Don’t let a change in the temps stop you from channeling major confidence this fall with a lineup of flawless first date outfits. (Sure, it may take a little more layering and some strategic styling on your end, but it can be done.) Between tailgates at your alma mater, haunted hayrides and a visit to your local apple orchard (or pumpkin patch!), you’re going to need a slew of dependable going-out options on standby — ’cause wearing the same slip dress and bomber jacket will inevitably get old after a while. In place of carefree summer rompers and off-the-shoulder dresses, you’ll find solace in these 22 next-level date-night essentials that will give your prized LBD a run for its money. Pssst: You can *totally* rock pants or a jumpsuit when hanging with your boo.
1. Scotch & Soda Pleated Skirt ($125): Achieve a ‘70s-meets-geek-chic look with this emerald green pleated skirt that’s begging to be teamed with a retro striped sweater. Proceed to step up your style game with some leopard print ankle booties and throwback hoop earrings for a Taco Tuesday outing with your better half.
2. Reformation Cosmos Jumpsuit ($248): When it comes to playing the dating game, you’re in it to win it. Make a lasting first impression with this red haute wrap jumpsuit, complete with a deep-v neckline and criss-cross back, that’s worthy of the final rose. Pair it with a sleek bomber jacket and going-out platforms for a bombshell look.
3. Zara Printed Top ($30): What’s that you say? Too cold to venture out in just a handkerchief crop top? Girl, puh-lease. Take style cues from the Man Repeller herself by layering this bow-adorned top over a lightweight turtleneck for double the warmth and panache. Top off your look with a vampy red lip and high ponytail for a night on the town.
4. 7 for All Mankind Mid-Rise Ankle Skinny Cords ($199): Obsessed would be an understatement. It’s never too early to break out the cords, especially when they’re this downright witchy. The autumnal floral print is not only a shoo-in for Halloween, but it’s date night-approved when teamed with a lace-up blouse and sparkly skimmers.
5. Loeffler Randall Nicolette High Heel Sandal ($450): Introducing the black heeled sandals with a playful pouf that can be spotted at least a mile away. These man-repelling ankle-tie steppers are guaranteed to be a hit when styled with cropped denim flares and a next-level button-down featuring extra-wide sleeves.
6. ASOS Satin Top With Cold Shoulder & Ruffle Sleeve ($55): Covering up doesn’t have to mean blasé. Case in point: This chartreuse cold-shoulder blouse, featuring fluttery sleeves and ruffles, will elevate any pair of black slacks or boardroom culottes with minimal effort. Just toss on a statement necklace and some lace-up ghillies for a candlelit dinner at your favorite restaurant.
7. J.Crew Collection Leather Leggings ($495): A trusty pair of wear-everywhere leather leggings (yes, leggings!) is the wardrobe workhorse you’ll reach for time and time again this season. Major bonus: These come in a deep red wine color that’s perfect for fall. Style ‘em for a post-work date alongside a tomboy-chic button-down and d’Orsay flats, or channel an off-duty look with a luxe knit sweater and a French-girl top knot.
8. Tobi The Morgan Color Block Maxi Dress ($68): For the overly modest, this burnt orange maxi dress is not. Between fall weddings in the idyllic countryside and an early Halloween bash (just toss on a witch’s hat to complete the look), you won’t run out of excuses to whip out this seasonal staple. Come date night, don’t hesitate to take it there with an of-the-moment suede choker bolo necklace and a cool fedora.
9. Nasty Gal Crochet Call Mini Dress ($88): When your LBD grows stale, you need a goldenrod dress that evokes the changing leaves and fall harvest. This embroidered crochet number can be styled with a denim jacket for a low-key date at the farmers’ market or a picnic under the stars. Wear it with dramatic gladiators now and riding boots once the temps dip low.
10. French Connection Bloomsbury Garden Pleated Maxi Skirt ($128): Cue the romance with this autumnal floral pleated maxi skirt that has us lusting after a chunky mock-neck sweater and suede ankle booties. Our favorite part? Obviously the come-hither thigh slit that allows you to show off some serious leg. Your date will definitely feel inclined to lend you their jacket when the air gets nippy during a hayride at dusk.
