10 First-Date Outfits to Win His Heart This Fall

Make a stylish first impression on your first date, starting from head-to-toe.

Couple Riding Bikes
(Image credit: Marie Claire)

Despite the quickly dropping temperatures, your love life has no choice but to continue on through the fast-approaching chilly season. For your struggles to stay warm and look first-date-ready, we bring you 10 outfits you need to try this fall to make a stylish first impression that starts from head-to-toe.

#1: The modern take on a flirty, classic style.

Woman in Red Dress

(Image credit: Karl-Edwin Guerre)

#2: A simple sweater and jean combo made not-so-simple with thigh high boots — the perfect finishing touch for any first-date locale.

Woman in Jeans, Cardigan & Boots

(Image credit: Karl-Edwin Guerre)

#3: A cozy ensemble with a leather-legged edge. This sweet look will satisfy your date's eye candy cravings.

Woman in Yellow Jumper & Yellow Leggings

(Image credit: Karl-Edwin Guerre)

#4: It's "sexy," "girly," and "tough" all bundled up in one sweet package: you. Say "hello" as you step into his car, feet first, in your own strappy heels.

Woman in Dress with Leather Jacket & Strappy Heels

(Image credit: Karl-Edwin Guerre)

#5: Pro-tip: Include an attention-grabbing pop of color that'll make an unforgettable first impression.

Woman in Brown Jacket, Orange Skirt & Orange Heels

(Image credit: Karl-Edwin Guerre)

#6: It's a prep school graduation that's totally chic and both season- and date-appropriate.

Woman in Preppy Outfit with Long Black Coat & Boots

(Image credit: Karl-Edwin Guerre)

#7: Minimalism done the right (and sexy!) way.

Woman in Black & White Outfit

(Image credit: Karl-Edwin Guerre)

#8: A pretty ensemble for everything from the coffee shop to the romantic dinner.

Woman in Blue Dress & Long White Coat

(Image credit: Karl-Edwin Guerre)

#9: An eclectic, multi-printed get-up that flaunts a timeless, '60s inspired skirt.

Woman in White Spotty Skirt & Leather Jacket

(Image credit: Karl-Edwin Guerre)

#10: A look that screams "feminine" and will make your date the first of many.

Woman in Winter Outfit with Purple Scarf & Purple Bucket Hat

(Image credit: Karl-Edwin Guerre)

Which of these will you be wearing on your next first date? Tell us in the comments, below.