detail of the sweater vest keeps you from overheating!

To complete the outfit, opt for a pair of ballet flats or Mary Jane flats. These shoes are not only comfortable, but they dress down the skirt while still adding a touch of polish to the look.

2. turtleneck + blazer + mini skirt + loafers

classy fall outfits

turtleneck | skirt | socks | shoes | blazer | earrings

For a preppy meets classy style, this combo is a go-to outfit for the fall season! The cooler weather is the perfect time to embrace outerwear, and blazers are one of the best ways to create some classy outfits. This combination exudes preppy sophistication while keeping you cozy and comfortable.

Start off with a turtleneck, a staple piece that never goes out of style. Choose a classic color or classic print to create a timeless look. Pair it with a blazer in a complementary color to add structure and polish to your outfit. The blazer instantly elevates the overall look, making it one of the best items to have in your fall wardrobe.

Next, choose a skirt with a flattering length for you (whether that’s a mini or not) and pair it with loafers and socks for a chic and effortless vibe. The loafers provide both style and comfort, making it easy to navigate through your day while looking put together.

3. lady jacket + slip skirt + ankle boots

classy fall outfits

lady jacket | skirt | boots | earrings | bracelet

When it comes to a classy fall outfit, you can’t go wrong with this one. The pairing of the slip skirt with a lady jacket creates a fabulous outfit that exudes sophistication and elegance! The lady jacket already adds a touch of class and refinement to the outfit, but choose a tailored jacket in a neutral color like black or camel for a timeless look.

Pair it with a slip skirt, which adds a touch of femininity and elegance. A slip skirt in a luxe fabric like silk or satin (or similar) adds an extra glamorous touch. Not to mention the slip skirt’s sleek and chic silhouette is always effortlessly stylish.

Complete the outfit with ankle boots to add a timeless yet current edge to your outfit. Get ready to feel like a fashion icon in this chic and classy outfit!

4. plaid blazer + denim skirt + loafers

classy fall outfits

blazer | shoes | skirt | bag | bracelet

If you’re looking for a classy fall outfit that’s both chic and timeless, look no further than this outfit idea. This outfit is perfect for those days when you want to embrace fall and the back-to-school feeling. The plaid blazer is a must-have for the fall season, but other classic plaid patterns like houndstooth or checkered are great too.

Pair the blazer with a denim skirt, a versatile piece that can be dressed up or down. If you like longer skirts, don’t be afraid to go with a midi length, and style it with confidence! Denim skirts are perfect for achieving that effortless cool-girl vibe while still looking put together.

Complete the outfit with a pair of loafers – one of the best shoe choices to add a touch of sophistication to your look.

5. sleeveless turtleneck sweater + dress pants + mary jane heels + poncho wrap

classy fall outfits

sweater | pants | shoes | poncho | brooch

It doesn’t get much classier than this. Start off with a sleeveless turtleneck sweater, which adds a touch of elegance to your outfit while also being a good choice for warmer climates. Choose a neutral color like black or beige for a timeless look.

Pair it with dress pants in a matching color to create a polished and put-together monochromatic outfit. Flowy dress pants are not only stylish, but they can also be really comfortable, making them perfect for a day at the office or a special event.

Shoe-wise, opt for a pair of Mary Jane heels. These shoes are classic and feminine, adding a touch of sophistication to any outfit. Choose a pair in a neutral color like black, brown, or nude to keep the focus on the overall look.

To complete the ensemble, drape a poncho wrap over your shoulders and secure it with a brooch. Poncho wraps are not only beautiful but also functional, providing an extra layer of warmth on cooler days when you need it. This ensemble is also perfect for those transitional days when the weather is still a bit unpredictable.

Related: 7 Chic Ways to Wear a Brooch

6. cable-knit cardigan sweater + midi skirt + ballet flats

classy fall outfits

cardigan | skirt | shoes | bag | earrings

For a look that strikes the right balance between cozy and elegant, this is it. The cable-knit cardigan sweater is not only cozy and warm, but it also adds a touch of texture to your outfit, playing well with the pleated, chiffon-inspired skirt.

Midi skirts are a great idea because they are perfect for creating a feminine and elegant silhouette, while still providing comfort and mobility.

Complete the outfit with a pair of ballet flats, and to add an unexpected stylish element, opt for an animal print. Whether you’re going to church, brunch, or Thanksgiving, this outfit is sure to make you look effortlessly chic and put together!

7. slip dress + cardigan + block heels

classy fall outfits

dress | cardigan | shoes | earrings | bracelet

Need a look for a date night or dinner party? Try this one on for size. Slip dresses are an elegant and versatile piece that can be styled with different outerwear and accessories to easily switch up the look. Choose a slip dress in a classic color like black or navy to create a sleek and elegant look, or opt for one in a fall color to give a nod to autumn.

Pair the slip dress with a cozy cardigan to add warmth and coverage to the outfit. Complete the outfit with a pair of block heels. A small block heel is the perfect compromise between style and comfort. These shoes provide extra height and lengthen your silhouette, but they also offer stability and comfort for all-day wear. You could also swap them out for strappy heels, depending on your climate.

8. striped jacket + jeans + animal print shoes

classy fall outfits

jacket | jeans | shoes | bag | earrings

If classy fall outfits to you mean dressing up a pair of jeans, then this is the look for you. This outfit combo is a perfect fall outfit for those days when you want to make a bold statement with your fashion choices, while still looking appropriate for your day-to-day.

Start off with a striped jacket, a piece that adds a pop of color and pattern to your look. Choose a jacket with an extra detail, such as gold buttons, to elevate the piece even more.

