denim shirt and snakeskin skirt outfit

10 Classic and Trendy Dinner Outfits for Fall

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Cooler weather is coming, but it doesn’t mean you have to fall into the same routine of reaching for your typical go-to pair of skinny jeans and your favorite cozy sweater when you’re getting ready! Whether you’re looking for fall dinner outfits for a date night, or maybe cute fall outfits for a night out with the girls, autumn fashion provides plenty of choices when it comes to putting together the perfect fall outfit with both trendy and classic elements. With both timeless and current styles in mind, I’ve put together 10 classic and trendy fall dinner outfits perfect for an evening out this season!

1. Moody Reds for Fall: sweater tank + leather pants + heels

sweater tank and leather pants for a fall dinner outfit

pants | sweater tank | shoes | bag | lipstick

Leather pants are a great way to incorporate texture into your fall dinner outfits. Choosing to go with a pair in black or brown keeps them neutral enough that they don’t overpower the other pieces that you’re wearing, and pairing them with more feminine pieces like a classic pump heel will bring balance to your look.

Leather pants are naturally more of an edgy and trendy choice, and will shine with deep color tones like a dark red or maroon – like the shade of these classic pumps. The addition of a sleeveless turtleneck tank is a great choice when the weather is still transitioning, to help you from overheating. Choosing a softer fabric like a knit will offset a more structured one like leather.

Bringing the leather back in with your bag, but with a different texture like this woven one, keeps the material from becoming too repetitive. Finish the look off with a statement red lip to pull the outfit together, and for a little bit of drama that’s the perfect fall color!

2. Forever Chic in Red, White, and Black: satin skirt + cardigan + kitten heels

slip skirt and cardigan for a fall dinner outfit

cardigan | skirt | shoes | earrings | lipstick

White, black, and red will forever be a classic color combo and a personal favorite. Add your own flair to the tried and true combination by experimenting with different textures and materials.

A silk slip skirt provides some softness to the contrasting combination of colors. These come in all different lengths, no matter your style – whether you prefer something on the shorter side or a longer one like this that hits around the ankle. Silk always adds an element of elegance to your outfit, which is perfect if you’re dining somewhere where you want to dress up a little bit more than usual.

Next, adding a chunky sweater in a knit provides another texture to your look. It’s perfect for a cool night and fall weather, plus, these types of sweaters are almost always comfortable! The bows on this cardigan add a unique element, but you can also play around with different patterns or cuts – whatever suits your personal style.

A pair of statement earrings further elevates the first date look. To add a trendy twist to your look. look for a pair of earrings that incorporate both diamonds and pearls, along with gold. Finish it off with a pair of kitten heels for a timeless look – and a little bit of comfort!

3. A New Way to Wear a Leather Jacket: leather blazer + tank + jeans + animal print boots

leather blazer, tank top, jeans, and ankle boots for a for a fall dinner outfit

blazer | jeans | tank | boots | hat

This look would be perfect for a more casual date night or dinner with the girls! The leather blazer is a trendy piece, but if you find it in a more neutral color like black, it could easily be worn as a staple from year to year. It’s a variation of the black leather jacket, but slightly more formal, elevating this basic.

You’ll find them right now in so many various fits, whether it’s more tailored, oversized, long, or cropped, so there are plenty of options to choose from depending on your personal taste. Plus, it can be layered with all types of looks!

The animal print ankle boots with kitten heels add interest with a pattern that’s still relatively neutral, which blends well with the warm tones of the orange top. The tighter fit of the top, along with the high waist of the jeans, add length to your legs and look flattering even under an oversized piece like this blazer.

Want to top off the look with an accessory? If it suits your style, add a wide-brimmed hat like this one to your fall dinner outfits for a look that’s both fun and oozing spooky season vibes.

