16 Fall Date Outfit Ideas 2021

Last fall I sat down and put together sixteen different outfits for the most popular fall dates. To my surprise, the post went crazy viral on Pinterest and to this day, is one of my most popular blog posts. Every season since I’ve put together one of these posts and suddenly, we’re back to fall again!

So today I’m sharing an outfit idea for each of your most requested occasions: the pumpkin patch, apple picking, haunted houses, and more. Keep in mind that a lot of these outfits could work for various occasions so feel free to mix and match them! As always, I am leaving direct links to each item so you can shop. I hope you enjoy!

Picnic

Picnic dates were without a doubt one of the most highly requested fall dates. For this outing, I’d go for something super casual. A sweater and jeans work just fine for this afternoon outing. For shoes, I’m keeping things casual with a pair of slip-on mules. These brown ones are from Dingo and are my fall go-to.

Outfit Details— sweater: SheIn, jeans: Express, shoes: Dingo, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Apple Orchard 

There’s something about a good apple orchard outfit… it makes fall feel a little more complete. You’ll notice that a lot of these outfits include a simple sweater and jeans combo. Thankfully I have a gazillion of each so I’m sharing all my favorites with you today. This chunky ivory sweater has a bit of texture to it and easily tucks into a pair of skinny jeans.

I know straight legs are trending right now, but sometimes a pair of skinny jeans are needed. These tuck so easily into lace-up combat boots. I just got these from Bernardo and although they are crazy expensive they are so comfortable + the best quality. I added a hat to spice up the look and couldn’t love this outfit more.

Outfit Details— sweater: SheIn, jeans: Express, boots: Bernardo, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa, hat: Lack of Colors

Indoor Baking/Movies (fall night in)

Baking cheap Halloween cookies + watching a movie curled up on the couch sounds like my kind of night-in. This is my go-to outfit for lounging around the house. My Aerie crossover flares are the most comfortable pants ever. They make your waist look so tiny and your butt extra perky. I almost always slip into them with a simple black tee.

Of course, I’m layering a flannel over top. Not only do these make an outfit a little cuter but the added warmth is a bonus! For shoes, you can always find me sporting my Koolaburra slippers. They are the coziest!

Outfit Details— flannel: SheIn, top: SheIn, pants: Aerie, shoes: Koolaburra by Ugg, earrings: SheIn

Fall Festival 

Fall festivals are the perfect excuse to wear a trendy outfit! For that reason, this burnt orange sweater vest is perfect. I love this piece because unlike most sweater vests it has a cowl neckline rather than a deep v. It’s perfect on its own but could work with a long sleeve layered underneath too.

I’ve got it front tucked into my favorite pair of jeans at the moment. I love this straight-leg fit + the rips in the knee add such a fun element to them. My boots are new from Steve Madden and are the best. They are the perfect neutral color to match my hat + have a heel height that’s super comfy for everyday wear.

Outfit Details— sweater: SheIn, jeans: Lulus, shoes: Steve Madden, hat: Lulus, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Dinner Out 

Of course, grabbing dinner is one of my favorite date nights. Talk about being a major foodie at heart… I think leather pants are the perfect option, especially for a fall date. They aren’t too dressy but they are definitely a step up from a boring ole pair of jeans. I love this chocolate brown for the fall!

I’m keeping things simple with just a solid white long sleeve bodysuit. These tuck so well into straight-leg bottoms and have a classic neckline, allowing this to be worn for every occasion. I’m layering on gold jewels and calling it a day.

Outfit Details— top: Express, pants: Beginning Boutique, shoes: Chinese Laundry, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Brewery 

Admittedly, I’ve never been to a brewery but I imagine they’ve got a pretty relaxed vibe all around. For that reason, a chunky cable knit sweater and a pair of jeans feel like just the right outfit. I’m wearing those same Hutch boots from the earlier outfit and throwing on a cute baguette bag.

Outfit Details— sweater: SheIn, jeans: Lulus, shoes: Steve Madden, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa, purse: Princess Polly

Corn Maze

Corn mazes are always a blast! Because you’ll be walking around for some time, a comfy outfit will do just fine. Here, I’ve got a pair of Spanx faux leather leggings. I wear these nonstop in the fall with sweaters and flannels layered over top. This is my favorite way to keep warm and it never fails.

I’ve had this flannel for a year now and it’s definitely my most worn piece. I reach for it all the time and it’s held up great! My shoes are cutie combat boots from Franco Sarto. Not only are they comfortable for walking longer distances but they have a little extra height to them which is a plus!

Outfit Details— sweater: SheIn, button up: SheIn, leggings: Spanx, shoes: Franco Sarto, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Haunted House 

You can’t go wrong with a good ole striped sweater. I love how oversized this one fits, especially with a pair of black ripped skinny jeans. I’m slipping into my current favorite Chelsea boots also from Steve Madden. These have a higher shaft and work best with skinny jeans + leggings. Of course, haunted houses are typically at night so I’d pop a cute black puffer coat over top of this to finish off the outfit.

