What to wear on a first date in the fall? One of these first date outfits for fall 2023! Whether you favour body-hugging styles with sensual cutouts or a wisp of romance with delicate lace, I recommend you save those date outfit ideas for the second date. You need to look cool and chic on the first date. Sure, you should dress up for the first date, but do yourself a favour and don’t fool the guy with the 2-hour version of you. Scroll down to see the best first date fall outfits and pick the perfect first date outfit that suits your personal style and won’t look out of place no matter where he is taking you to.
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Remember you don’t need to impress him and wear something sexy. I imagine you already impressed him. Otherwise, you wouldn’t be dressing up for your first date right now. Well, unless you are going on a blind date or you are a fashion editor, and you met online, and he has no idea what you wear IRL.
In this case, you might want to wear something more exceptional. Yet nothing trashy. Even though Barbie bimbo style is in fashion for fall 2023, what is more, a key fashion trend and the biggest styling trend, you don’t want to dress like a bimbo for the first date. That is not you.
Given you were pointed to Brunette from Wall Street, your style is more sophisticated, feminine, or chic. Or, in the best case, all that.
Anyway, since you have already impressed him, you need to dress like you normally do. Only appropriate for the occasion, of course.
Here is what to wear on a first date in fall 2023.
THE BEST FIRST DATE FALL OUTFITS
By the way, all the collages and product galleries are hyperlinked and shoppable. You can shop for the perfect first date fall outfit instantly. To shop for the look, simply click on the items you need to build your favourite outfit. Your clicks will take you to the online stores where you can purchase the selected item.
CHIC FALL FIRST DATE OUTFITS FOR A DAYTIME DATE
Ease your way back into dating with chic pieces that do all the heavy lifting for you.
From streamlined minimalism to complex detailing, welcome to an array of options to dazzle and charm.
Sleek and tonal is the perfect way to go. Keep things simple yet striking. Show him you are cool, low maintenance, but always put together effortlessly.
1 BLACK BLAZER WITH CARGO PANTS AND BOOTIES
Easy options will immediately get you back into the flow. Perfect for the first date, good cargo pants can be styled in endless ways with a black top to suit the occasion. Whereas a black blazer makes a seamless transition from a daytime casual first date to a casual dinner.
2 OVERSIZED BLAZER WITH LEATHER PANTS AND ROCKSTUD PUMPS
True, a turtleneck is normally a no for a date. But hey, he is taking you on a coffee date. POV A coffee date is not a date – tiktok dating experts say you should not consider a coffee date a date no matter what. He should at least buy you an ice cream.
Even so, you might want to pair your new turtleneck with leather pants and an oversized blazer, in case he takes you from coffee date day to dinner at the restaurant later on. You know you won’t say no if he turns out to be very nice.
CUTE FIRST DATE OUTFITS FALL FOR BRUNCH
Dressing up for a brunch date comes with its own set of rules. Moreover, if it’s your first date.
You don’t want anything shimmery or too opulent, as you normally would for a fancy brunch date. But it is still important to look cute.
Here are two cute first date fall outfits for brunch date that are cute but not too much.
3 SHORT SKIRTSUIT WITH BOOTIES
We favour short silhouettes in black that really sing. Consider how fabrics look in daylight for choices that stand out without feeling out of place.
Style with cowboy ankle boots for the cute fashion girl look.
4 SHORT PANTSUIT WITH ANKLE BOOTS
On the other hand, if you are looking for a novel twist, try a shortsuit with a headband and booties.
We love a combination of ruffles, and buttons to add a fabulous touch to the outfit for the occasion.
CASUAL FALL FIRST DATE OUTFITS FOR A WALK
Don’t opt out of a chunky sweater and sweatpants if a sweater and sweatpants are what you normally wear if he asked you out for a walk – but I hope you do.
5 CARDIGAN SET AND LEATHER PANTS WITH FLATS
A sweater is a no no for a first date, so better wear a cardigan. Fine detailing adds a fabulous touch to a cardigan set paired with leather pants and luxury flats.
