16 Fall Date Outfit Ideas

Over the summer I asked what kind of blog posts you wanted to see, and without a doubt, the most popular answer was date night outfit ideas. So, I went ahead and shared 16 summer date ideas + an outfit for each and it is still my most popular post of 2020.

Because you all loved that post so much, I decided to make it a series and share 16 outfits for every season when the time comes. Today’s the day, and I’ve got 16 outfit ideas for your most requested fall activities.

Remember that feeling comfortable and confident in what you’re wearing is key. These outfits may seem a bit dressier than your typical choice but keep in mind that clothes are my “identity” and a huge part of me so obviously I want that to show through. I hope this post gives you some outfit inspiration for your next date or if nothing else, a few date ideas for the fall (even if you are just going with your friends!).

PUMPKIN PATCH 

The pumpkin patch was easily the most requested fall date! Typically people head to the pumpkin patch in late September-early October so I recommend going for a sweater. This button-front cardigan style is so popular this season. They are super versatile because you can wear them open as a cardigan or buttoned up as a pullover.

I’m popping on cropped flare jeans as per usual. These are some of my favorites as they have the perfect amount of distressing. Mules are my favorite transition shoes for the fall; so easy to slip on and they are crazy comfortable! Add statement earrings and gold jewels to accessorize.

Outfit Details— sweater: SheIn, jeans: Express, shoes: Chinese Laundry, earrings: SheIn, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

FRIENDSGIVING

This is more of a friend event than a date but I figured I’d throw Friendsgiving into the mix just for fun. I will do a whole separate post on Thanksgiving outfits as it gets closer. A chunky sweater dress is the perfect piece to slip into. This one is the most amazing barn red and has a turtleneck which I love so much.

I added chunky black boots to give me some lift and to accessorize I popped on a black felt hat. This dress was rather shapeless so I added a black and gold ring belt to sinch the waist and pull the outfit together. This was definitely one of my favorite outfits of the post!

Outfit Details— dress: SheIn, shoes: SheIn, belt: SheIn, hat: Lulus, earrings: SheIn, watch: Fossil, bracelets: Mantra Band

HIKE 

Hiking to see the leaves changing colors is so popular in the fall. I, of course, would be doing it in style wearing the cutest faux leather Spanx set. I am a sucker for their stuff and this mesh sports bra is super fun. Pop on a little workout zip-up as temperatures cool down. Of course, I added my Apple watch to track those steps!

Outfit Details— sports bra: Spanx, leggings: Spanx, jacket: TJ Maxx, sneakers: New Balance, watch: Apple

WEDDING GUEST 

Fall is such a popular time for weddings and several of you said you could use some dress inspiration for your upcoming ones. I always recommend going for a midi dress. They are a bit dressier than something short and something silky like this one will leave you feeling oh so fancy.

However, you don’t want to look too dressed up so I recommend a shorter, slip-on mule rather than a tall heel. I love the way this pair looked with the midi-dress slit! I added a pair of butterfly earrings and a cuff to finish off the look. Other popular colors to wear this time of year are burnt orange, emerald green, (black of course!), and champagne.

Outfit Details— dress: SheIn, shoes: Lulus, earrings: Romwe, cuff: Mantra Band, necklace: The Silver Heron

CORN MAZE 

Corn mazes are oh so fun and something casual like this outfit will do just the trick. I’m starting off in a solid black tee. This one has shoulder pads which are so trendy right now! They look amazing tucked into wide-leg cropped pants.

This combo plays with shape and proportions which make it visually appealing. Keep things casual in a pair of simple black sneakers; these Supergas have been my go-tos lately.

Outfit Details— top: SheIn, pants: H&M, shoes: Superga, earrings: Romwe, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

FARMERS MARKET 

Farmer’s markets are always popping this time of year. Go for a sleeveless sweater; this is the perfect summer to fall transition piece and will leave you looking fall without overheating! I stuck with black jeans which quickly become a staple in my wardrobe this time of year.

These slip-on mules from Chinese Laundry are some of my most reached for in the fall. They have a baby heel to give me a little extra lift but are awesome for walking as well. They are so easy to dress up or down and are the perfect neutral color so they pair easily with just about anything!

Outfit Details— top: SheIn, jeans: Express, belt: SheIn, hat: Lulus, shoes: Chinese Laundry, earrings: Walmart, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

COFFEE 

A tee and jeans are all you need for a quick coffee date. This long sleeve is so soft and the twist-front detail is super unique. I can think of a dozen occasions this top would work for! I paired it with high rise straight leg jeans from Express. I wear these all the time and they are currently on sale; grab em while you can.

I’m adding a black purse and a simple pair of earrings to complete this look. With this outfit, you’ll look super cute without looking like you’ve tried too hard!

