What To Wear On A Fall Date – 4 Inspiring Outfits!

Our October lookbook is titled Harvest Moon, featuring beautiful layered looks with rich colors and textures perfect for an autumn evening. It got me thinking about special fall date nights and what dresses to wear on different occasions this season…for a nighttime haunted hayride followed by marshmallow roasting and storytelling around a fire, a fall feast among friends, or wherever else the evening may take you.

Above: Stay cozy while still looking put-together for a night outdoors full of haunted hayrides, hot apple cider, and marshmallow roasting around a bonfire. The Fairytale Crochet Maxi is a closet staple that can be worn so many ways – stunning on its own or an interesting piece when mixed with other items. Stay warm by layering the Stripe Boxy Embroidered Long Sleeve Tee on top and bundle up in the At Length Coat, Tapestry Scarf, Diamond Jacquard Buckle Headwrap, and Maven Tall Boot. Pile on the accessories with this look! Shown are the Cosmos Pendant, Comoros Moon Pendant, Timbuktu Studded Bangle, Cobra Bangle, Chain Braided Feather Bracelet. Keep your lips moisturized with some Mox Botanicals Lip Balm!

fall date what to wear

For a fall feast, dress for the occasion and the season in rich, autumnal colors. Don’t be afraid to pair the red Frances Bean Shift with the FP New Romantics Long Sweater Coat for a striking, festive combo! The Clipperton Fedora and Bansi Stilleto Bootie add to the sophistication of the look and keep accessories minimal – pictured are the Cosmos PendantSonic Portation Ring and Tapestry Embellished Cuff. We love the unexpectedness of pairing this outfit with the gorgeous Alameda Embellished Backpack.

fall date what to wear

Going to a concert?  Look casual and cool in the silky soft Duofold Lounge Dress, paired with a Distressed Bomber Jacket, Lee Boot and edgy accessories to toughen it up. Layer a bunch of bangles like the Tapestry Embellished Cuff, Timbuktu Studded Bangle, Cobra Bangle and Chain Braided Feather Bracelet. Store your wallet, phone, some deep red lipstick and any other essentials in the amazing Starry Sky Crossbody, paint your nails with Free People Polish in gold glitter and spice up your look by adding some color to your hair with Free People Hair Chalk!

fall date what to wear

Lastly, for a more casual evening of drinks at your local bar or stopping by a friend’s house party, we love pairing skinny denim or corduroy with heels for a more sophisticated take on a casual look. The new print in the Cord Skinny is amazing and looks perfect with the basic Keep Me Tee, Slouchy Sweater Jacket, and Selena Metal Toe Heel. Add some color with the India Tapestry Tote, some Free People Face Jewels and Free People Polish in Gun Metal, and a touch of intrigue with the Twigs Pendant.

Which look would you wear on a harvest moon date night?

Shop the October Lookbook.


  1. These outfits are great. I have a date to go on a few haunted hayrides this weekend with this guy I have liked for a really long time. What should I wear for that kind of date. I definitely don’t want to wear heals in case I need to run. Any advice would be greatly appreciated.

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