4. Mini Skirts for a Big Statement: sweater + blazer + leather skirt + flats

brown blazer, striped sweater, and leather mini skirt for a fall dinner outfit

sweater | blazer | skirt | flats

Who says a mini skirt can’t look elegant and classic? The perfect first date outfit or getting coffee after dinner, this look is an example of how the right styling can make a leather mini skirt look stylish and ideal for colder weather. First, add a warmer piece like a striped sweater to balance out the shorter length of the skirt. Stripes will always be a classic choice, especially in neutral colors.

Adding a long blazer not only adds warmth to your look but sophistication as well. The gold buttons only elevate the piece, making it look even dressier. Choosing a tone like this orange will not only remind you of autumn leaves but will also add warmth to the otherwise neutral-toned look.

For a further look of sophistication, Mary Jane flats give an autumnal, literary feel to your fall dinner outfits. Just add ankle socks or a pair of tights for the final touch!

5. A Long Skirt is Trending: leather skirt + cardigan + knee-high boots + belt

cardigan, leather skirt, leather boots for a fall dinner outfit

skirt | cardigan | boots | belt | earrings

Speaking of leather skirts, have you ever thought about trying a leather midi or maxi skirt? Even if you shudder at the thought of going back to your long skirt days, here’s how to style it in a cool and classic way perfect for a fall date outfit! This particular one has a more unique a-line silhouette, which adds a feminine flair to the traditionally edgier fabric.

An oversized cardigan helps to add a softer feel to the leather of the skirt. For a better way to add shape to the oversized sweater, add a belt at your natural waist for a flattering look.

And if you’re looking for a new way to wear the classic knee-high boot, choose a pair with a little bit of a heel, and a square or pointed toe for a more updated look. Add a pair of gold hoops to complete the look!

6. Autumn Academia: sweater + mini skirt + knee-high boots

classy and preppy fall dinner outfit

shirt | skirt | boots

This look is a studious take on classic fall attire. And by the way, not every outfit has to have fall colors like olive green or burgundy to be a fall outfit! The black, white, and gray color combo never goes wrong, and can still read “spooky” for the season. Head straight from a fun date at a haunted house to the restaurant in this great look.

As far as what’s trendy, the academia trend is everywhere right now, and this look fits right in! A collared sweater is the perfect top for this vibe, especially in a moody black and white. Add in the plaid skirt, and you will feel right at home in an old library or maybe on a university campus in the fall.

A pair of knee-high boots with a heel and a square or pointed toe is another trending way to update the staple for your fall dinner outfits. Finish the look with a pair of tights in slimming black. Play around with varieties of opaqueness if you want to try out different levels of sheerness. The more opaque, the darker the color, and the less opaque, the more sheerness.

When buying tights, you’ll see opaqueness measured in “denier,” which in fabric terms is a measure of fiber thickness. Opaque in hosiery is typically classified as anything 40 denier or higher, while below that will be more sure. If you’re worried about runs or rips, the higher the denier, the stronger the tight. But it’s all about what look you’re going for when it comes to which denier is best!

7. Denim Jacket Swap: denim shirt + shorts + knee-high boots

denim shirt, brown boots, leopard print belt, and shorts for a fall dinner outfit

shirt | shorts | boots | belt

If you’re looking for an alternative to the classic denim jacket for a fall date look, a button-up is a versatile take on the staple fabric that will give you lots of options for wardrobe pairings. It can be buttoned or added on top of another layer, even if warm weather is still hanging on. It pairs well with shorts, too.

For a sophisticated take, try a pair of trouser-style shorts like these to elevate the look. The loose fit and high waist are both comfortable and flattering. If you want to add another complementary element to the look, add a thin belt. You could choose a solid color, or add some visual interest by choosing a patterned belt like this leopard one.

Knee-high boots can be a better way to lengthen your legs than booties, and they help you keep warm in the cooler autumn months!

