22 easy and cute date outfits to try this year

Last Updated on 08/08/2022 by Rashi

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

cute outfit idea for a shopping date or cafe hopping date consisting of oversized sweater over pastel color lilac dress

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.

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

date outfit idea for museum or art gallery visit: cute button up over turtleneck and denim

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.

cute light academia date outfit idea with turtleneck, white shirt and black pants

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!

A style blogger based in India wearing a ribber or knit top with leather pants, style with gold jewelry for cute date outfits.
A south Asian blogger and influencer with jet black wavy hair and golden skin wearing a knit top and talking about cute date outfits.

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).

cute and aesthetic outfits for date with 70s trendy crop groovy jacket, bright red wrap blouse and white jeans.
cute date outfits with red v neck wrap blouse and groovy pattern 70s jacket with white jeans.

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. Fur and leather

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. 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.

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!

A monochrome blue outfit as a part of cute date outfit -consisting of blue knit top, denim midi skirt, fur tote bag and black boots.

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.