Embrace elegance with modern practicality. After all, style isn’t here to weigh you down; it’s here to give you confidence.
Extra tip, make your hair smell extra sweet. I added one of my favourite hair perfumes in the product widget below.
6 DOUBLE BREASTED BLAZER WITH BLUE JEANS AND SNEAKERS
Unlike a sweater, jeans are acceptable. Plus, they work well with a blazer to make an impact. POV I especially recommend this first date fall outfit for corporate girls who live in a suit. It’s the best glimpse of what he will get when dating you. But it’s also casual and great for a walking date.
STYLISH FIRST DATE OUTFITS FOR A DATE AT THE BAR
It’s always a fine balance between looking sexy and showing too much on a first date, but these two stylish first date outfits get it just right.
Capsule and chic, they will let you stand out with quiet elegance.
7 RUFFLED BLOUSE WITH LEATHER PANTS AND HIGH HEEL MULES
Leather pants are well suited for a date at the bar. Pair them with a pretty blouse in soft shades to lighten your face and keep the atmosphere mellow and relaxed. POV A pretty pink blouse will also make you look more approachable and easy to talk to.
8 LEATHER JACKET WITH GREEN DRESS AND SLINGBACKS
If you are looking for a feeling that is a bit more fun, it’s time to embrace the playful feel of short styles.
Going mini makes everything more lively. But tone down with rich shades of berry or green. You don’t want to bring an extra dose of sass to the first date. Layered with a leather jacket to look cool.
ELEGANT FIRST DATE OUTFITS FOR A DATE AT THE RESTAURANT
If you really want to impress, and take his breath away, make his heart skip a beat, you might want to put on a hip hugging cutout dress – I advise you not to, though. But you can never go wrong with a little black dress.
9 A LITTLE BLACK DRESS WITH BLAZER AND PUMPS
Quietly elegant, a little black dress with a blazer and heels is a simple date outfit you can’t go wrong with.
After all, shades of classic noir are the perennial answer to effortless elegance. Don’t forget to add a pretty scent.
10 RUFFLED BLOUSE WITH SHORTS AND HIGH HEELS
For the romantic in you, choose an elegant blouse in a dreamy colour paired with pleated shorts and fancy pumps. Not too high, obviously, if you can’t walk in heels. You don’t want to embarrass yourself on a first date. But on the other hand, you might just want to show him what he will get. If he can do with it, he is marriage material. POV Tiktok dating advice.
FAQ FIRST DATE OUTFITS FALL
If you are feeling overwhelmed by choice and still deciding between two first date outfits for fall 2023, go through FAQ – it will help, for sure.
It depends on where he is taking you, but one of these first date fall outfits will be perfect, for sure.
You can’t go wrong with a little black dress with a blazer, or with the second dinner date outfit presented in this article.
Cardigan set with leather pants and flats, a blazer with jeans and sneakers, or cargo pants and booties. Check the best fall outdoor first date outfits presented in this article to get a clue.
Yes, jeans are ok for a first date in fall – for women. Check the best first date fall outfit with jeans in this article.
For fall 2023, a blazer with cargo pants and booties. See the outfit – it’s presented in this article.
You can wear cargo pants for the first date in fall 2023 (women only, though) – cargo pants are in fashion this season.
The first date fall outfits presented in this article say you are chic and cool, low maintenance but always looking impeccable. Romantic, yet never a drama queen. Elegant and classy, but never boring or desperate.
An oversized blazer with a turtleneck top and leather pants with kitten heel pumps.
One of the two cute first date fall outfits presented in this article.
A pretty blouse and leather pants, or a leather jacket and a short dress. See the first date fall outfits presented in this article for more inspiration.
Only for a hiking date!
A chic performance jacket, black leggings and hiking shoes. Remember you need to dress for the location.
THE BEST FALL DATE OUTFITS FOR THE SECOND DATE
Now that you have picked your first date outfit, you better check the second date fall outfits immediately. More dates will follow!