50+ Stylish Fall Date Night Outfits (2024) - Lorna Ryan (2024)

I have rounded up 50+ ideas for fall date night outfits. Whether you are looking for a very cute fall date night outfit, a casual fall date outfit, or a fancy, fall dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

I included lots of classic fall date night outfit ideas like a leather jacket, little black dress, and knit dresses (one of my favs!). I’ll keep this blog post updated with perfect fall date night outfits. Pin so you can come back to this blog post for fall outfit inspiration. There are already beautiful pieces in stores for this fall season and I am excited for what is to come!

Some of the below fall date outfits will be perfect for a casual fall date, such as a coffee date or apple picking. Other outfits will be perfect if you are looking for fancy fall date night outfits for a special occasion or an exciting first date.

Whatever your personal style this fall, know that there are no hard and fast rules when it comes to dressing for fall date nights. The most important thing is that you feel comfortable and enjoy yourself. Incorporate your personal style and have fun dressing this fall.

Fall Date Night Outfits:

Without further ado, here are some of my favorite pieces you can mix and match for the perfect fall date night outfits. Hope you get lots of inspo from these cute fall outfits for date night.

Fall Date night outfit idea: Leather Jacket

One of the perfect date night outfit pieces is a quality leather jacket or moto jacket. A leather jacket is so versatile and a statement piece for your wardrobe, whether for a date night outfit or day-to-day outfits.

Adding a leather jacket with a little black dress or some skinny jeans makes easy date outfits. Leather jackets work for casual date outfits, dinner date outfits, and most date night adventures. I’ve rounded up some cute leather jacket and moto jacket options below.

Fall Date night outfit idea: Little Black Dress

One of my favorite fall date night outfit ideas is a little black dress. Little black dresses never go out of style and are one of the best investment pieces for fancy date night outfits.

It’s really easy to personalize a little black dress by mixing and matching it with some cute accessories below (see some of my favorite picks at the end of this blog post!)

The best thing about an elegant little black dress is that you can wear it for a special occasion to a nice dinner date or you can tone it down by pairing it with a leather jacket or a moto jacket.

With little effort, you can completely change the look of a little black dress with different accessories. Find your perfect fall date night dress below that will also be perfect for the holidays. I love buying pieces that will work year-round.

Fall Date night outfit idea: Date Night Dresses

Along with little black dresses, other cute dresses make the perfect date night outfits. I love dresses for fall date nights as they are one piece, which makes the whole outfit.

They are really elegant and simple to accessorize for a complete look. There are so many pretty dresses out right now for fall date nights. I have picked a few of my favorites. I love the fall colors!

Fall Date night outfit idea: Skinny Jeans

Skinny jeans are another key item to have in your wardrobe. There are so many styles, colors and finishes of skinny jeans that you can have as staple investments.

A classic pair of skinny black jeans or a darker wash are great options for fall date night outfits. Having a classic (and comfortable) pair of skinny jeans that suit your personal style is a great way to mix and match with cute tops for date night.

There are so many cute fall date night outfits with jeans once you have the perfect pair of skinny jeans. Here are some of my favorite styles that feel great on.

Fall Date night outfit idea: Off the Shoulder Top

Off-the-shoulder tops paired with skinny jeans are very cute fall outfits for date night. Off-the-shoulder tops come in the prettiest colors for fall. In the cooler months, it’s an easy way to show a little skin without freezing! This can turn a more casual date night look into a fancier date night outfit.

Off-the-shoulder tops come in various shapes and styles so you can find the perfect one for your body shape. Crop tops are really in right now. While they look very cute, they are not my style. As I mentioned above, the most important thing about your fall date night outfit is that you feel comfortable and confident in your outfit. We all have different ideas of what a cute outfit for a fall date night means so pick and choose what suits you best.

Here are some pretty off-the-shoulder tops that I love right now.

Fall Date night outfit idea: Oversized Blazer

Oversized blazers make another great date outfit for fall, especially in the cooler months. Oversized blazers can be dressed up or down for fall date-night outfits or dinner date outfits.

One of my favorite things about oversized blazers is that you can really incorporate your personal style with blazers. They can be elegant and chic or more chic and grunge.

Here are some cute oversized blazers that you can use to elevate your date night outfits.

Fall Date night outfit idea: Shirt Dress

Another one of my favorite casual fall date outfits is a shirt dress paired with a moto jacket.

Date night outfits do not need to be overly complex or stressful. A shirt dress is the perfect option for a casual date or a casual outing.

Shirt dresses are also great in cooler weather as you can pair them with a trench coat and some leather leggings. In warmer months, you can always drop the leather leggings if the shirt dress is long enough. One of the best things about shirt dresses is that they are cute outfits for date night but make the perfect staple pieces for your fall wardrobe. Another easy fall date night outfit idea.

Fall Date night outfit idea: Leather Pants

Leather pants have been all the rage over the past couple of years. Leather pants are the perfect alternative to skinny jeans. Having a good pair of leather pants is a staple in your wardrobe, especially during fall.

Leather pants over a shirt dress are the perfect fall date night outfit for a happy hour. Spanx has a particularly great variety of comfy leather pants. Spanx is known for being super comfy and fashionable.

Fall Date night outfit idea: Midi Skirt

A midi skirt is a great casual fall date outfit paired with white sneakers or cute comfy shoes if you are planning on a date of walking or exploring. A midi skirt is easy to dress up or dress down.

If you are unsure on the dress code, then a midi skirt with flats is always a good option. During the fall months, midi skirts are the perfect date outfit, with a plain white t-shirt or a graphic t-shirt.

