Fall date outfits 2025 for all of you who have no idea what to wear for a date in fall – this fall. But also some trendy fall date outfit ideas for all of you wondering what to wear for a dinner date at a fancy restaurant. But also stylish fall date outfits for day dates. All in all, going out for a walk is still popular, too. Unlike staying in and having a fall date night at home. Although, I did put together some outfits for a date in, also. After all, the date night doesn’t have to end as you get to your home door. It’s then and there when you need to impress even more! Anyway, scroll down to see some of the most fashionable fall date outfits for fall 2025.

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Have no idea what to wear on a date in the fall? I give you several! For everyone aged in between 16 and 65. All in all, I am here to help you dress up for a fall date no matter where your guy/them/girlie is taking you. And he/they/she might take you to a very special place since dating options are not limited anymore. *I will use male pronouns from now on to make writing/reading more fluent – but we are inclusive.

Luckily, I can identify all the fall date ideas that might pop up in his mind when thinking about how to impress you.

And I know exactly what you should wear to a date he is taking you. Here are some stylish fall date outfit ideas 2025 and fashionable fall date outfits 2025 to try for your next date. For a date night or a day date.

Yes, I put together some stylish and effortless fall date outfits that are just perfect for a date on a cold autumnal night or a day date on a sunny day in fall 2025.

Anyway, scroll down to see what to wear to date in fall 2025!

THE BEST FALL DATE OUTFITS 2025

Ps. All the fall date outfit ideas you can pick up in this article and fall date outfits you will see here are shoppable directly. The product galleries and collages are all hyperlinked. To buy the fall date outfit that you want to wear to your next fall date in fall 2025, simply click inside the pink brackets that show up as you touch the collage.

Once you touch/click on the item you want to buy quickly, a store window will open, and you will be able to purchase the product you have clicked on at once.

Sounds easy, right? Now scroll down to find out what to wear for a date in fall 2025.

*And to learn more about the size and fit of the clothes/shoes featured, subscribe to Brunette from Wall Street Substack. I’m sharing clothes/shoe reviews with free subscribers, too.

FANCY FALL DATE OUTFITS FOR THE FIRST DATE

First, stylish fall date outfits you can wear for your first date ever.

Ps. Once you pick a fall date outfit to wear to the first date, scroll down and save/shop at least one more fall date outfit. Trust me, more dates will follow soon.

He will ask you for a second date if you wear one of these fall first date outfits, for sure.

1 MINI RETRO DRESS AND COMBAT BOOTS WITH OVERSIZED BLAZER

For the first date, the first official day date or the unofficial date, you should wear something cool, but classy, but cool – like a mini retro dress with combat boots.

Turn to minimalist classics when you want to look nice, but not like you made too much effort.

While a mini dress will enhance your feminine side, the combat boots will make you look cool. And boots will keep him guessing whether you can walk in heels – if he is curious, you already have your invitation to the second date.

2 BLACK JACQUARD BLAZER ON SHORT WRAP DRESS AND POINTY KITTEN HEELS

Well, if you need a bit of height, put on kitten heels. Kitten heels are some of the most fashionable fall 2025 heels and the best shoes for the first date. There is something quite sexy yet sublime about the kitten heels.

3 LEATHER JACKET WITH SHORT SKIRT AND KITTEN HEELS

For a casual date night or day date, style your new mini skirt with a leather jacket (the 20216 staple look is a key fashion trend for AW25/26) and a turtleneck if it’s just an ice cream date.

POV, a turtleneck is a no for a romantic date. But a quick ice cream date is not a proper date either.

4 DOUBLE BREASTED BLAZER WITH MINI SKIRT  AND BOOTIES

Mid-heel booties are a great choice for the first date in fall, also. Put on cool rock chic booties and style them with a little uniform for a cool yet fancy look.

Go all out in cute skirtsuit outfit that offers a fashionable solution to a daytime affair.

FALL RAIN DATE OUTFITS

It will rain on your second date, so you better check these fall rain date outfit ideas before you cancel your date. These fall rainy day date outfits are waterproof but cute.

