Last Updated on 14/03/2022 by Rashi
Read: date outfits but make it cute TikTok trends x runway chic
Picking an outfit is already difficult, and if it’s a date outfit it gets more annoying. And then you go to Pinterest or Google and search ‘date outfit inspo’ but it just gets even more annoying because the outfits suggested just do? Not? Understand? the assignment?
And when the weather doesn’t cooperate?
Oof I get it.
Ngl though, this post was the same as other ones -a mix of different date outfit ideas. But then I thought it could be more helpful if outfits were categorized into types of dates and outfits for all kinds of weather.
Anyway, you can stop panicking now.
Cute Outfits to wear on Café/shopping dates
1. Shirt dress with crew neck
Crew necks are the cutest layering pieces for fall, and the most trendy way to style them is by pairing them with a shirt dress. You can pick casual linen, knit, or polo as per your date or vibe.
For a dressier style, pair the look with strappy square-toed shoes or mules; for a more casual approach, pair it with chunky boots and sneakers. Adding pearl jewelry and/or a bucket hat to the outfit would make it even more Instagram-worthy!
Check Out: How to style oversized sweaters for fall

2. Teddy coat and knits
Winter outfits have their own charm and that’s textured materials and classic pieces like woolen long coats, flimsy faux leather trenches, and cute knits. Pair different textures together for a creative and cute outfit.
3. Denim on denim
Denim on denim looks like it leans more towards street style fits than cute date outfits – but hear me out.
Style denim minis and oversized denim shirts with statement color or soft pieces like pastels and blouses. To add some spice to your outfit, accessorizing is the key. Add as many accessories as your outfit can handle. If your aim is for an urbane-chic look, go for modern chains or baroque pearls. Traditional pearls and elegant gold is best for a sweet look.


4. Sweater vest over a collared blouse
We already have seen a rise in academia aesthetic outfits. And we are styling outfits for dates… so romantic academia -yay or nay?
Pair a collared (also a bit oversized) blouse with a sweater vest for an academia-inspired date fit. You can also add in reading glasses for the vibe, or make it look more on-trend with leather bottoms.
Picnic/garden dates or watching sunset together
1. Cardigan with a slip dress
Cozy outerwear pieces like cardigans can be worn with almost everything and look super cute. While slip dresses look effortlessly chic and romantic. Talk about a better date outfit combo huh?
2. date outfits with cute summer dresses
If you’re aware of the global street style scene and TikTok trends, you know that fall-winter doesn’t mean the end of the summer dresses era. Wear a turtleneck under a slip or strappy dress to your date if the day is chilly.
For a more creative and cute date look, style outfits with a burst of color or monochrome combo. For fun and flirtatious look, add a bucket hat and beautiful hair clips to the look. To make the fit look more polished, you can wear it with mules and a quilted bag.


3. Oversized cardigan and pleated skirt
Tuck an oversized or chunky cardigan in a pleated or a tennis skirt. Style the combo with cute accessories, such as bucket hats and beaded jewelry, for THE soft girl aesthetic date outfit™.
4. Gingham dress and cute sweaters or cardigans
When someone says picnic, isn’t gingham print comes the first to come in mind?
If it’s cold where you are a bulky sweater would be best to style it with and if it weather allows it you can just layer a light cardigan over it.


Art gallery/museum visits
1. Faux leather blazer with a baby tee
Crop polos and baby tees with minis were on Instagram feeds all summer and fall versions would include a faux leather blazer as well. If the combo feels too casual for your date, pair a knit skirt and pearl necklace.
2. Turtleneck layered under a button-up

I don’t know if your Pinterest or Instagram newsfeed blessed you with this layering – but here’s another academia look for your date.
Style the turtleneck and button-up combo with a denim skirt or straight-leg jeans.

Check Out: Light Academia outfits to style in fall-winter 2022
3. Polo dress with a blazer
Considering polo dress popularity and how versatile and cute it is, it would’ve felt illegal not to include it in the list of date outfits.
You can style a cropped blazer if you prefer to keep your looks gossip girl-friendly.
You can style one with chunky boots and a shoulder bag for a y2k look.
Or you can style a relaxed blazer layered over the dress for classic fall street style.
Brunch or lunch dates
1. Knit tops with leather pants
A knit top and leather pants are the ‘IT’ girl combo you don’t wanna miss. I definitely couldn’t!
Knit tops can also be worn under blazers (crop or oversized to dress) to add a layer in outfits or dress up. Other than shoes the ensemble doesn’t need much else. But feel free to go crazy over accessories if you want!


2. Ankle length knit dress + accessories
An ankle-length knit dress is one of the most sophisticated but cute date outfits. You can dress the classiness a bit down with chunky boots or sneakers, and layer it under an oversized shirt. Or you can up the game with a structured blazer or a trench coat. Throw in some jewelry and you’re done!


3. Trendy prints
For 2022, think of 70s swirls, checkerboard, geometrical prints, tie-dye in bright colors, groovy pattern, marble print, polka dots, leopard print, plaid and florals (that are always in).


Check Out: more brunch outfits for your date in 2022
Dinner or fancy dates
1. Monochrome outfit
The easiest way to style date outfits is to pair cute pieces in one color together. You can either choose to style pieces in exact same color or in different shades and tints. Start by picking up the main piece of your outfit, and then pick other pieces from the same color family. If you’re feeling bold, you can throw in a neon piece as well. Monochrome outfits also don’t have to be all solids – get creative with your prints!
2. Sheer outfits for cute date pictures
Metal mesh, skin-fit risqué mesh in edgy prints, and contrast to both, romantic mesh ruffles! There’s something for everyone when it comes to sheer. If you aren’t into baring skin there’s def many others ways to wear sheer. One of the best solution is getting chic sheer gloves.


3. Tailored Suit or set
What’s more chic, dinner-appropriate and fashionable than a tailored suit? Whether you prefer tailored or tweed skirt suits or cropped and asymmetrical set or a polished blazer and pant suit, its one of the best dinner date outfit idea!
4. Fur and leather

Need I say more?
At home dates
1. Denim midi skirt with cozy sweater
And who says comfy and cute always gotta be sweats and bucket hats? More of coffee break fits than cute date outfits anyway… Besides, didn’t we leave lazy fits in fall 2020?
Denim midi skirt is a minor trend you need to hop on right now and style it with your fav cozy sweater. Effortless, cozy, and cute!

2. Cozy knit set
If you don’t feel like dressing up for a movie marathon date but still wanna look cute, a knit set would be the best pick! Some are not exactly as comfy as a lounge set, but I say oversized ones are definitely cloud-like.

3. Chunky cardigan and ribbed pants
I’ve probably mentioned cardigan more in this blog post than “cute date outfit”. But can you blame me if they are not just super cute and trendy but also top tier comfy? And also versatile?
Paired with ribbed pants, it’s a combo you can wear on not only stay-at-home dates but also for casual lunches, coffee runs, groceries, movies, and shopping. It all depends on how you accessorize and what pieces you pick.