Fall Date night outfit idea: Boho dresses and Maxi Dress

Maxi dresses can still come out for fall date nights. I love maxi dresses for spring and summer and still wear them in Fall. They make the perfect date outfits and are an easy way to incorporate some cute and comfy dresses into your fall capsule wardrobe.

I pull out the same maxi dresses year after year for a fancy look that is also very comfortable. Win-win! While these dresses may be a little much for a casual first date, they are perfect for an evening dinner while watching the sunset or the perfect outfit to take on vacation. These dresses last year and after year, which saves me needing lots of new outfits.

Maxi dresses are definitely a classy date night outfit and the perfect elegant date night dresses to wow.

See all my favorite Salty Crush dresses here.

Fall Date night outfit idea: Denim Jacket

Get the last few wears out of your summer denim jacket in the fall. If you are planning on wearing a maxi dress for your fall date outfit, then the perfect match is a pretty denim jacket.

Denim jackets are wardrobe staples that are perfect for fall date nights. Denim jackets go with everything from maxi dresses to midi skirts. I have a few denim jackets and have had them for years. Here are some options that make the perfect chic fall date outfit.

Fall Date night outfit idea: Long Coat

Living in San Francisco has taught me the importance of a beautiful long coat. Having a few good long coats in your wardrobe will be the perfect investment for fall date nights that will carry you into winter.

Long coats can be an outfit in themselves if you are going to be outdoors on your date. Long coats are the perfect accompaniment to the little black dress, midi skirt, or skinny jeans mentioned above. These coats make the perfect date night outfit, especially for fall date night outfits.

There are so many long beautiful coats available to suit all body types. Some of my favorite retailers for classic long coats are River Island, Karen Millen, Ann Taylor and Express. They always have classic coats with pretty details that make the coats memorable.

Fall Date night outfit idea: Trench Coat

For a perfect fall date night outfit, a trench coat is a great alternative to a long coat, which may be too heavy for fall depending on where you are living. A trench coat is another great option for a casual fall outfit or an elegant fall date night outfit.

Ann Taylor, Karen Millen, Express and River Island all do really pretty trench coats. Trench coats are always an effortless look that look really chic and put together.

Fall Date night outfit idea: Knit Dress and Sweater Dresses

For fall date night outfits, knit dresses, and sweater dresses are great options. They can be perfect for casual date night outfits or a dinner date outfit depending on the fit and style. Sweater dresses are classic fall pieces and great capsule pieces that will last you through the season.

How you accessorize knit dresses is key for dates. Adding a cute gold chain belt, pretty headband or statement necklace can make all the difference. See lots of my favorite accessory picks below.

Using accessories to add touches of your personal style is a great way to lift the outfit and bring sweater dresses to life. You don’t always need a new outfit for every date. You can change up looks by mixing and matching accessories. With a little effort, sweater dresses can look fun.

Here are some pretty knit dresses and sweater dresses for the perfect date outfit.

Fall Date night outfit idea: Knee Boots

I have picked out some cute knee boots that are great options for fall date outfits. These knee boots would make the perfect date night outfit when paired with jeans or a cute dress such as a shirt dress or sweater dress.

Fall Date night outfit idea: Comfortable shoes

I think 2020 & 2021 taught us the luxury of being comfy! I found Birdies shoes in 2019 and am now in love with the brand. They are like slippers, but very pretty slippers that you can wear around the house or on dates.

Birdies has shoes that are perfect for work, dates, fancy nights out or for lounging around the house. I have picked out some fun options for pairing with skinny jeans for a casual date outfit. I have also picked cute ones for a dinner date outfit. Birdies are such comfortable shoes that I highly recommend.

Read my full Birdies Review and see all of my favorites here.

Fall Date night outfit idea: Pair of Heels

I still love a pair of (comfortable) heels so I can dress up for a special date night. I love Sarah Flint heels as they are so comfortable and last ages. You can read my full Sarah Flint review here. My Sarah Flint code SARAHFLINT-CCLORNA1 gets 15% off your first pair of Sarah Flint shoes.

Sarah Flint shoes are expensive but they are truly worth it! I have 4 pairs and love them all so much.

Fall Date night outfit idea: Hairband

It’s time to talk about some fun accessories for your stylish fall outfits. I love accessorizing. It fills me with so much joy. There is nothing like a good headband to add instant glam.

I have picked out some beautiful headbands that can be worn to glam up a casual fall date night outfit or add the finishing touches to a fancy fall date night outfit. Date outfits are your time to get creative and use all your extra sparkly items! Headbands are an easy way to turn a cute date night outfit with jeans into a fun statement.

Fall Date night outfit idea: Pretty bag

I love dainty, pretty bags and bring them out at the weekend for date nights. During the week, I appear to need the kitchen sink in my bag so I always tend to have a bigger bag with me. These are some pretty fall date night purses for carrying all of your important things while adding a touch of glam.

If you are interested in the prettiest floral handbags for spring and summer, see my full round up here.

Fall Date night outfit idea: Jewelry

I have included lots of simple accessories below for adding some glam to your fall wardrobe.

Your casual fall date night outfit can get a twist of glam with a dainty gold necklace, some studs or even a statement necklace. There are so many accessories that you can use to give you easy fall date night outfit ideas that suit your personal style.

Accessories and jewelry are a great way to mix things up and create new looks from what you already have in your wardrobe.

Here are some cute jewelry pieces to upgrade your date night looks.

Hope you enjoyed browsing through my top ideas for fall date night outfits. As I mentioned above, I’ll keep this blog post updated for lots of new options for fall date night outfits. Pin this blog post so you can come back at any time to get some new ideas for cute outfits for fall.

Whether you are leaning towards a little black dress or a leather jacket and jeans for your perfect date night outfit, you will look equally fabulous. Enjoy your date night!

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