15 Cute Date Outfit Ideas for Fall

Celebrity stylist Tiffany Briseno is taking the guess work out of what to wear by sharing some suggestions that are sure to wow.

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Cute Date Outfits That Will Make You Excited for Fall Style
Photo: Getty Images/InStyle

Summer doesn't technically end until Wednesday, September 22, but every autumn lover knows that while the calendar might say otherwise, the season actually comes to a screeching halt when all things pumpkin and spooky start popping up in stores. Seeing as how Bath & Body Works already dropped its Halloween collection, we think now is as good a time as any to start preparing for all things cozy — including fall date night outfits.

If COVID continues to stay under control and more people get vaccinated, we're willing to bet your social calendar for fall is going to be packed. To make sure you're ready for anything and everything, begin by making seasonal swaps to your wardrobe (look to these celebs for inspo), then start to brainstorm some cute fall outfits ideas you can wear out with your significant other, or even while getting together with friends.

Granted, this might be easier said and done, considering last fall was mostly spent indoors decked out in loungewear, baggy sweats, and a lot of tie-dye. But have no fear: We reached out to stylist to the stars (see: Shawn Mendez and Cathrine O'Hara) Tiffany Briseno for some serious inspiration.

Apple or Pumpkin Picking

date night
Melodie Jeng/Getty Images

The most quintessential fall dates call for equally quintessential fall outfits. Ergo, Briseno recommends pairing your favorite oversized cable knit sweater with a pair of ripped jeans and accessorizing with a large brim hat, combat boots, wool socks. As far as color scheme, Briseno favors a cream palette, but whatever makes you feel and look your best is perfect.

Shop now: Everlane The Oversized Stroopwafel Turtleneck in ReCashmere; $168

Shop now: Madewell The Perfect Vintage Jean in Rosabelle Wash; $135

An Afternoon at a Winery

date night
Hanna Lassen/Getty Images

According to Briseno, sipping wine on a brisk fall afternoon calls for an A-line cotton dress patterned with some kind of large, jewel-toned print. Then, top things off with a leather moto-style jacket and Cuban heeled booties.

Shop now: Express Cropped Vegan Leather Moto Jacket; $148

Shop now: All Saints Lenora Leather Boots; $349

Picnicking in the Park

date night

The early weeks of autumn when the weather is still warm are perfect for picnicking in the park. Dress accordingly in 1940s-style high-waisted shorts, an oxford shirt tied at the waist, and espadrilles, says Briseno, adding that accessories should include a basket textured bag and headscarf.

Shop now: Athleta Midtown Shirt; $98

Shop now: 8 Other Reasons Seize the Day Black Multi Floral Print Hair Scarf Set; $48

Touring a Haunted House

date night

Getting spooked calls for all the comforting clothes. Briseno recommends opting for classic style sweatpants, a matching cropped crew neck sweatshirt, and Air Max 97's to ensure that even if you're not cool, calm, and collected, your outfit will be.

Shop now: Nike Air Max 97; $170

Shop now: Champion Classic Reverse Weave Sweatpant; $50

Going on a Hay Ride

date night
Claudio Lavenia/Getty Image

Keep things simple on a hayride through the pumpkin patch with a white collared shirt and overalls, Briseno says. Then, finish off the look with a pair of rubber Chelsea boots.

Shop now: BLANKNYC Indigo Straight Denim Overalls; $128

Shop now: Dr. Martens 2976 Quad Platform Chelsea Boot; $180

Cozying Up by a Bonfire

date night
Christian Vierig/Getty Images

Want to be cozy but still look cute for this autumnal date? "A linen dress, crochet poncho, and flat sandals" are Briseno's go-to for nights socializing around the bonfire.