5 TRENCH COAT WITH A DRESS AND PATENT LEATHER PUMPS

A trench coat will keep you dry as you dance the night away in the rain, so it’s the perfect time to invest in a quality trench coat.

For something a bit different, style your new trench coat and matching dress with patent leather pumps.

And make sure you forget the umbrella. It’s a good test to see if he is a gentleman. POV I added some hair pins to this date outfit to keep your hair looking good, in case he is not a gentleman. This way, you will go home looking fabulous, ready to meet someone better.

6 TRENCH COAT WITH DARK JEANS AND PATENT LEATHER KITTEN HEELS

Obviously, you can wear something more casual for a movie date or day date.

A trench coat with a nice silk top and dark jeans paired with kitten heels will be a great choice. This date outfit is effortlessly chic and cute.

CAPSULE FALL DATE OUTFITS

If you are going on dates only when the weather is nice and warm (read not often), you might want to see capsule fall date outfits you can always rely on, next. All in all, these fall date outfits never go out of style, plus they will always look good on you.

7 DOUBLE BREASTED BLAZER ON A BLOUSE AND LEATHER PANTS  WITH KITTEN HEELS

When going out on a dinner date straight after work, make life simpler with leather pants and kitten heels.

A pair of leather pants for the evening is a chic answer for when you want to look fantastic and feel sexy but cool. Perfectly matched with a blazer and kitten heel pumps you will make an appearance no matter where he is taking you.

8 SHORT RED DRESS WITH HEELS AND A HEADBAND

Streamline your datewear with alluring silhouettes in bold and rich colours. *Make sure you pick the right heels. You know, kitten for morning, mid heel for noon and high heels for late afternoon.

9 LITTLE BLACK DRESS WITH PUMPS

Or simplify your eveningwear with a little black dress.

Fitted around the bust and waist with the volume at the hem, a little black dress lets you stand out with quiet elegance.

*Give your little black dress a modern update by a chic hair cut (it’s time you get bangs) and designer shoes that stand out.

TRENDY FALL NIGHT OUT DATE OUTFITS

Now, a few trendy fall date outfits 2025 – the most fashionable fall outfits of 2025 that signal confidence. POV Tacky is trendy for fall 2025.

10 MINI BURGUNDY DRESS WITH PINK PUMPS

Fall winter 2025/26 is all about burgundy and ruched dresses. Sexy, alluring, cute, tight, and pomegranate are the key words this season.

11 MINI BLACK TWEED DRESS WITH DRESS BOOTS

Mini lengths are perfect for reducing the bulkiness of layers and really showing off those new boots you invested in.

CUTE FALL LUNCH DATE OUTFITS

Going mini makes everything seem more lively, especially if you add in an extra dose of popping colour or fashionable hair accessories.

12 DOUBLE BREASTED BLAZER WITH MINI PLEATED SKIRT AND KNEE HIGH BOOTS

Cute and fashionable, we are obsessed with mini pleated skirts this fall. Maximise on the appeal of the new academia styling trend with double breasted blazer and knee high boots when you are putting together cute fall lunch date outfits 2025 for lunch with your fiancé.

CASUAL FALL DATE OUTFITS 2025 FOR A CASUAL DATE

A cute mini skirt is undoubtedly the outfit that will make your guy’s heart skip a beat. It’s sexy and so fashionable for fall 2025. Pair with trendy Adidas Samba sneakers for a walk date. Ruffles balance out the casual nature of the sneakers to provide elevated options that hint at fun times to be had.

13 BLACK SLIK BLOUSE WITH DARK WASH JEANS WITH SNEAKERS

But for when he says that there is this cool new place in the town and you can go and check it out with him if you want (Oh, boys! Who can understand them, right?), just put on this outfit and keep it cool.

Yes, you can wear jeans and sneakers to a date if it’s a casual date. But go for a chic slik blouse and jeans outfit for a casual date in the city.

14 BLAZER WITH DARK WASH JEANS AND BOOTIES

Simple and chic casual fall date outfit, indulge in a mix of daytime fabrics with intoxicating pops of houndstooth. Whether he is taking you to the movies or on an ice cream date, this option will have you ready in no time.

