An autumn afternoon sounds like the perfect time to go on a date. When the leaves start to drop colorfully and the pumpkin spice lattes start to brew, it’s hard not to feel the romance in the air.
If you’re going on a date, try these casual date outfits for fall and you’ll look chic.

Whether your ideal fall date involves bike rides and hiking as you take in the autumn foliage, visiting a cidery or winery.
Or having a movie marathon at home, visiting a farmers’ market, an amusement park, going on a picnic, or a restaurant date, there are chic ways to dress up for such a casual date without overlooking your style and comfort.
See The Contents
- 1 Casual Date Outfits For Fall To Look Chic
- 1.0.1 1. Oversized Cable-knit Sweaters & Denim Jeans
- 1.0.2 2. Denim Jeans & Jackets
- 1.0.3 3. Oversized Hoodies & Ankle Boots
- 1.0.4 4. Oversized Sweater Dresses & Boots
- 1.0.5 5. Sweater Vests & High Heels
- 1.0.6 6. Chunky Sweater & Shorts
- 1.0.7 7. Chunky Sweaters & Leather Pants
- 1.0.8 8. Leather Pants & Blazers/Jackets
- 1.0.9 9. Long Coats & Denim Jeans
- 1.0.10 10. Fall Coats & Leather Leggings
- 1.0.11 11. Cargo Pants & Stilettos
- 1.0.12 12. Long Skirts
- 1.0.13 13. Summer Dresses & Boots
- 1.0.14 14. Blazer Dresses & Long Boots
- 1.0.15 15. Rock Bodycon Sweater Dresses
- 1.0.16 16. Miniskirts & Long Boots
Casual Date Outfits For Fall To Look Chic
Since fall is more romantic than you think, here are chic date outfits to rock all fall:
1. Oversized Cable-knit Sweaters & Denim Jeans



This pairing of an oversized cable sweater and denim jeans, whether blue-wash, black, or grey, is proof that a safe casual ensemble can still be chic.



If you wish to effortlessly step up your ensemble with a pair of shoes, complement your look with a pair of white sneakers or leather boots.
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A grey knit open cable-knit cardigan and grey ripped jeans paired together are such a dreamy ensemble for those dressers who appreciate ultra-cool styles. Introduce grey leather ankle boots to the mix for an added touch of polish.
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2. Denim Jeans & Jackets

Consider pairing a denim jacket with a jeans-and-a-tee combo for head-to-toe comfort dressing. In the shoe department, go for something dressier by finishing with a pair of black booties.

Choose a leather biker jacket and black skinny jeans for a casual fall outfit with a twist. Let your expert styling truly shine by complementing this look with knee-high leather boots.
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You can also swing into something laid-back yet current with a black jacket and grey jeans. A pair of black leather boots is a savvy option to round off your getup.
3. Oversized Hoodies & Ankle Boots

This casual pairing of an oversized hoodie and pointed-toe ankle booties is a real lifesaver when you need to look great but have no extra time. Complete this ensemble with a cute handbag for a sense of elegance.
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4. Oversized Sweater Dresses & Boots





Try teaming an oversized sweater with over-the-knee boots to create a totally stylish and current laid-back ensemble. Feeling inventive? Change things up a bit by laying atop your favorite coat or blazer.
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5. Sweater Vests & High Heels

If you’re searching for a casual but also absolutely stylish getup for your fall date, wear an oversized sweater vest over a white shirt. Bring an instant sultry vibe to this ensemble by rocking a pair of strappy heeled sandals.
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6. Chunky Sweater & Shorts



For an outfit that’s super simple but can be modified in a variety of different ways, opt for a chunky sweater and leather shorts. Add a pair of brown boots to the mix et voila, the outfit is complete.
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You can also dress a long coat over this look. Black combat boots are guaranteed to infuse an air of sophistication into your look.
7. Chunky Sweaters & Leather Pants



The combination of an oversized sweater and leather pants is extremely easy to throw together and so comfortable to wear a variation of as well! For maximum impact, introduce boots, pumps, or white sneakers to the equation.
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8. Leather Pants & Blazers/Jackets


For a fall date outfit that offers function and chicness, make a blazer or leather jacket and black leather leggings your outfit choice. Finishing off with a pair of fall boots is a good way to introduce a dash of edginess to your outfit.
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9. Long Coats & Denim Jeans








For an edgy and casual outfit, pair a long coat with your favorite pair of jeans — these two items go perfectly well together, no matter your inner layer.
For a modern on and off-duty mix, add a pair of white sneakers or ankle boots to the equation.
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10. Fall Coats & Leather Leggings





For a classic-meets-cool look, wear your winter coat with leather leggings, in your preferred color — think black, brown, or olive green. Let your styling prowess really shine by completing this getup with leather boots or white sneakers.
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11. Cargo Pants & Stilettos


Inject safari-style into your casual fall date outfit by pairing your favorite olive green cargo pants and a well-fitting top. A pair of nude pumps or sandals effortlessly steps up the wow factor of this getup.
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12. Long Skirts

For your casual fall date outfit, go for something classic yet modern with a long olive green pencil skirt and a fitting top. Add open heeled sandals, a fedora, and a purse to the mix and you’re good to go!
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If you’re a fan of relaxed combos for your fall date wardrobe, why not opt for an animal print pleated skirt and a turtleneck top? Introduce a statement belt and ankle boots to your ensemble and off you go looking smashing.
13. Summer Dresses & Boots






Look seriously chic yet off-duty by wearing a floral dress on your fall date. To introduce some extra oomph to this look, complete your getup with leather-heeled boots, and if it’s getting cold, rock a cardigan or leather jacket.
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14. Blazer Dresses & Long Boots

You’ll be surprised at how extremely easy it is to pull together this laid-back look. Just a blazer dress and a statement belt to cinch your waist. Black combat boots are guaranteed to inject a hint of sophistication into this look.
15. Rock Bodycon Sweater Dresses




If you’d like to take your casual fall style game up a notch, opt for a bodycon sweater dress. Finishing off with white low-top sneakers or pointed-toe ankle boots is a guaranteed way to add an air of class to this ensemble.
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16. Miniskirts & Long Boots

This look is indisputable proof that a plaid blazer and a plaid mini skirt are amazing when worn together in a casual getup.
Go the extra mile and jazz up your look by rocking a lace top and slipping into brown leather knee-high boots.
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Ready for your autumn date? Try these casual date outfits for fall!