Brunette from Wall Street what to wear fall date outfits

FALL DATE OUTFITS THAT WILL MAKE YOUR GUY’S HEART SKIP A BEAT TWICE

Fall date outfits 2024 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 2024.

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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 is taking you. And he might take you to a very special place since dating options are not limited anymore.

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 2024 and fashionable fall date outfits 2024 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 2024.

Anyway, scroll down to see what to wear to date in fall 2024!

THE BEST FALL DATE OUTFITS 2024

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 2024, 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 2024.

FANCY FALL DATE OUTFITS FOR THE FIRST DATE

First, a few 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 CARDIGAN SET AND VEGAN LEATHER PANTS WITH POINTY FLATS

For the first date, the first official day date or the unofficial date, you should wear something cool, but classy, but cool – like leather pants and cardigan set and pointy flats.

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

While a cardigan set will enhance your feminine side, the leather pants will make you look cool. And pointy flats will keep him guessing whether you can walk in heels – if he is curious, you already have your invitation to the second date.

2 LEATHER JACKET OVER A MINI WRAP DRESS AND KITTEN HEELS

Well, if you need a bit of height, put on kitten heels. Kitten heels are some of the most fashionable fall 2024 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 and a turtleneck if it’s just an ice cream date.

4 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.

5 BLAZER ON BLUE JEANS WITH SNEAKERS

Yes, you can wear sneakers to your first date. For fall 2024, style sneakers with a chic blazer and casual blue jeans.

6 BLAZER WITH DARK JEANS AND STILETTO PUMPS

A pair of dark jeans 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 stiletto pumps you will make an appearance no matter where he is taking you.

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.

7 TRENCH COAT WITH A DRESS AND PLATFORM 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 navy trench coat.

For something a bit different, style your new trench coat with patent leather platform 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.

8 TRENCH COAT WITH DARK JEANS AND BOOTIES

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 booties 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.

9 LEATHER PANTS AND A BLOUSE WITH HEELS

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

10 LONG SLEEVE DRESS WITH DRESS BOOTS

Streamline your eveningwear with alluring silhouettes in bold and rich colours.

11 LITTLE BLACK DRESS WITH PUMPS

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

TRENDY FALL NIGHT OUT DATE OUTFITS

Now, a few trendy fall date outfits 2024 – the most fashionable fall outfits of 2024 that signal confidence. POV Tacky is trendy for fall 2024.

12 SHORT PP PINK DRESS WITH PINK PLATFORM HEELS

Fall winter 2024 is all about Barbie core and bimbo aesthetic. Sexy, alluring, cute, tight, and pink are the key words this season.

Go all out in head to toe pp pink outfit that offers a fashionable solution to a daytime affair.

13 DOUBLE BREASTED BLAZER WITH A MINI DRESS AND BIKER BOOTS

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

14 STRIPED CARDIGAN OVER CROPPED SHIRT AND MINI LOW WAIST CARGO SKIRT WITH LOAFERS

Cute and fashionable, we are obsessed with mini low waist cargo skirts this fall. Maximise on the appeal of the new academia styling trend with a cropped shirt and a striped cardigan layered over your shoulders.

CASUAL FALL DATE OUTFITS 2024 FOR A CASUAL DATE

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

15 CARDIGAN WITH MINI DENIM SKIRT AND SAMBA SNEAKERS

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 2024. Pair with trendy Adidas Samba sneakers for a walk date.

16 OVERSIZED AVIATOR JACKET ON DARK BLUE JEANS AND SILK BLOUSE WITH NEW BALANCE SNEAKERS

Wait, I have another fall brunch date outfit with sneakers for you. This time with dark jeans and a black silk blouse. This outfit is the best outfit to wear for the “first date”. You know, the first date that is not officially the first date, since he didn’t invite you out on a date with the right words.

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? Anyways, just put on this outfit and keep it cool.

17 BLAZER WITH BLUE 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.

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.

18 BLACK PANTSUIT WITH 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.

19 CUT-OUT DRESS WITH MACH & MACH PUMPS

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.

20 LITTLE BLACK DRESS WITH FEATHERS

Give your little black dress a modern update by adding a feather scarf and pairing your little black dress with designer shoes that stand out.