FALL OUTFITS FOR PICNIC DATE IN FALL

If you are looking for a feeling that is less about formality and more about fun, it’s time to embrace the playful feel of short, sassy boho styles.

Short lengths in bright colourways or bohemian prints are well suited for more casual occasions – like a picnic date.

15 BARN JACKET ON SHORT BOHO DRESS WITH WESTERN ANKLE BOOTS

Paired with western booties and layered with a barn jacket, a short boho dress will be the best outfit choice for the occasion.

Look for easy silhouettes to help keep the atmosphere mellow and relaxed.

ROMANTIC FALL DATE NIGHT OUTFITS

When the sun comes down and you step out of the hot air balloon (IMAO, a short trip with a hot air balloon is the most romantic date idea), it’s time to put on a pretty dress and bring romance to a new level with some precious pumps.

16 LONG LACE ORANGE DRESS WITH HIGH HEELS

Opt for some feminine elegance with a lace dress in the colour that suits everyone.

SEXY FALL DATE OUTFITS FOR A DATE IN THE BAR

If you are going out for drinks after work, you might want to only upgrade your workwear for the night out.

17 BLACK PANTSUIT WITH HIGH HEELS

You can easily upgrade your sleek black pantsuit with a precious or fashionable hair accessory, bold lipstick and a spritz of perfume. Maybe a different bag – your new shoulder bag you have been hiding in your desk drawer (POV If you don’t have it yet – browse through the widget below, click and go to the store and buy it today – it’s one of the three most wanted bags at the moment). It’s these details that make you shine without stressing too much.

18 PRETTY DRESS WITH PRETTY SHOES

A mini dress is for sure the best seductive option for a date night. Put on stunning heels, and you will be out in less than a minute.

FALL COCKTAIL DATE OUTFITS

For a date in the opera, go glam head to toe. Seize the chance and wear a cocktail dress or something truly spectacular. A great dress takes the guesswork out of dressing up, just step into a pair of statement shoes, and you will be out the door in no time.

19 LONG SLEEVE MIDI DRESS WITH PRETTY STILETTO SHOES AND A TIARA HEADBAND

For the moments when elegance is demanded, the long and slim proportions of a little black dress can be a perfect option.

Extra details, such as ruching around the waist, will help the silhouette feel contemporary.

Also, a cutout dress is always a fine balance between looking sexy and showing too much skin, while the mid-length option gets it just right.

20 SHORT SLEEVE COCKTAIL DRESS WITH PUMPS AND A CLUTCH

Look for richness in trendy fall dresses with luxe fabrics and deep tones.

ELEGANT FALL DINNER DATE OUTFITS

The easiest item to throw on for an elegant dinner date is a dress. *Wear with a blazer or jacket for now, and start layering on the coats later in the fall.

Or go for this elegant fall dinner date outfit that is as effortless as exceptional.

21 RUFFLED BLOUSE AND LEATHER PANTS WITH HIGH HEEL MULES

We like leather pants for their versatility as they take you from a work all the way to closing time at your favourite neighbourhood bar.

Pair with a pretty silk blouse for a date night in fall 2025.

POV If you know you will end up in the most popular bar in the town and you really want to be in the spotlight all night, add high heel mules to this fashionable fall date night outfit. Like this!

HOME DATE OUTFITS FOR FALL 2025

If you choose to have a date in, revel the luxurious feel of head-to-toe knits or slinky silk.

23 KNIT DRESS WITH POINTY FLATS

A stylish knit dress will keep you looking fabulous right up until bedtime.

FAQ FALL DATE OUTFITS 2025

If you are feeling overwhelmed by choice and can’t decide what to wear to a date tomorrow, I made a comprehensive list of delectable options for date night. Go through the FAQ – it will help, for sure.

THE BEST FALL DATE OUTFITS 2025 YOU CAN ALSO WEAR IN FALL

True, I didn’t show you how to dress for a brunch date in fall 2025. Check fall 2025 brunch outfits next. Ps. You might also want to see winter date outfits.