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Date night is more than quality time with your boo — it’s an excuse to dress to the nines and make the dining room your runway. Take a page from the books of Taylor Swift or Blake Lively and up your date night fashion game with our editor-curated outfit ideas for fall. This season, the new ladies who lunch are the divas who dine.
Whether you’re stepping out for a first date, a romantic anniversary, or well-deserved drinks on a Friday night, it always pays to feel polished. Self-love is of utmost importance after all, and there’s nothing more powerful than the natural allure of a someone who’s clearly feeling themself. However, dressing sexy in the fall is a careful dance. The temps have dropped, which means you’ll need to be strategic with the skin you show and select stylish layers to keep you warm. Comfort is still key, regardless of the occasion. Pro tip: Start with outerwear, like a puffer jacket, leather jacket, or trench coat, and an elegant designer handbag with shiny hardware. (Our pick of the season? The coveted Coach Tabby Bag.)
After that, the outfit writes itself. Select items that play into the palette of those staples (we’re loving merlot red and chocolate hues that are trending for fall), add ankle boots or sleek slingback pumps, and then incorporate finishing touches like chunky earrings, an intoxicating perfume, and, of course, your trusty lipstick or lip gloss. Don’t afraid to pull out your most luxurious fashion pieces and beauty products, too. Date night always qualifies as a special occasion — even if you’re just grabbing a slice of pizza.
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After you book that reservation, grab inspiration for fall date night outfits below, and keep scrolling for WWD Shop editors’ night out essentials to stash in your bag.
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Sleek & Chic
When in doubt, paint it black. Not only is it supremely easy to match with other pieces, but the hue is always flattering and simply sexy. Canada Goose’s plush and sumptuous Elie Blanket Coat hacks the classic puffer jacket silhouette with shapely waist cinching, a soft shawl collar, and a removable pocket pouch for your keys, lip balm, or wallet (though, ideally, you won’t need to have cash on hand). We layered the look with the Skims Soft Lounge Long Sleeve Dress because it serves as a blank canvas for other accessories, along with providing reliable warmth and snatching support for your curves. Then, break up the blackout palette with pops of bold gold, whether with the Coach Tabby Shoulder Bag 26, statement shoes, or chunky earrings.
Coach Tabby Shoulder Bag 26
Canada Goose Elie Blanket Coat
Skims Soft Lounge Long Sleeve Dress
Shown with: A New Day Women’s Jaz Ball Heel Stretch Ankle Boots with Memory Foam Insole ($44.99), Alexis Bittar Gold Crumpled Drop Earrings ($275), Quince Open Contour Cuff Bracelet ($99.90), Glossier You Rêve Eau de Parfum ($78)
Dark Romance
This one’s for the lover girls. Date night is the perfect excuse to pull out your most romantic items and pretend you’re in a rom-com. The first order of business? Red lipstick. Nothing screams “main character energy” like leaving behind your lip print on a wine glass, dinner napkin, or the cheek of someone special. We’re partial to this luxurious Prada lipstick that pairs beautifully with a red designer handbag. A silky slip dress, draping wool top coat, and pearl earrings allow the overall look to feel soft and feminine, while a knee-high boot with an easy kitten heel will keep you comfortable and chic through the city streets.
Reformation x Kacey Musgraves Stella Lace Trim Silk Midi Dress
Staud Ollie Leather Shoulder Bag
Max Mara Agata Wool Belted Top Coat
Shown with: Everlane The Banana Boots ($350), Ana Luisa Maxine Pearl Drop Earrings ($58.50), Prada Beauty Monochrome Hyper Matte Refillable Lipstick ($50)
Leather & Legs
This look is inspired by Swift’s daring date night ensembles that often incorporate short hems to highlight her long legs. The outfit formula is a great way to repurpose items from the summer, too, be it corset top or a silky halter blouse. Opt for a wool-blend mini skirt like this one from Cos for added warmth, then layer with sheer black tights for a bit more coverage. An oversized leather jacket will help insulate the heat without sacrificing on edgy attitude — match it with a slouchy bag and a sexy pump that elongates your legs, and you’re off to the races.
Wilfred Martini Satin Blouse
Cos Brooch-Detail Wool-Blend Mini Skirt
Banana Republic Vegan Leather Moto Jacket
Quince Italian Leather Handwoven Mini Hobo Bag
Shown with: Larroudé x Altuzarra Pumps in Black Patent Leather ($490), J.Crew Swiss-Dot Tights ($22.50), Quince Silver Threader Drop Earrings ($49.90), Maison Margiela Replica On a Date Eau de Toilette ($165)
Shop More Fall Date Night Essentials
Coach Tabby Shoulder Bag 20
Tom Ford Santal Blush Eau de Parfum Fragrance
Price upon publish date of this article: $195
Coach Card Case
Price upon publish date of this article: $95
Fenty Beauty Gloss Bomb Stix High-Shine Gloss Stick
Price upon publish date of this article: $25
Chanel La Crème Main
Price upon publish date of this article: $62
Rare Beauty True to Myself Tinted Pressed Talc-Free Finishing Powder
Price upon publish date of this article: $30
Touchland Salted Caramel Power Mist Hydrating Hand Sanitizer
Price upon publish date of this article: $10
Glossier You Rêve Eau de Parfum
Price upon publish date of this article: $78
Prada Beauty Monochrome Hyper Matte Refillable Lipstick
Price upon publish date of this article: $50
Maison Margiela Replica On a Date Eau de Toilette
Price upon publish date of this article: $165
Charlotte Tilbury Mini Glossy Pink Lip Gloss + Liner Set
Price upon publish date of this article: $25
Urban Decay Mini All Nighter Waterproof Makeup Setting Spray
Price upon publish date of this article: $17
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Meet the Author
Olivia Cigliano is a Commerce Writer & Producer at Footwear News and WWD where she writes and edits shopping content across fashion, beauty, footwear, TikTok style trends, and more. Cigliano received her bachelor’s degree in journalism from Emerson College, and her byline can be found in publications including Elite Daily and CR Fashion Book. She is currently based in New York City. Cigliano regularly reports on seasonal fashion trends and new fashion releases at WWD.
