12 Best Fall Date Night Outfits September 2024

Fall is here, and that means it’s time to break out those cozy, cute, and flirty date night looks — perfect for both casual nights out and your next romantic getaway. Whether you’re getting ready for a first date or packing for a weekend trip with your partner, dressing up is always part of the fun. I’ve got a few trips lined up with my boyfriend, so I’ve curated some must-have, stylish pieces that you and I should both add to our carts ASAP.

Finding the perfect date night outfit can be tricky — you want to look chic but still comfortable enough to explore a new city or dine out. The key? A mix of romantic, timeless, and comfy pieces that are easy to pack and even easier to wear. From a satin slip skirt to black leather pants and suede booties, these fall style staples cover every date night idea from walking through a new city to a romantic dinner while on a fall trip. From now on, no more stressing over what to pack; I’ve rounded up the 12 best fashion items from Amazon, Madewell, and Nordstrom to make your next date night a stylish success.

Btfbm Women’s Satin Slip Skirt

A slip maxi skirt is a fall date night essential as it keeps your legs covered when the temperature drops but still feels feminine and flirty. Specifically, the Btfbm Satin Skirt is incredibly versatile, pairing beautifully with a fitted bodysuit and strappy heels or a flowy blouse and smart loafers.

PrettyGarden Women’s Fall 2-piece Sweater Set

This two-piece set is one you’ll want to reach for again and again; the sweater-like material fits the fall date night dress code by keeping you cozy while maintaining a chic, polished look. Plus, with 18 different colors to choose from, it ensures you’ll have plenty of options.

Tankaneo Women’s Long-sleeve Shirt

The Tankaneo Women’s Long-sleeve Top is endlessly versatile; it works for a casual date night by simply pairing it with jeans and boots, or you can dress it up with leather pants and heels for a more sophisticated look. One shopper raved that it’s “an incredibly flattering shirt” that will serve you well this autumn.

Free People Level Up Faux Leather Jeans

A pair of black leather pants is a timeless date night staple that effortlessly elevates any outfit without sacrificing comfort (you’d be surprised by how much stretch they offer). This Free People pair is currently 25 percent off at Nordstrom, which means you just found an affordable, high-quality addition to your capsule wardrobe for just $74.

Halife Women’s Long-sleeve Off-the-shoulder Top

The Halife Long-sleeve Top combines simplicity, elegance, and flirtiness thanks to its off-the-shoulder design. Pair it with jeans and black kitten heels for a relaxed vibe, or a mini skirt and high boots for something more daring. With close to 12,000 five-star ratings, it’s a clear winner in Amazon shoppers’ books.

Chigant Women’s Satin Blouse

The Chigant Women’s Blouse comes in handy when date night falls on a busy work day. Instead of running home to change, wear it to the office so your corporate look can seamlessly transition to what you’ve got planned for the rest of the night. Its understated, chic design pairs well with nearly anything, offering an effortless, put-together look. 

Cctoo Women’s Cold-shoulder Blouse 

If you’re ready to move away from neutrals, the Cctoo top is a great place to start. Its fun, fashionable design features open, cold-shoulder sleeves and elegant ruffled detailing, creating a flattering and playful silhouette that’s easy to style.

Madewell Melody Bubble-hem Midi Dress

We love a neutral fall dress, especially one that’s versatile enough to wear on casual nights or elevated with heels and jewelry for something more formal. Here, the bubble-hem design adds a fashionable and unique flair, and the dress is incredibly comfortable with pockets so you can enjoy your evening without worry.

Madewell Denim Western Maxi Skirt

A denim maxi skirt pairs seamlessly with high boots and a blouse or bodysuit for a date night or any occasion, especially if you have any fall trips on the horizon. The subtle Western-inspired detailing gives it an edge over other jean skirts, and the medium wash makes it a no-brainer for autumn.

Sam Edelman Michaela Mary Jane Flats

The Sam Edelman Mary Jane flats have quickly become my new favorite; I’ve been recommending them to friends and family because they’re not only chic and on-trend but they’re also incredibly comfortable. I can walk all over New York City without a blister in sight. The golden buckle adds a touch of sophistication, and if you’re skipping heels, these are the perfect alternative.

Anne Klein Rene Suede Boots

Every wardrobe needs a pair of black knee-high boots because they instantly elevate any outfit. The suede finish on these Anne Klein boots is a smart choice as it makes the pair ideal for fall and winter. Whether worn with a sweater dress, a midi skirt, or a blouse, these boots encourage a truly endless amount of styling options.

Sam Edelman Willette Kitten Heels

Kitten heels are making a comeback this season, and this Sam Edelman pair is a standout. The bow details and slingback design keep them feminine, while the sturdy block heel and supportive slingbacks ensure comfort. They’d look especially fetching with wide-leg jeans or looser trousers for a relaxed yet polished look.

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.