Now onto the jeans. Whether you choose blue jeans or black jeans, consider giving your skinny jeans a break and swapping them out for a boot crop style to highlight a statement shoe. When it comes to statement shoes, choose a pair of animal print shoes to add some personality and flair to the ensemble. Whether you choose leopard, snake, or zebra print, pick something that suits your personality and makes a statement!

9. sweater + cardigan + denim skirt + knee-high boots

classy fall outfits

cardigan sweater set | skirt | boots | earrings | tights | belt

When it comes to cute fall outfits, this ensemble is perfect for those crisp autumn days when you want to look stylish while staying warm.

Start off with a classic cable knit sweater, and bonus points for a matching set. But don’t worry, you can always create the look by layering a cardigan over a coordinating sweater! Either way, this creates a warm, fashionable, and layered look.

Next, pair the sweater and cardigan with a denim skirt. To showcase your knee-high boots, choose a denim skirt on the shorter side. Whether you’re heading to a coffee date, pumpkin patch, a day of shopping, or a casual outing with friends, this outfit will make you feel put together and stylish.

10. cable knit sweater + shorts + socks + loafers

classy fall outfits

cable knit sweater | shorts | socks | shoes

Preppy meets classy in this back-to-school-inspired look. This ensemble is all about mixing unexpected pieces to create a fashionable and comfortable look.

Start off with a cable knit sweater, a fall staple that adds texture and warmth to your outfit. Pair it with a pair of shorts in a complementary color. Shorts may seem unconventional for fall, but they can add a fun and unexpected element to your outfit.

To keep your legs warm and to add a trendy touch, layer on a pair of cozy socks. This small detail will not only keep you comfortable but also elevate your overall look. Lastly, complete the outfit with a pair of loafers. These are prefect for completing your preppy look and adding a touch of sophistication and polish to your outfit.

11. trench coat + striped turtleneck + jeans + loafers

classy fall outfits

trench coat | turtleneck | shoes | jeans | earrings

A long coat is one of my favorite ways to add some class. Even better is when you pair long coats with cozy sweaters! This combination is a classic and stylish fall outfit that never goes out of style and is especially perfect for those cooler days when you want to look effortlessly chic and put together with minimal effort.

Start off with the classic trench coat, a timeless piece that adds a touch of Parisian sophistication to any outfit. Pair it with a striped turtleneck for a pop of pattern and visual interest. Stripes are always in style!

Next, opt for a pair of jeans in a flattering fit and wash. Jeans are a staple in any wardrobe and provide a casual yet polished base for your outfit. Whether you choose skinny, straight, or boyfriend jeans, just make sure they are comfortable and make you feel confident. Loafers complete the look with a touch of sophistication and polish.

12. tweed jacket + dress pants + flats

classy fall outfits

jacket | pants | shoes | bag | earrings

Lady jackets are having a moment, but no matter what the latest trends are, they are perfect for the autumn season. Not too thick but not too thin, this wardrobe piece can be dressed up for chic fall date night outfits or dressed down with denim jeans and white sneakers for stylish casual wear.

For a formal or professional setting, you can’t go wrong with this polished and sophisticated fall look. The lady jacket adds a touch of refinement to your outfit while dress pants provide a tailored and polished silhouette, making them a staple in any sophisticated wardrobe.

To keep the outfit from looking too dressy (unless the occasion calls for it), slip on a pair of simple ballet flats.

Related: Fall Wardrobe Checklist: These Items Just Scream “Fall”

13. short sleeve jacket + tailored shorts + boots

classy fall outfits

jacket | shorts | boots | earrings

A short-sleeved jacket paired with shorts and taller boots is perfect for those in-between days when the weather is still transitioning. This combination is all about balancing style and comfort for a fashionable look that is effortlessly cool. (And still classy!)

Start off with a short-sleeved jacket in a neutral color for a timeless and classic look. Pair it with a pair of tailored shorts, which add a hint of playfulness and youthfulness to the outfit.

To complete the outfit, slip on a pair of boots. Tall black leather boots not only add a touch of edge and attitude to your look, but they also provide more leg coverage. This fashion-forward look is great for a casual day of shopping or meeting friends for a brunch date.

14. trench coat + jacket + shorts + boots

classy fall outfits

coat | jacket | shorts | boots

Classy meets Parisian chic in this look! Play with proportions by pairing your long trench coat with a cropped jacket, tailored shorts, and tall boots. The shorts balance out the longer lengths of the trench coat and shoes, while the tailored shorts keep the outfit looking classy. The contrast in lengths creates an end result that is youthful and playful – yet still sophisticated and chic!

With the double outerwear layers, this outfit idea is ideal for those in cooler climates who need extra layers to stay warm.

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15. button-up + vest + shorts + oxfords + socks

classy fall outfits

shorts | white button-up | vest | oxford loafers | socks

This outfit combination is a trendy and fashion-forward fall outfit that is perfect for those who want to make a bold style statement. This ensemble is all about mixing unexpected, masculine pieces to create a unique and edgy look.

Start off with a button-up shirt, a classic piece that adds structure and polish to your outfit. Layer on a vest for added style and texture. Next, pair the button-up and vest with a pair of tailored shorts.

To complete the outfit, slip on a pair of oxfords. Oxfords are perfect for creating a preppy, back-to-school-inspired outfit. Last but not least, finish off the look with a pair of socks to add an extra pop of style.

Though you may be swapping out the white tank for a sweater vest and the bright colors for earth tones, this new season provides so many opportunities to get creative and discover your new favorite fall outfits!

But creating fall outfits gets really difficult if you don’t have the wardrobe staples. Enter: fall capsule wardrobe. This is the perfect way to ensure you’ll have the perfect outfit for whatever comes up – whether you’re going to the grocery store or a special event. Up Next: Classic Fall Capsule Wardrobe (Shopping List, Outfit Ideas, & More!)


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.