10 Fall Date-Night Outfits That Are All Hits, No Misses

So your text conversations are hitting the right note, and it's time to finally meet up. Or maybe you're due for a break from dinners on the couch and have an exciting night out planned. Whether it's a first date or a reoccurring slot on your calendar, dressing up for a dinner date is an art. Throw in the extra variable of chilly fall weather and it's like tackling a scientific formula. How do you show skin without freezing by the end of the night or make a statement in high heels without collecting a fresh set of blisters? Luckily, the below outfits will help you do just that.

The key to a successful date-night 'fit is striking the delicate balance between romance, comfort, and intrigue. Whether you're going on a movie date or are in for a Michelin-star evening, these looks are useful jumping-off points to formulate your own date-night uniform. All are A+ options, so keep scrolling to see them all as well as the pieces to shop for. Here's to a road of successful fall nights ahead.

Maxi Skirt + Tube Top


(Image credit: @jullie.jeine)

Style Tip: A tube shirt and column skirt create a cool silhouette that's soft yet sleek.

Black Tube Top + Black Textured Pants


(Image credit: @fongminliao)

Style Tip: When in doubt, head-to-toe black is always a winner. Start with leather pants and add in a simple black strapless top.

Vibrant Cutout Dress + Bright Sandals


(Image credit: @deborabrosa)

Style Tip: Vibrant colors are heavy wardrobe lifters without much effort. A color this saturated is bound to get all of the attention.

Sequin Halter Top + Tailored Shorts + Sheer Stockings


(Image credit: @annelauremais)

Style Tip: As the chilly weather sets in, repurpose your tailored shorts with the addition of stockings. 

Long-Sleeve Knit Sweater + Voluminous Skirt


(Image credit: @hannamw)

Style Tip: Low-key elegance is easy to achieve by pairing a voluminous A-line skirt and a fitted knit top.

Poplin Shirt + Straight-Leg Jeans + Heels


(Image credit: @sasha.mei)

Style Tip: When your dress code requires you to look put-together but is not quite cocktail attire, try jeans with a crisp button-down and flashy heels.

Tall Boots + Minidress + Long Coat


(Image credit: @cassdimicco)

Style Tip: The bright spot about cooler weather? The coats. A statement coat and heeled boots are really all you need to wow your date come October.

Oversize Blazer + Cropped Top + Slip Skirt


(Image credit: @endlesslyloveclub)

Style Tip: A boxy blazer with a fluid satin skirt create an interesting contrast that's sophisticated yet modern.

Ruffle Top + Jeans + Heeled Boots


(Image credit: @alllisonho)

Style Tip: Take note of the current '90s wave and pair your ruffled top with easy straight jeans. For casual drinks or a late-night walk, this combo isn't too buttoned up. 

Sheer Dress + Long Coat


(Image credit: @shhtephs)

Style Tip: If you're down for the risqué side of things, embrace the open-knit trend with a cool dress meant to catch eyes. To leave a little to the imagination, layer a leather coat over it.

Fashion Market Editor

Indya Brown is a fashion editor, stylist, and writer living in Los Angeles. While going to school at Columbia University in New York City, she got her feet wet in the fashion industry interning at Elle magazine, Harper's Bazaar, and New York magazine's The Cut. After graduating in 2016, she joined The Cut as a fashion assistant, eventually working her way up to fashion editor. There, she worked on a multitude of projects, including styling inbook feature stories for New York magazine's print issue, writing and pitching market stories for The Cut, and serving as fashion lead for The Cut's branded content. While New York has been her home for over 10 years, she moved to Los Angeles in the midst of the pandemic in 2020 for a new chapter. Now she is a fashion market editor for Who What Wear, focusing on emerging designers, rising trends on and off the internet, interior design, and BIPOC creatives and brands. Aside from her duties as a fashion market editor, Brown is also a freelance stylist and writer, working on national print and video commercial campaigns for Sephora, The Independent, and Cadillac. Her bylines also include Harper's Bazaar, Vox, and The New York Times. But once the computer goes down and the emails turn off, she's likely eating her way through Koreatown, hunting down vintage furniture, scoping out new outrageous nail designs to try, or taking a hot cycling class.