Shop now: Mango Textured Fringed Poncho; $100

Shop now: Mayra Slide Sandal; $70

Shopping at a Farmer's Market

date night
Edward Berthelot/Getty Images

Strolling through your local farmer's market makes for the perfect Sunday morning date. Briseno tells InStyle to swap your grocery store look for a pair of flared, high-waisted trousers and a cropped vintage tee tucked in for the occasion. Accessorize with an eco-friendly tote bag and white Air Force 1s to complete the ensemble.

Shop now: Fashion Union High Waist Kick Flare Tailored Pants Set; $48

Shop now: Nike Air Force 1 '07; $90

Grabbing Coffee

date night
Edward Berthelot/Getty Images

Grabbing coffee is a classic date idea for fall, winter, and beyond, but to dress for the occasion in autumn, Briseno would gravitate towards "a crop knitted tank top, flounce skirt, denim jacket, leather loafers, and mini backpack purse."

Shop now: Zara Cropped Knit Top; $18

Shop now: Reformation Flounce Skirt; $98

Going on a Hike

date night
Christian Vierig/Getty Images

Getting active calls for, you guessed it, athletic wear — with flare, of course. According to Briseno, the fit for this fall date is "a pair of biker shorts with a matching sports bra, an oversized button-up shirt worn open, hiking boots, and a bucket hat."

Shop now: H&M Cotton Bucket Hat; $13

Shop now: Bandier High Tide Bra & Soleil Biker Short Kit; $150

Brewery Hopping

date night
Christian Vierig/Getty Images

When asked to style the perfect bar or brewery-hopping ensemble, this is how Briseno broke it down: Victorian sleeve wrap blouse, high waisted mom style jeans, and Cuban heel strappy sandals. We'll cheers to that.

Shop now: ADAY That's A Wrap Top; $145

Shop now: Stradivarius Ultimate Authentic Mom Jean in Mid Blue; $50

Netflix and Chilling

date night
Jeremy Moeller/Getty Images

For those cool autumn nights that are perfect for a movie marathon (scary flicks or otherwise), Briseno says to keep things casual-cute with flared knitted pants and a neutral-tone, matching cardigan set.

Shop now: Pixie Market Ivory Knit Bolero and Tank Set; $129

Shop now: Express High Waisted Stretch Knit Flare Pant; $80

Attending a Football Game

date night
Edward Berthelot/Getty Images

If you're not committed to a team or don't own a jersey, Briseno says a pair of boyfriend jeans, a vintage knitted polo shirt, and bright colorway sneakers combo is always a winning fit for a football game.

Shop now: AE Highest Waist Ripped '90s Boyfriend Jean; $60

Shop now: Victor Glemaud Polo Vest Top; $165

Outdoor Dinner

Date Night

While it's still comfortable to eat outside, Briseno recommends taking advantage of the weather and donning a fitted sheer printed dress with slip-on sandals and a mini shoulder bag to dine outdoors. And if your reservations are for later on in the evening, bring a leather 80's style blazer, just in case.

Shop now: Mansur Gavriel Pencil Case Leather Bag; $495

Shop now: Rejina Pyo Cameron Topstitched Faux Patent-Leather Jacket; $795

Drinks at a Rooftop Bar

date night
Christian Vierig/Getty Images

Skipping dinner and going straight to the drinks? If you're hitting up a rooftop bar, Briseno says an '80s style vest worn as a top with matching straight leg trousers is the perfect outfit. And if you really want to make a statement, she adds, strap on a pair of colored pumps, and add contrast with a printed purse.

Shop now: Abercrombie Linen-Blend Vest Set Top; $45

Shop now: Schutz Lou Pointed Toe Pump Women; $98

Bike Riding

date night
Jeremy Moeller/Getty Images

Last but not least, if you're hitting the road on a romantic bike ride through your neighborhood or a local park, Briseno says to pass on your usual biker shorts ensemble and opt for a flirty floral wrap dress with an A-line skirt, white sneakers, and a silk scarf headband to complete the look.

Shop now: En Saison Floral Print Faux Wrap Long Sleeve Dress; 98

Shop now: Keds Women's Champion Originals; $50

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