20+ Chic Fall Date Night Outfits You’ll Feel Amazing In! (2024)

Looking for fall date outfits that are chic and stylish? You’ll love this list of 20+ chic and modern fall date night outfit ideas for 2024 that have an elevated, minimal, and classy vibe!

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My Fave Cute Fall Date Outfits for 2024

As summer transitions to fall and you begin changing out your closet, you might be looking for fall outfit inspiration, specifically fall date night outfits. I’m here to help! Read on to see my top chic fall date night outfits, as well as looks from my favorite fashion influencers!

The best way to dress for fall is in light layers, sweaters, jeans, sweater dresses, and boots or heels! These are all my favorite pieces to pair together for a chic fall date night outfit. I also choose mostly neutral colors like ivory, cream, black, and grey paired with rich, fall colors like rust, forest green, camel, and brown.

Scroll on for outfit inspiration!

rib-knit dress & leather jacket.

woman wearing a black midi dress with a black leather jacket around her shoulders and black ankle boots — @style.your.occasion

get the look:

When it comes to date nights, I believe you can never go wrong with a little black dress.

In this look, I opted for this super comfortable cashmere-cotton blend dress from Quince. The black dress is sleek and flattering and looks great with an oversized leather jacket layered on top.

For a cool date night, I opt for sleek ankle boots, but you could easily go with regular pumps or even heeled sandals if it’s early fall and the weather is still warm-ish.

chunky cardigan, denim mini, & boots.

woman wearing a denim skirt with talk black heeled boots and a brown cardigan. — @style.your.occasion

get the look:

This simple and flirty look is so easy to recreate and has a great fall vibe. Pair a cozy cardigan (this affordable cashmere cardi is my fave!) with a denim mini skirt and add a pair of tall boots. I love these tall black boots from Poppy Barley, but you can also go with a suede boot for a fall feel.

denim midi skirt, leather jacket & kitten heels.

woman wearing a denim midi skirt with a black tank top and a black leather jacket with black kitten heel sandals — @style.your.occasion

get the look:

This cool and classy look is one of my favorites for a fall date night when the temperatures are still warm. Above, I’m wearing my favorite distressed leather jacket with a scoop neck top and denim midi skirt from Aritzia.

A chic belt and kitten heel sandals add a dressy touch to the look and I’m ready for dinner and drinks!

chunky turtleneck and leather pants.

woman wearing a grey turtleneck with black leather pants and white heeled sandals — @style.your.occasion

get the look:

For a fall date, you can easily stick to the classics – leather pants and a chunky knit turtleneck sweater. Then, add a little pop of contrast to the look with white heeled sandals and an 0ff-white clutch.

This look is classy and comfortable, perfect for a cozy dinner date in autumn.

denim midi skirt, bodysuit & leather jacket.

get the look:

My long denim skirt is one of the newer additions to my wardrobe and I absolutely love how versatile it is. Because of its length, it’s the perfect choice for an early fall date night.

I paired it with a black bodysuit and kitten-heel sandals, although I’d switch out the sandals for heeled ankle boots if the night was going to be chilly. The black leather jacket is the perfect cherry on top, in my humble opinion! It’s sexy and adds an edgy element to the look.

To finish, I’ve gone with my favorite designer shoulder bag, but you could easily bring a simple clutch or a cute purse with a pop of color like red or a metallic finish.

knit midi dress, leather jacket + boots.

get the look:

If I want to feel cute but casual on a fall date night, I’d opt for a comfortable knit midi dress with a leather jacket and Chelsea boots. This look is dressy enough for date night but comfortable enough for lots of walking and hanging out in.

This look would be perfect for a comedy club date, visiting a new restaurant, or taking in a wine tasting at a winery.

striped knit, jeans + kitten heels.

get the look:

I love a pair of vintage-wash denim for a casual date night, like these B-Sides Jeans I’m wearing above. In my opinion, this outfit definitely screams comfy, cool, and effortless.

To get this look, pair jeans with a cozy striped knit sweater and low pumps or kitten heels. This fall date night outfit is perfect for dinner and a movie or drinks at a semi-casual spot.

oversized cardigan + leather leggings.

Woman wearing black leather leggings, a white tank top, a beige cardigan and black pumps. — @style.your.occasion

get the look:

Want to be as comfortable as possible but still look chic? I get it! Black leather leggings with an oversized cashmere cardigan is the perfect way to achieve this.

With this outfit, I always look and feel cute, and cozy, but still dressed up enough for a date night. Plus, if I get a little warm, I can always shed the cardigan and rock a knit ribbed cami underneath.

silk slip skirt + boots.

Woman wearing a black slip skirt, a white tank top, boots and a cream cardigan tied around her neck. — @sylviemus_

get the look:

Next is a look from the beautiful Sylvie, one of my favorite style icons.

In this outfit, a silk or satin slip skirt with a basic tank and lug boots make the perfect combo for a concert date or drinks on a rooftop. Throw a cozy sweater over your shoulders for a layer of warmth like Sylvie, and you can easily recreate this effortless look.

Pro tip: Be sure not to leave for your date with clumpy lashes – try these hacks for how to fix dry mascara!

leopard dress + black blazer.

woman wearing an oversized black blazer over a leopard slip dress — @mahdiness

get the look:

Leopard print is one of the top trends of fall 2024 and it is the perfect choice for a date night. Paired with an oversized black blazer and red or black pumps – perfection!

Not into animal print? A floral midi dress would look just as chic.

Dressing to the nines and putting in that extra effort to look beautiful for your beau is one of the many ways how to show someone you love them. And in a dress like this, you’re significant other will have no doubts in their mind!

Mini sweater dress + tall suede boots.

