#Street Style

12 Foolproof Fall Date Night Outfits

by Emily Tozer

12 Foolproof Fall Date Night Outfits

Picking date night outfits can be tough whether it’s your first date or your 50th. The perfect outfit is flattering and comfortable, plus it shows off your personal style. To cut down on outfit changes, polling your friends, and last-minute shopping sprees, we have 12 perfect date night outfits for this fall.


Black + White



A simple shift dress with a leather jacket will never go out of style. Classic date night outfits like this one on Crystalin Marie are always good to have in your back pocket for a last-minute invitation to a concert or a happy hour. Choose a dress in your favorite color so you’ll feel most confident.





An off-the-shoulder top with long sleeves is the perfect piece if you still want to show a little skin in the chilly fall weather. Pair it with sleek, skinny jeans and heels as Annabelle of Viva Luxury did for a happy hour date.


Little Black Dress



You can’t go wrong with a LBD for a day-to-night date or if you’ve been kept in the dark about plans. We love the crocheted details on Ro’s of The Bloggerella. Switch up your accessories to make it work for anything from a dinner date to an evening spent gallery hopping.


Lace Dress



Getting dolled up in a fancy date night outfit is almost as much fun as going on the date itself. Next time you want to get glam for your guy, pull out a showstopping dress like this red lace number on Christine of Hello Fashion.


Flared Jeans



You may not want to go full-on ’70s for your first date, but a flattering pair of flared jeans will still make a statement. Keep your silhouette in focus by teaming them with a simple silk top and pointed-toe shoes like Sheryl’s of Walk in Wonderland.


Leather Skirt



We love fall date night outfits that are cozy and feminine. Lauren of This + That got it right with her soft sweater and leather skirt. The best part of this look is the versatility—add tights or swap in heels depending on where your date is taking you.





Emily of The Sweetest Thing has mastered the perfect formula for cozy fall date night outfits: a chunky cardigan, a silk cami, and skinny jeans. Mirror her look if you and your guy are heading to an apple orchard or a scary movie.


Floral Dress



We love date night outfits that look effortlessly feminine. A flirty floral dress will always be a cute choice. Dark floral prints in burgundy or navy like Sheridan’s of Blue Eyed Finch are perfect for fall.


Jump Suit



If you and your guy have been dating for a while and you’re running low on new date night outfits, try switching out pieces like your go-to LBD for a sexy jump suit. We love how Nany’s Klozet finished her look with layered necklaces and a pop-of-color bag.


Mini Dress + Trench Coat



Layering for chilly fall weather doesn’t mean you can’t show off your figure with flirty date night outfits. Opt for a simple bodycon mini dress, and keep it elegant as Stephanie Sterjovski did with a drapey trench, pointed pumps, and a chic updo.


Lace + Leather



When it gets too cold to slip on a mini dress, try a date night outfit like this pairing of a lace top and leather pants. Just as with this one on Aimee of Song of Style, the look is the right balance of sweet and sexy.


Fringed Skirt



Putting together a casual date night outfit isn’t always as easy as slipping on a LBD. Marisela of Diverse City Style strikes a balance between stylish and comfortable with a slouchy button-up shirt and a flirty fringed skirt—an easy formula to re-create no matter what your personal style may be.