It's Cuffing Season! 9 Date-Night Outfit Ideas That Will Come in Handy

It's officially that time of year! Love it or hate it, there's something about a new season that acts as the not-so-soft launch of cuffing season. It can inspire you to put yourself back out there or, at the very least, re-download a few dating apps. However, the harsh realities of dating can dash some of that initial romanticism. Finding someone special can feel harder than finding vintage Gucci by Tom Ford. And when you do find that elusive someone? Setting up date-night plans can seem like you're running in the season finale of Survivor because you're never really sure you'll cross the finish line.

Even once you've overcome all those initial hurdles, there's another challenge to overcome: choosing what to wear for a date night. You spend hours sifting through clothes trying to figure out an outfit—but selecting one for a date? Well, that's even more dreadful. After all, who doesn't want to put their best self forward for the special occasion? Thankfully, there's a simple solution. Keep scrolling. In an effort to make the process a little less stressful, we've scoured social media in search of styling inspiration for every type of date—be it a night at the theater, a movie night, a trip to an art gallery, or anything else.

Ahead, we're sharing nine date-night outfit ideas with easy-to-copy formulas, styling tips, and shopping recommendations. No matter how long you've been seeing someone, these simple, sophisticated, and sultry ensembles are sure to impress.

WHAT: Getting Drinks

WEAR: Lace Camisole Top + Earrings + Wide-Leg Trousers + Pumps + Shoulder Bag + Chunky Cuff Bracelets

Styling Notes: When you've got plans to meet them for drinks right after work, it's hard to know what to wear—until now. You can make your trusted wide-leg trousers transform from day to night by styling them with a lace camisole top, chunky cuff bracelets, and pointed pumps. It's a formula that's approved for happy hour.

WHAT: Gallery Opening (or Museum Date)

WEAR: Earrings + Turtleneck + Tweed Jacket + Miniskirt + Tights + Slingback Flats + Handbag

Styling Notes: If your date-night plans include something fancier—such as a trip to a local museum or an art gallery opening—don't be afraid to wear a more "formal" outfit. Pair a tweed jacket with a turtleneck, miniskirt, tights, and slingback flats for a sophisticated yet simple outfit.

WHAT: Movie Night

WEAR: Trench Coat + T-Shirt + Belt + Jeans + Ankle Boots + Hobo Bag

Styling Notes: Planning on seeing the newest blockbuster film for your date night? Don't underestimate the importance of choosing an outfit that makes you feel comfortable (and chic) throughout your movie night. You can make your coziest T-shirt and relaxed jeans dressier for movie night by styling them with a trench coat, statement belt, hobo bag, and ankle boots.

WHAT: Casual Dinner

WEAR: Earrings + Corset Top + Baggy Jeans + Pointed Heels + Mini Bag

Styling Notes: Finally, they've texted you! But with an impromptu date on the books, the question remains: What do you wear for a casual dinner? Start by opting for a sultry corset top, which is a surefire way to keep your significant other's attention from across the restaurant table. You can keep the rest of the look simple by styling it with baggy jeans, pointed heels, statement earrings, and a mini bag.

WHAT: Fancy Dinner Date

WEAR: Oversize Gray Blazer + Gray Slip Dress + Red Strappy Sandals + Red Handbag + Red Lipstick

Styling Notes: If you've managed to snag a reservation at one of the best restaurants in town, you want to make the occasion extra special. But if you're stressed about what to wear for a formal dinner date, look no further than the outfit formula above. When in doubt, throwing on a little lipstick with a slip dress, oversize blazer, strappy sandals, and a small handbag will always be a safe bet.

WHAT: Attending a Concert

WEAR: Oversize Hoops + Halter Top + Low-Rise Pants + Heels + '90s Shoulder Bag

Styling Notes: You've been gifted the best surprise: tickets to your favorite musician in concert. But what do you wear? No matter what type of concert you're going to for date night—be rap, pop, or country—you can't go wrong with creating a look that gives "video vixen" energy. Opt for a halter top styled with low-rise pants, hoop earrings, heels, and a '90s shoulder bag.

WHAT: Dancing Night

WEAR: Long Leather Trench + Red Minidress + Sheer Tights + Strappy Sandals + Mini Bag

Styling Notes: Planning on hitting the dance floor with your partner for your next date night? Put on something that will make you feel like a dancing queen (in your own right); more specifically, opt for a red minidress and a comfortable pair of heels. You can always make your look more appropriate for cold weather by adding a long leather trench coat and thermal tights.

WHAT: Live Music (Jazz or Opera)

WEAR: Oversize Earrings + Bodycon Maxi Dress + Chunky Cuff Bracelet + Heels + Clutch Bag

Styling Notes: Not spending the evening on the dance floor? If your next date night includes live music but no disco ball, take it as an opportunity to dress to the nines. When in doubt, you can't go wrong with wearing a bodycon maxi dress styled with statement jewelry, heels, and a clutch bag.

WHAT: Night at the Ballet (or Theater)

WEAR: Faux-Fur Coat + Pearls + Black Dress + Sheer Tights + Pointed Mules + Leather Gloves + Clutch Bag

Styling Notes: Nothing is quite as special as a date night spent at the ballet or theater, so it calls for an outfit that suits the occasion. But by no means do you need to wear a gown; in fact, you can get away with wearing a classic black cocktail dress. Just dress it up a bit by styling it with pearls, tights, mules, and a faux-fur coat (or lighter jacket).