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

Dating is hard; deciding what the heck to wear shouldn't have to be. Picking out a dress, let alone what lipstick to pair with it, can feel more stressful than getting drinks with a stranger—I know from personal experience. Yes, styling outfits may be part of my day job, but I feel the same dread figuring out how to wear something that's date-y but not too over the top when I'm off the clock.

To solve my own problem (and yours too, of course), I decided to team up with one of Byrdie's beauty editors, fellow single lady Hallie Gould. Where I know a thing or two about dresses, Hallie's an expert in all things makeup. Together, we rounded up the dress-and-lipstick combos we find worthy of a first date, combos we're planning to test out ourselves the next time we have the occasion. If you're right there with us, read on—we've got you covered no matter where you're headed and, of course, whomever with.

Check out our ideal first-date dress-and-lipstick combos below!

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

Think drinks somewhere where the cosmos are surely overpriced.

& 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

The perfect balance of sweet and spicy. 

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)." — Hallie

Still 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

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