HOME DATE OUTFITS FOR FALL 2024

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

21 KNIT DRESS WITH POINTY FLATS

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

FALL BLACK TIE DATE OUTFITS

For a date in the opera, go glam head to toe. Seize the chance and wear a gown or something truly spectacular.

22 LONG NAVY DRESS WITH BALLOON SLEEVES

For the moments when elegance is demanded, the long and slim proportions of a lace gown can be a perfect option.

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

23 LONG SLEEVE MIDI DRESS WITH HEELS AND A TIARA

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

24 SHORT SLEEVE GOWN 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.

25 WRAP DRESS AND HIGH HEELS

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

26 RUFFLED BLOUSE AND BLACK LEATHER PANTS WITH HIGH HEEL MULES

We like black 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 2024.

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!

CUTE FALL LUNCH DATE OUTFITS

For a fall lunch date, you can wear something cute – like a tweed skirt suit or shorts. Scroll down to see and shop some of my favourite cute fall lunch date outfits 2024.

27 PINK BLOUSE WITH PLEATED SHORTS AND HIGH HEELS

If you want to take the guesswork out of dressing for lunch with your fiancé, simply put on a pretty blouse and pleated shorts.

Ruffles balance out the more casual nature of the shorts to provide elevated options that hint at fun times to be had.

28 TWEED DRESS AND BALLET PUMPS

A tweed dress with heeled ballet pumps is the ultimate date lunch outfit in the fall. It’s sophisticated and charming. Ps. This fall date outfit is the best outfit for a date with your mother-in-law, also.

29 DOUBLE BREASTED BLAZER WITH TWEED SHORTS AND BOOTIES

For a lunch date with your mom and your sister, you can wear tweed shorts. Banish the thought of tweed as bland and boring. Shorts have never been as sexy as this season when tweed shorts are trending.

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 styles.

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

30 TURTLENECK TOP WITH TWEED SHORTS AND RIDING BOOTS

Paired with riding boots and a turtleneck top, tweed shorts 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

Last but not least, one more romantic date night outfit you can wear for a date night in fall 2024.

31 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.

Ps. Check the fall winter 2024 dress trend report to find more pretty dresses you can wear for a date night this fall.

FAQ FALL DATE OUTFITS 2024

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.

WHAT TO WEAR TO A DATE IN FALL 2024?

A fashionable fall outfit that makes you look stunning and feel fierce.

What to wear on a first date fall?

Something that will make your date’s heart stop a beat. Check the best first date fall outfits for some ideas.

What to wear on a day date in fall?

Long sleeve dresses are a great choice for a day date in fall. However, you have other options, too. Check fall day date outfit ideas in this article to find the best day date fall outfit for your next date.

What should I wear for a date in fall?

A fall date outfit that makes you look ravishing and feel confident! You can find the best fall date outfits in this article.

What to wear on a coffee date in fall?

It depends on who you are getting coffee with. POV A coffee date is not a real date, and you shouldn’t stress much about what to wear for a coffee date with a guy – dress for your own delight. But at the same time, you want to look your best. Check the coffee date fall outfits presented in this article to see what to wear for a coffee date in the fall if you really want to impress your date. Ps. Just make sure you stand far from his coffee cup – he might spill his coffee once he sees you dressed, as suggested in this article. His heart will skip a beat.

What to wear for a lunch date fall 2024?

A classy fall outfit. See the lunch date outfits presented for some inspiration.

How to dress for a picnic date in fall?

It depends on the location. Check the best fall picnic outfits posted on Brunette from Wall Street before you get dressed for your next picnic date.

Can you wear a sweater for a date fall 2024?

No. A sweater is not something you should wear for a date. But a cardigan is ok for a date.

Can you wear leggings to a date in fall?

No, unless he is taking you to the vineyard for wine tasting date. Check the best wine tasting date outfits to see how to style leggings for a date in fall 2024.

What are the best fall date outfits?

Outfits that make you look captivating and look confident, furthermore fall outfits that never feel out of place and add up to your personality.

THE BEST FALL DATE OUTFITS 2024 YOU CAN ALSO WEAR IN FALL

True, I didn’t show you how to dress for a brunch date in fall 2024. Check fall 2024 brunch outfits next. Ps. You might also want to see winter date outfits.