Outfit Details— top: SheIn, jeans: Express, shoes: Dingo, earrings: Walmart, bag: SheIn, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

FANCY RESTAURANT 

I am dying to wear this combo out somewhere because it’s just that good! I mean, who doesn’t love some snake print?! This print makes me feel so sassy and the silky material of this dress makes me feel oh so boujee. You could easily pair this dress with mules or over the knee boots but I wanted to dress it up.

So, of course, I slipped into lace-up heels. These are my new favorite pair and they make your legs look miles long. I added hoops and a black chain bag to elevate the look and boom instant 10/10 outfit.

Outfit Details— dress: SheIn, shoes: SheIn, bag: SheIn, earrings: SheIn, watch: Fossil, bracelets: Mantra Band

APPLE PICKING 

Apple picking seems to be on everyone’s mind these days. I love a simple sweater for this date; this one is so soft and the little tie-sides give it an extra something-something. I popped on a pair of cropped flare jeans and slipped into those same mules. To spice up my outfit, I’m throwing on a nude felt hat and butterfly earrings! How cute is this combo?!

Outfit Details— sweater: SheIn, jeans: Express, shoes: Chinese Laundry, hat: Lulus, earrings: SheIn, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

DRIVE-IN MOVIE 

Apparently drive-in movies are popular by you guys! We don’t have one near me but if we did, I would definitely be going. An oversized tee and leggings sound like the perfect outfit idea to me. This top is so soft and the slits along the sides make it the perfect length to wear with leggings.

This motto pair is from Spanx and will be on repeat all season long. They make it look like you put lots of thought into your outfit even if you got dressed five minutes before your date.

Outfit Details— top: SheIn, leggings: Spanx, shoes: Chinese Laundry, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron, earrings: SheIn

WINERY 

So many of you 21+ ladies said that you’re headed to a winery in the coming weeks so of course, I had to take care of you too! I obviously don’t know the typical dress code for this occasion but I figured you can never go wrong with a cute top and jeans.

This champagne top has the most amazing balloon sleeves and bustier-style cups which are so on-trend right now. I added heels to dress this outfit up and grabbed a nude purse to match. Booties or mules would also work with this outfit if you wanted a flat shoe option.

Outfit Details— top: SheIn, jeans: Express, shoes: SheIn, bag: SheIn, earrings: SheIn, watch: Fossil, bracelets: Mantra Band, necklace: The Silver Heron

ANNIVERSARY 

Many of you said you and your significant other are celebrating your anniversary soon so I’ve got you ladies covered too! This nude mesh dress is so cute. The polka dots are fun and flirty and there are a few ties that give this dress a unique shape.

I added black heels and matching black statement earrings to dress up the look. I assume anniversary means something a bit fancier than your typical date night, so I hope this outfit idea was in the ballpark, lol.

Outfit Details— dress: SheIn, shoes: SheIn, earrings: SheIn, necklace: The Silver Heron

FALL FESTIVAL 

This was hands down my favorite outfit of the bunch. I’m starting off in an adorable cropped top. I love the sleeves of this and because it’s on the shorter side, high waisted straight leg jeans were a must. I added mules and a buckle belt to slim the waist.

Every outfit seems better with a hat on so of course, my nude one from Lulus is having its moment. Gold hoops and a watch complete this look.

Outfit Details— top: SheIn, jeans: Express, shoes: Chinese Laundry, earrings: SheIn, belt: SheIn, hat: Lulus, necklace: The Silver Heron

FAMILY EVENT 

Family events seem to happen left and right around the holiday season! This sweater is perfect for whatever event you may be attending. The ruffled collar and bell sleeves make this sweater a bit dressier than your average one, however, pairing it with ripped skinny jeans will keep the look casual. I added white open-toed mules to match!

Outfit Details— sweater: SheIn, jeans: Express, shoes: SheIn, earrings: Walmart, necklace: The Silver Heron

DRINKS 

Drinks seem to be the most common first date for you guys! Flared jeans are my absolute secret weapon to confidence so naturally, I’d pull them out if I were in your shoes. These will make your legs look miles long and give your booty a nice lift.

They also look awesome with any crop top. This balloon-style one is so trendy right now and the nude pairs great with my heels. Throw on a chain bag for all of your going-out essentials.

Outfit Details— top: SheIn, jeans: Fashion Nova, shoes: Lulus, bag: SheIn, earrings: Walmart, necklace: The Silver Heron, cuff: Mantra Band

TAKE OUT + MOVIE

You don’t have to bum it when staying in! Getting dressed in a cute two-piece set will make you feel like your take-out and movie night on the couch is more exciting than it actually is. I love this burnt orange color and my Ugg slides are so cute and cozy with it.

Outfit Details— set: SheIn, shoes: Ugg

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

Because this post was so highly requested I will definitely do another one come winter. I cannot lie, I had a lot of fun putting together this post. Now if only someone would take me on one of these dates, lol! I hope you found this post helpful and that it gave you some outfit inspiration. Let me know what else you need help styling this season!

With love, McKenz

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Related Post: 16 Summer Date Outfit Ideas
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