Woman wearing a cream colored, sleeveless sweater dress and tall, brown suede boots. — @jaimeshrayber

get the look:

This next fall date night outfit idea on Jamie is sexy, yet warm and cozy. I love the combo of the knit mini dress with the tall suede boots. The suede is perfect for fall and the sweater dress gives a cozy feel while still showing a little leg.

On a chillier evening, I would recommend the addition of a long, belted wool coat, to add warmth while keeping the vibe elevated and classy.

leather pants + dressy top.

Woman wearing black leather pants and a white silk top. — @lovefashionfriends

get the look:

Will you be grabbing dinner and drinks at a fancy cocktail lounge for your fall date night? Go with this stylish outfit on Dileiny of @lovefashionfriends.

The black leather pants are sexy, yet subtle, and paired with a flirty silk top and simple black pumps, the overall look is elevated and polished. One look at you in this outfit, and you’ll definitely be getting a second date invitation!

knit tunic + straight-leg jeans.

Woman wearing black jeans, brown booties, and a sleeveless knit sweater. — @lauren_bakewell

get the look:

A sleeveless sweater or tunic is the perfect transition piece for those warmer fall days and nights. I love how this sweater on Lauren is paired with vintage-wash black jeans and heeled booties for an effortlessly cool look.

This outfit is casual but still chic. You can dress it up or down depending on your date night activity. But if you’re planning on walking a lot, you may want to switch out the booties for a lower heel or sneakers.

denim midi skirt + suede.

woman wearing a suede jacket over a white tank with a denim midi skirt and suede boots — @_santinaharrison

get the look:

A denim midi skirt paired with a suede jacket is a seriously stunning combination!

I love the warm tones from the brown suede jacket and boots that instantly give this outfit on Santina a fall feel. And the midi skirt will add warmth while keeping a chic and feminine vibe.

I love the idea of a suede shirt jacket like this one to keep you cozy on a chilly fall evening, and the oversized fit has a relaxed vibe that I’m digging. With an outfit like this, you’re sure to look stylish and feel confident all night!

Cold Fall Date Night Outfits

When the weather is really chilly, you’ll want to add layers to your fall date night outfits. But you can still look cute doing it. See how below!

faux fur jacket, denim + boots.

Woman wearing jeans, black booties, a black sweater and a white faux fur jacket. — @juliaberolzheimer

get the look:

Leave it to Julia to create a gorgeous cold date night outfit with a cozy faux fur coat. I love how she paired the coat with straight-leg denim, a fitted turtleneck sweater, and heeled booties.

This look is great for a chilly night on the town, an outdoor concert, or a casual dinner. In my opinion, an outfit like this is also very versatile, effortless, and timeless because of the use of neutrals and staple wardrobe essentials.

leather pants + layers.

woman wearing a knit tank and cardigan set with leather pants and wine colored pumps for a fall date night outfit — @jordannasharp

get the look:

Gahhh, I just love this fall date night outfit by Jordanna Sharp.

In this outfit, she effortlessly layers a ribbed tank under a knit cardigan to stay warm and still look chic all evening. And the leather pants make the whole ensemble more dressy.

Then, to elevate the outfit even more, she adds a stunning pair of deep red suede slingback heels. The perfect pop of fall color!

I’d wear this classy combination for a date at a museum!

a pop of snakeskin.

Woman wearing black jeans, snakeskin booties, a utility jacket and a scarf. — @emmahill

get the look:

Hopping around town on your chilly date night? Nothing is better for cold weather than a shearling utility jacket and a chunky scarf.

This date night outfit on Emma is timeless and chic, but the addition of the snake print booties spices up the look just enough! Adding printed boots to your outfit is a perfect way to elevate neutral basics.

Perfect First Date Looks for Fall

On a first date in 2024, it’s best to aim for a simple, yet elegant outfit. This year has been all about timeless neutrals so go with jeans, heeled ankle boots, neutral tops, and uncomplicated pieces.You’re already nervous enough on a first date, you don’t want to be overthinking everything you’re wearing. Read on for my favorite first date outfit picks.

sweater dress + low heels.

Woman wearing a black sweater dress and Chanel-style block heel pumps. — @ewelinakanty

get the look:

I always love a black sweater dress, but I especially love the look on a first date. This outfit on Ewelina would be perfect for a happy-hour date after work.

In this ensemble, you’ll look polished and put together without looking like you spent the entire night before concocting the perfect outfit (my lips are sealed)!

go monochromatic

black woman wearing an all black outfit with jeans, boots, a turtleneck, and coat for a date night in the fall — @brenna_anastasia

get the look:

I love a good monochromatic look – and Brenna has created the perfect combo above. And since the cold seasons are the perfect time to wear dark tones, a full-black outfit is a great choice!

A black monochromatic outfit instantly gives off a sophisticated and stylish vibe. The jeans and turtleneck are cool-weather pieces that look so chic together, and the pointed black boots add another elegant touch.

Finish this look by layering an oversized blazer or a black wool coat and you’ll be ready for anything the night sends your way!

suede mini skirt + boots

woman wearing a black top with a suede tan midi skirt and black over the knee boots for a fall date night — @almost_readyblog

get the look:

If you’re going for a look that has a cute and girly vibe – this look from Amanda might be just for you!

Suede skirts and shorts are sexy and stylish pair perfectly with a chic black sweater. Over-the-knee black boots are so gorgeous with a mini skirt, and they elongate your legs while adding some extra warmth.

I would also recommend switching to a cardigan and knit tank instead of the sweater if you want the option of removing a layer in case it gets too hot in a restaurant, bar, or wherever you spend your date night!

I hope these chic fall date night outfits for 2024 have inspired you! Remember, light layers, leather jackets, midi skirts, and heeled boots are excellent fall-friendly pieces. With these looks, there’s no doubt you’ll be commanding your date’s attention, and feel chic and put-together too!