12 cute date outfits you need for fall 2021

Last Updated on 11/01/2022 by Rashi

Read: date outfits but make it cute TikTok trends x runway chic

Fall is in full bloom and I hope so is your love life. If it isn’t well..these cute fits are also perfect for brunches with besties, or uni/school days for when you do not wanna show up in a sweatsuit and unfinished assignment. And if you have nowhere to go, this is your sign to dress up and take bomb-ass pictures with main character energy.

Check Out: Trendy 2021 fall outfit ideas to channel your main character energy

Cute Outfits to wear on your dates in fall

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. Sweater vest over a collared blouse

We already know fall means 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.

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3. 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.

4. 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.

5. 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 2021

6. 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 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.

7. 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.

8. 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!

9. 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.

One of cute black date outfits consisting of black polo dress and black blazer.

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.

10. summer dress over a turtleneck

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.

For a more creative and cute date look, style outfits with a burst of color or monochrome combo. For a 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.

11. 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 outfitβ„’.


12. 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!