8. A New Take on Jeans and a Sweater: turtleneck sweater + jeans + mules

turtleneck sweater, jeans, and mules for a fall dinner outfit

sweater | jeans | shoes | bracelet

If jeans and a sweater are part of your go-to fall look, here is an elevated take on the classic pairing. A sleeveless turtleneck not only helps keep you cool if the weather is still warm, but also makes it easier to add another layer. Because it doesn’t have sleeves, you don’t have to worry about how bulky you’ll feel or how tight your arms might be if you add a jacket, blazer, or sweater over it.

Swap your skinny jeans for a boot-cut, flared, or ankle-length denim to update the look further with today’s trends. These styles all look great paired with ankle boots, or a shoe like a heeled mule. Instead of skinny jeans breaking up the length of your leg where the top of your shoe hits, a longer and looser look in your jeans will continue the line of your leg through the point of your shoe.

And if you pack a pair of flat shoes, this would be a great look to take you from apple picking to a nice dinner! Lastly, add a simple but elevated piece of jewelry, like diamonds, to help take the look to another level.

For more tips on what jeans to pair with what shoes: Your Guide on How To Wear Ankle Boots (and More) With Jeans, Plus Tips for Always Getting It Right

9. Black and White Elegance: cardigan + t-shirt + leather skirt + flats

chic, classy, and preppy fall dinner outfit

cardigan | shirt | skirt | flats

Black and white are timeless in this elegant look for fall. Playing with long and short lengths is a great way to add interest to your outfit, such as with a short skirt and a long cardigan. A long sleeve turtleneck makes it extra cozy.

The vertical lines of the black details on this cardigan add a slimming element to your look. Plus, gold buttons add a sophisticated detail for a fall dinner outfit. The leather adds that bit of edge, which you can accentuate with a bold red lip. A red lip is an accessory in and of itself! Plus, investing in quality lipstick, like the classic Chanel one, will make sure that your lipstick makes it through a night of dining, chatting, and laughing. It’s a small luxe detail that will have your whole look feeling elevated.

Add a statement shoe, like this pair of flats with a fun bow, to make your outfit all the more memorable. Choose a pointed toe rather than a rounded one for a more modern version of the classic flat.

10. Vests for Fall: vest + dress pants + boots

vest, dress pants, and ankle boots for a fall dinner outfit

vest | pants | boots | bag

Getting dinner with your coworkers? Grabbing drinks at a work conference? This work chic look is perfect for you. Even better, is that you can bring your vest with you from summer into fall with this look! A pair of wide-legged trousers will forever be a classic staple, and they add a further element of sophistication to the vest when it’s worn as a top. Plus, you may need the warmth of a longer pant when paired with the vest as autumn nights get cool.

Trousers pair well with a vest, especially since this style of pant is easily found in high-waisted styles if your vest is slightly cropped. If you’d like to add another layer, try a trench coat or a cozy sweater.

Add a pair of ankle boots for additional height if you’d like. For an updated version of the classic shoe, a slim heel and a pointed toe with a slightly higher ankle height are what’s trending in 2023. A structured black tote completes the look!

Choosing Your Look

Choosing stylish fall dinner outfits doesn’t have to be complicated! There are plenty of ways to add trendier elements to your outfit without losing your classic aesthetic or being a victim of the trends.

Layering (thanks to the cooler temps in colder months) offers a chance to mix staple pieces like a trench coat, chunky sweater, or little black dress with trendier ones. I also love layering for creativity! You can mix textures, fabrics, and patterns to create more unique and dimensional looks in the fall season.

Plus, it can be fun to mix both trendy and classic pieces for a fun night out, whether it’s for a date night or a night out with friends or family. And how about that amazing feeling of maximizing your wardrobe? Don’t be afraid to bring in traditional “summer” pieces to adapt them for fall. Shorts and sleeveless tops don’t have to be banished from your wardrobe until spring!

If you’re looking for even more fall outfit ideas, read this post for 46 super stylish fall date night outfits. Next Up: 46 Super Stylish Date Night Outfits to Wear This Fall


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.