11 Fall Date Outfits To Help You Stand Out

A woman trying on a sweater and looking at herself in the mirror
The fall season can be the perfect time for going out with your date. The days can still be warm, but the crisp, fresh air is a welcoming change from those humid, summer days. Although it can get chilly, fall date activities can make wardrobe planning somewhat challenging.  So how do you choose your fall date night outfit? We have the top 11 perfect fall date night outfit ideas for you to make your selection easier. When it comes to fall date night, be sure to keep in mind some of these fun wardrobe choices.
  • Have fun with flannel
  • Sweater weather
  • Bring on the boots 
  • Layer up for comfort
  • Texturize with corduroy, leather, or suede 
When your clothes make you feel confident and comfortable, you may be less anxious when meeting someone new. Just because it’s chilly, that doesn’t mean your style has to suffer!

The traditional jeans and a t-shirt combo with a stylish jacket

Woman standing against a brick wall wearing jeans and a t-shirt and a stylish jacket
Donning a pair of jeans and a t-shirt does not have to be the lack-luster outfit many believe it is. Partnering your favorite designer jeans with a t-shirt is still a stylish way to dress up for a date.  Add a touch of personality by getting creative with your tops. This versatility is a terrific way to bring color and flourish to your outfit. When you pair it with a jean jacket or a stylish blazer you can remain comfortable on those cooler fall days.

A classy pantsuit

Break out a classy pantsuit as the perfect choice for a fall outfit ready for romance. You can find ones with wide legs, high-waists and oversized suit jackets to fit any occasion.  Pantsuits are flexible enough to wear with a formal or casual top to alter how you want to appear on your date. 

Tight turtleneck and skirt

Woman dressed in a tight black turtleneck and a printed skirt

A tight turtleneck is a terrific piece to pair with your favorite skirt. A wide range of patterns and textures in materials will emulate class and comfort while out on a date. Turtlenecks provide a sophisticated look while covering up for those chilly fall evenings.

This top is not only for pants anymore. Tight turtlenecks pair well with a suede or leather skirt for any occasion.

Remember to drink responsibly. You want to have a ride home, and you do not want to drink too much that you feel sick and have to cut your fun evening short. Also, it can be hard to track your glasses when you are having a good time. So try to include a glass of water in between each alcoholic drink. This way, you stay hydrated and will be able to have a whole night of fun!

Long sleeve blouse, printed vest and pants

When the season changes, your perfect fall date night outfit can be a simple combination. A long sleeve shirt and an attractive vest with your favorite pair of pants is an easy ensemble. Depending on which seasonal activities for couples you both enjoy, it works well for any date. 

Opt for a vest with patterns or designs to add flair to your fall outfit. Not only will you be cozy while out on a date, but you will also catch his eye.

Maxi dress and blazer

Woman wearing a maxi dress
Maxi dresses are not only for those warm spring or summer months. Stretch out the time you can enjoy this wardrobe item by adding a complimentary blazer. This combination is a stylish way to be comfortable while enjoying many date ideas.

Pencil skirt, long sleeve blouse and knee-high boots

Fall in love with pencil skirts again, as one of the best ways to remain classy and feminine throughout the year. The length of these skirts is perfect for windy, cooler days since they remain in place. Combine it with a fashionable long sleeve blouse and knee-high boots for the best look.

Colorful blouse with an ankle-length skirt

Woman looking at her phone, dressed in a brightly coloured blouse and white skirt
The fall season doesn’t mean you need to ditch those bright-colored items in your closet. Wear those dazzling blouses for a cheerful wardrobe choice to contrast fall colors. Pair a vibrant blouse with an ankle-length skirt to show personality in your style.

Long sleeve bodysuit, skinny jeans and boots

A stylish and trendy fall outfit can be your skinny jeans with a long sleeve bodysuit and designer boots. Bodysuits are flattering and help end the need for you to adjust your top when standing from sitting.  Every closet should have at least one bodysuit that will go with a nice pair of jeans. They come in many colors and styles while giving you a comfortable and stylish top. Perfect for an easy date night out to dinner and a movie.

Cocktail dress and leather jacket

Woman wearing a printed cocktail dress and leather jacket

You don’t have to sacrifice style and femininity because the weather is cooler. Many date ideas will need a more formal wardrobe choice. These situations call for a cocktail dress paired with a classy leather jacket.

There is no need to pack away these cute items so soon when fall comes. Add an attractive leather jacket to keep warm and extend your cocktail dress season.

A flannel shirt with jeans or khakis and tan boots

It wouldn’t be the fall season if you didn’t see some flannel at some point. The growing popularity of this material expands way beyond the red checkered shirt. It can give your fall outfit a trendy sense of style and comfort. 

Throw a colored flannel top over your t-shirt to accent your jeans for a relaxing day out. Or button it up for another option that is ideal with a pair of khakis. Don’t forget to include some tan-colored boots to round out this perfect fall date night outfit.

Cozy sweater and corduroy

Woman sitting on the floor wearing a cozy sweater

The dipping temperatures call for a comfy but stylish sweater. They are comfortable and versatile enough to pair with corduroy pants or a skirt. For anyone who likes to avoid form-fitting clothing, sweaters are ideal. They can provide an attractive wardrobe piece to ensure you remain confident out on a date.

With dozens of sweater choices, you are sure to find an attractive item to suit your style and taste. Corduroy is a terrific material to go with this top during the cooler fall months. It gives you a fashionable way to stay warm and cozy.

The takeaway

Choosing an outfit for a date in the fall doesn’t have to be hard! We hope you like the sound of one (or more!) of these outfits so that you can stay confident and comfortable when you’re getting to know your date!
Cheryl Wozny

Cheryl Wozny

Cheryl is a wife, mother of four, and a published author who has dabbled in many different niches for over a decade of writing. Her focus on honest and genuine connections helps provide practical information that anyone can use, regardless of their current relationship status.

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