Outfit Details— sweater: SheIn, jeans: Express, shoes: Steve Madden, earrings: SheIn

Wine Tasting 

Wine tastings are all the talk now that my friends are beginning to turn 21. For this occasion, you’re likely going to be outside for a chunk of it so a cute turtleneck will keep you cozy. This orange is the perfect fall color and came in a four-pack!

I tucked this into my new favorite straight-leg jeans from Express. I’ve finally found a pair that fit my waist + butt perfectly. I also love the length of these because they can be worn with a heeled bootie. These are another Franco Sarto pair—I have them in two colors and they are my favs. Throw on a felt hat for a photo op.

Outfit Details— sweater: SheIn, jeans: Express, shoes: Franco Sarto, hat: Lulus, purse: SheIn, earrings: SheIn

Coffee Date 

Coffee dates call for something cute yet casual. Just a basic tee will do, with a corduroy button-up layered over top. I wear this duo all the time. I’ve got on a pair of cropped flare jeans and my go-to neutral mules to finish off the outfit. This is also a favorite when I’m headed to class.

Outfit Details— top: H&M, button up: SheIn, jeans: Express, shoes: Chinese Laundry, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Pumpkin Patch

The pumpkin patch is without a doubt the most popular fall date idea. Let’s be real, this could be a girl’s day activity too! Again, a sweater, jeans, and a pair of booties are a never-fail for this occasion. To get in the fall spirit, I’m reaching for a sweater with a little bit of orange in it! Of course, no outfit of mine is complete without that nude hat. I’ve had it for years now and am convinced that every outfit looks better with it.

Outfit Details— sweater: SheIn, jeans: Express, shoes: Steve Madden, hat: Lulus, earrings: SheIn, bracelets: Ana Luisa, rings: Ana Luisa

Drinks

Your outfit for drinks doesn’t have to be boring! Truthfully, this is very similar to what I’d wear out to school here—with the exception of the shoes. For a date, I’d wear nude heels but for the frats, I’d go for sneakers since they’ll get dirty!

I actually have this mesh corset top in several colors and I’m obsessed. It is so flattering and looks amazing on so many different body shapes. Because it’s a bit more fitted, go for a baggier bottom to help balance out the look.

Outfit Details— top: SheIn, jeans: Express, shoes: Target, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Drive-in

Drive-in movies are so popular in some states. We have one right down the road from my school but nobody has ever wanted to go! It’s on my list though. When sitting in the car, something super comfy is necessary. Truthfully just a tee shirt and my Aerie crossover leggings are what come to mind. In true McKenzie fashion, I’m layering a cozy flannel over top.

These sneakers are my new favs. If you’re looking for the platform Converse but can’t find them in stock, you have to check out this Steve Madden version. They go with everything and are super comfortable. Just be sure to size up half a size!

Outfit Details— button up: SheIn, tee: Aerie, leggings: Aerie, shoes: Steve Madden, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Museum 

A museum date would be so fun not only in the fall but any season, really. Although I’d likely still stick to my jeans and sweater combo, this time around I’d spice things up by reaching for flares instead. Fashion Nova is where I get all of my flare jeans. They hug your butt beautifully and make your legs look milessss long.

This sweater is from there as well. Because I can’t link Fashion Nova through LIKEtoKNOW.it you’ll have to go directly to their site to find this.

Outfit Details— sweater: Fashion Nova, jeans: Fashion Nova, shoes: Franco Sarto, earrings: SheIn, necklaces: Gorjana, bracelets: Ana Luisa, brings: Ana Luisa

Hike 

A hike to see the fall foliage is another fun date idea, plus it’s free! It should come as no surprise that I’d wear my Aerie crossover leggings and one of their cropped cami bras. I have them in so many colors and reach for them allll the time. Obvi temperatures are cooling so a cute workout zip up (I left all mine at home) or a flannel layered over top is perfect.

My sneakers are Adidas ZX Boosts. I get questions on them all the time and they are seriously the best. Super comfortable + are the perfect mix of trendy yet still functional for the gym/athletic activity.

Outfit Details— top: Aerie, button up: SheIn, leggings: Aerie, shoes: Adidas

Bonfire 

Bonfires are another popular fall favorite. I’d keep things cozy for this in leggings and a hoodie. If you’re feeling fancy you can pop a shacket over top. For shoes, I’m in my combat boots but sneakers would work just fine for this too! Honestly, anything goes since you’ll end up stinky by the end of it anyways.

Outfit Details— sweatshirt: Aerie, button up: SheIn, leggings: Aerie, shoes: Franco Sarto, earrings: SheIn, rings: Ana Luisa

pin this post to refer back to before your big outing!

My date night posts are among the most popular I share here on styledbymckenz.com. For that reason, I’ll be back next month to share 16 outfits for winter too. I had so much fun putting this post together and hope this gave you a bit of outfit inspiration for your next fall outfit!

With love, McKenz

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