Fashion

Fall Date Night Outfits That Are Classy And Fun

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Autumn presents the opportunity to be daring with outfits – thanks in part to layers, thicker fabrics and varying textures of the fall months.

This motto can be applied also to fall date nights. Gone are the breezy dresses of the summer, which now have been replaced by knee-high boots and a chunky sweater. 

The cooler weather presents a challenge to those who opt for a dress and heels. The key is to try and strike the right balance between sophistication and trendiness for the colder weather. 

Whether it’s a first date or a reoccurring date with your significant other, dressing up for a dinner date is an art. Throw in the extra variable of chilly fall weather and it can be a daunting task.

Fall Date Night Outfits

Strolling around a city, cocktails at a bar, or an upscale dinner.. each of these dates require a different outfit for the vibe.

Whether it is a first date or a reoccurring day of the month, dressing up for a date night is an art.

A little black dress is always a no-fail option, whether it be for the summer or winter months. Opt for a trench coat and knee boots to bring the dress into the fall season. 

Scroll below for fall date night outfits to give you inspo for your next date night.

Blazer + Dress + Boots

Instagram @lisadnyc

The key to a successful date-night ‘fit is striking the delicate balance between romance, comfort, and intrigue.

Nothing says perfect date night outfit quite like a black dress. There’s no more extraordinary style to default to than a little black dress.

But in particular, for the fall, pair it with a blazer or leather jacket for a fierce date night look. Regardless of personal style, it is the one item that is a must have item. 

Jacket + Top + Trousers + Boots

Instagram @le.petit.colette

Looking for a way to wear a sheer top in the fall? It’s the perfect way to layer and show some skin.

Use a leather piece (or two) to add some texture and dimension to the delicate top. Swap out black trousers for leather pants to add an edge.

This is the perfect fall date night outfit for a cocktail bar or coffee date. 

Jacket + Trousers + Flats

Instagram @_minesart

The beginning of fall can be tricky to navigate because as you’re transitioning from one season to the next, so is the weather.

On days when the weather fluctuates, layer a top with a statement jacket in autumnal hues to make the transitional weather a little bit easier.  

Choose luxe fabrics – think suede or leather to celebrate the cool weather. 

Blazer + Shorts + Flats

Instagram @vladislava.r

Shorts are not just reserved for the summer months.

Faux leather shorts are the perfect fall wardrobe piece. Not sure how to style them? When in doubt, head-to-toe black is always a winner.

Start with leather shorts and add in sheer knee high socks for a preppy take on the edgy shorts. 

Sweater + Skirt + Mary Janes

Instagram @symphonyofsilk

Autumn will forever be associated with classrooms, binders, and the academic aesthetic.

Even for a pleated skirt, there’s a grown-up fit for every personal style. There is even a modern take on the schoolgirl uniform for date night outfit ideas.

Add a cozy sweater to a skirt for a more casual date. 

Sweater + Skirt + Boots

Instagram @darya_burtseva


Up the ante on your date night attire by incorporating seasonal colors.

Chocolate brown, khaki and tan are an easy way to make up an autumnal outfit with little effort.

Experiment with different fabrics and textures in the same tonal palette for an easy date night outfit formula. 

Jacket + Skirt + Boots

Instagram @lolariostyle

Low-key elegance is easy to achieve by pairing a satin midi skirt and an autumnal jacket. Silk, satin, and suede are sexy options to create a layered look that are great for date nights.

Swap out a denim jacket for a rich suede jacket.

Finish off with tall boots or a pair of heels for a stunning fall date night look. 

Top + Skirt + Heels

Instagram @laurajadestone

A column skirt creates a cool silhouette that’s soft yet sleek. The classic staple is about to become a part of your wear-everywhere rotation for the fall. 

During those early autumn days, a simple top and a pair of pumps will be your date night look. 

Trench Coat + Jeans + Heels

Instagram @lglora

When the dress code requires you to look put-together, but is not quite cocktail attire, reach for jeans. Whether it be a low-key movie night or an exciting first date, denim is a no-fail option.

Jeans are the perfect one-and-done ensemble you can style up or down accordingly, and is a classic piece against the brisk weather.

Regardless of body shape, it is a great option for date nights. 

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