11. Zara Dress With Sequinned Collar ($26): Yes, you can wear white after Labor Day weekend — here’s proof. In lieu of your summer whites, opt for an off-white that plays well with rich fabrics and deep autumnal hues. This sequined collar dress — which requires zero styling, BTW — is a no-brainer for a dinner banquet or an evening at the ballet. All that’s missing is a hands-free cross-body bag and some chunky block heels for a show-stopping look that doubles for a.m. and p.m.
12. & Other Stories Kaleidoscopic Glitter Sneaker ($145): Turn down for what? It’s ‘bout time you updated your sneaker collection with a pair of these Lady Gaga-esque sparkly kicks that show off your adventurous side. Pair them with an entrance-making LBD for a black-tie affair, or go full-on athleisure with a leather mini and bomber jacket for a night at the club.
13. Wilfred Dalida Blouse ($145): Don’t back down now — this ultra-femme black lace blouse demands attention. We can’t explain it, but there’s just something about black lace that exudes instant sex appeal. Dial up the drama with some dazzling statement earrings for a fancy dinner party, or better yet, when meeting your S.O.’s ‘rents for the first time.
14. & Other Stories Faux Leather Culottes ($95): When in doubt, remember that leather always reads fierce. These after hours-approved culottes can be teamed with a billowy blouse and pointy toe pumps for a DDG look that will make people stare. For an #OOTN (outfit of the night) that’s worthy of a first date (think: grabbing drinks and hitting the dance floor afterwards), keep it casual with a white tee and a retro varsity jacket.
15. Topshop Tall Metallic Pyjama Shirt ($90): The key to looking put together without trying too hard is to do less. For an I-just-woke-up-like-this look that packs a punch, you need a slinky pajama blouse in your life STAT. This metallic shirt not only sports a relaxed fit, but it looks ah-maz-ing with mom jeans and sky-high steppers. *Adds to cart.*
16. Babaton Malik Blouse ($85): Your beloved off-the-shoulder blouse from summer just received a major upgrade — and with tie accents at the sleeves, no less. For a coffee date followed by a romantic stroll through the park (PSLs in hand, of course), a versatile striped shirt with this much around-the-clock appeal will always do you right. Style it with leather pants and slip-on sneakers, or channel your inner girl next door with a herringbone blazer and a denim button-front skirt. Your move.
17. Zara Oriental Print Bodysuit ($40): YAS, girl. A don’t-mess-around bodysuit with a rocker ‘tude is more than deserving of a spot in your date-night lineup. This oriental blouse featuring a deep tie-up neckline leaves just the right amount to the imagination, especially when styled alongside embroidered jeans and tough-girl Chelsea boots. Count us in, please.
18. Nasty Gal Running Wraps Plunging Dress ($78): If we can’t stop staring, then we know your date won’t be able to either. This blush-colored wrap dress featuring a plunging neckline has anniversary dinner (or fall soiree) written all over it. Edge it up with a ‘90s-inspired choker and a leather moto jacket for a getup that slays into the early hours of the morning.
19. Tularosa Shea Dress ($148): When a borrowed-from-the-boys flannel shirt dress reads too casual, take it up a notch with this pristine bow-neck dress that’s equal parts classy and fabulous. Wear it to the office with power pumps and a blazer before transitioning your look for cocktail hour with some chunky-heeled loafers and chandelier earrings.
20. Zara Short Tapestry Skirt ($40): If your idea of sexy for fall involves nubby knit sweaters, A-line minis and pointy-toe boots, then you’re obviously doing something right. Feast your eyes upon this floral tapestry skirt that’s made for gals who like to play by their own rules. With a trusty parka and riding boots on standby, you’ll easily be equipped for an afternoon at the pumpkin patch.
21. Nasty Gal Matisse Graffiti Leather Boot ($198): After trying these bad boys on for size, a pair of plain ol’ black leather ankle boots simply won’t do. Reach street MVP status like that sporting these scene-stealing floral graffiti print stompers that are guaranteed to elevate even your most basic t-shirt dress or scandalous summer slip dress. For max perfection, a fringed knit cardigan and cropped flares will have you ready to take on every fall function in your iCal.
22. Kimchi Blue Vanessa Velvet Fit + Flare Romper ($69): We’re crushing hard over this berry-hued velvet romper that can be styled one of two ways. Enjoy the late-summer to early-fall transitional weather while you still can by paring it down with your fave vintage denim jacket and Chuck Taylors. Once it’s time to bundle up, a long-sleeved t-shirt, fishnet tights and combat boots will keep you toasty enough to trek out for Oktoberfest with your main squeeze.
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