The Only Dress-and-Lipstick Combos You Need This Fall

Wilfred Lierre Dress ($125) + Estée Lauder All-Day Lipstick in Maple Sugar ($22)"The dress is casual enough for a low-key date, especially if you style it with sneakers and something simple like a leather jacket. Then, with a lip color that's similar but not too matchy-matchy, the look stands out." — Aemilia"I love this pick for a date—it's casual and comfy but still has that sexy, check out my curves factor. I decided to pair it with a similar brick-colored lipstick with brown undertones. It's creamy with medium coverage (i.e., it will fade nicely as you eat, sip, and possibly smooch)." —Hallie

Beaufille Forbes Modal-Neoprene Wrap Dress ($650) + Dior Addict Lip Glow in Pink ($33)"While it skews slightly fancy, this dress is just right for a more dressed-up date—think drinks somewhere where the cosmos are surely overpriced." — Aemilia"For a more grown-up, ladylike dress, I'd go for something sheer with a natural finish. Dior's Lip Glow keeps your lips looking dewy (not glossy) with just a hint of pink. Double points because you won't have to touch up throughout the night." — Hallie

& Other Stories Slit Slip Dress ($125) + MAC Lipstick in Media ($17)"I'm all about the slip dress right now. It's a little boudoir without feeling overly showy. I love that Hallie picked a deep lip to pair it with because it makes a statement without taking away from the dress." — Aemilia"Go full-on '90s with a slip dress and moody lipstick to match. It adds a grunge-soaked edge your date will undoubtedly be into and will make you feel seductive all night." — Hallie

H&M Crushed Velvet Dress ($50) + Dolce & Gabbana Dolce Matte Lipstick in Dolce Flirt ($38)"If you're dressing to impress, this is the style you need. The velvet is lush, which makes me think of a lipstick that's rich and luxe, too." — Aemilia"A slinky little number calls for the LBD of lipsticks—the true red. It shows your confident, powerful, and can pull it all off no matter the setting. Apply a matte liner underneath for added staying power and precision." — Hallie

Mango Pleated Dress ($100) + RMS Beauty Lip2Cheek in Beloved ($36)"When you're a girl who's all for having fun on a first date, this dress is playful and pretty. A strappy pair of black heels will dress it up while you can swap for flats if you're just grabbing coffee." — Aemilia"When you've chosen something short and swingy, I love adding a messy, slightly melted pop of color. RMS's Lip2Cheek is perfection—just dab it on with your finger to get that popsicle-stained effect." — Hallie

Reformation Prue Dress ($218) + Charlotte Tilbury Hot Lips in Kim KW ($32)"Since off-the-shoulder tends to feel a little flirty, pairing with a nude lip is the perfect move. With the addition of a cute (but comfy) pair of heels, you'll feel dressed up but not fussy." — Aemilia"Sometimes, less is more. In this case, let your décolletage and bare shoulders do all the talking and apply a classic nude. Developed specifically for Kim Kardashian West herself, Charlotte Tilbury's Hot Lips offering is a barely there option that won't only score you a second date, but rather help you break the internet." — Hallie

Rouje Janet Robe ($147) + Honest Beauty Truly Kissable Lip Crayon in Mulberry Kiss ($18)"For some reason, wrap dresses always have a distinctly French feeling to me. Styled simply with a hint of lip color, it's exactly the je ne sais quois that makes Parisian girls stand out." — Aemilia"This cute mini wrap dress looks prim but showcases a lot of leg, the perfect balance of sweet and spicy. Accessorize the look with this light wash of color that is neither matte nor glossy, but somewhere dream-like in between." — Hallie

Saloni Grace Off the Shoulder Midi Dress ($625) + Buxom Big & Sexy Bold Gel Lipstick in Vampy Plum ($22)"I can imagine wearing this dress to a moody yet tropical spot (is that a thing?) or somewhere with music that allows for a little dancing to end the night. Add a bold bag, tuck your lipstick inside, and you're good to go." — Aemilia"Atop a dress that feels like a fall harvest wonderland, try a dark plum to match. It'll bring out the pretty reds and purples in the dress as well as keep you on theme for the season (and who doesn't love a theme?)." — Hallie

Staud The Pablo Dress ($125) + L'Oréal Paris Colour Riche Collection Exclusive Red Lipcolor in Zoe's Red ($6)"Chalk it up to the retro vibes of this colorful mini, but a funky lip seems like just the thing to finish off this look." — Aemilia"Dark red and burnt mustard is perhaps my favorite cold-weather combo. Pairing the two on a first date will show you're not afraid to be bold." — Hallie

Topshop Reclaim Ruched Slip Dress ($85) + Anastasia Beverly Hills Liquid Lipstick in Dusty Rose ($20)"As previously mentioned, I'm fairly sure you can't go wrong with a slip dress. If you're looking for a little more coverage (since it is a first date, after all), consider layering a fitted tee underneath." — Aemilia"I'm into whites with soft, romantic hues like mauve and dusty rose. Apply this liquid lipstick for a velvety texture with a ton of super-pigmented color payoff." — Hallie

Zara Jacquard Mini Dress ($100) + Nars Lipstick in Heat Wave ($28)"This dress catches my eye because while it's decidedly fancy, it's easy to dress down with the right accessories. For a date, the length is a little flirty, but you still have coverage so you won't feel over-exposed." — Aemilia"Coordinate your lips with your dress for that extra wow factor. For this, I'd slick on Nars's bright, orangey red matte (which also happens to be one of my all-time favorite lipsticks)." — HallieStill on the hunt for what you want to wear for your big date? See the night-out looks New York girls always wear!Opening Image: Collage Vintage