6 Fall Outfits for Any Autumn Date this Season

Fashion
Written By Liv Birdsall

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Fall is the perfect season: the weather is comfortable, the colors of nature are bright and grounding, and comfort food comes back to the dinner table. I've always loved fall, though it feels short lived every year sandwiched between humid Labor Day and the eventual first snow (at least where I live).

However, fall is a time for exploring nature, getting cozy, and there tends to be some pretty perfect first date (or date night!) activities, too. From pumpkin patches to late-season baseball games, we’ve rounded up outfit inspiration for classic fall date nights so you don’t have to.

6 Outfits for Any Fall Date Night

When it comes down to it, fall outfits—date or not—are made with layered pieces in rich colors. There’s an emphasis on comfort and warmth, as well as being prepared for any weather… or maybe that’s a Midwest issue. Closet staples, like a solid color tee, jeans, crew necks, leggings, button-downs, and trousers can be combined into a fall outfit appropriate for any occasion. I like to add in earth tones—like wine red, olive green, and terracotta—to match the falling leaves outside. And fall is the time to dig out your cold-weather accessories, like beanies and scarves to keep warm.

Apple Picking

My first real date with my partner was apple picking and, since that date, we go back each year to pick Honeycrisp apples from a local orchard. It’s a great tradition; and it can be a fun date or group activity because the rows of trees span acres, leaving room for you to walk, chat, and try a bite of different apples along the way. When it comes to an appropriate fall outfit for the apple orchard, think on the casual side since you’ll be walking and weaving in and out of rows of trees. A cable knit sweater layered over a tank or bodysuit will keep you warm on windy days, and leggings will allow you to reach and climb for the prize apple if needed. If you go on a dry day, a pair of white sneakers will complete the fall date outfit with style.

A Bookstore or Cafe Date

A hot cup of coffee or hot chocolate tastes wonderful in the fall, especially on a chilly or blustery day. Bookstore and cafe dates are popular because you can talk more with your date, either wandering aisles of books and sharing your favorites or chatting for hours over a cup of something. For these dates, think dark academia vibes, rich colors, and polished fall outfits. A turtleneck and vest are top picks, especially paired with plaid or plain trousers. Finish the look with a trusty pair of loafers and a canvas tote to carry your things and the pile of novels you’re sure to pick up during the date!

A Pumpkin Patch

Another ideal fall date is an afternoon to a pumpkin patch, including cider donuts, and perhaps a corn maze or hay ride. For this fall date, you’ll want a versatile outfit that will keep you warm, but allow you to partake in all the activities the pumpkin farm has available. A long sleeve layered under linen overalls, both in earth tones and fall colors, are perfect to keep you warm without overheating. You can always layer on a jacket or sweater, too, like a shacket or trench coat. Keep your head warm with a chunky beanie, and your phone safe with this cute over-the-shoulder sling from Baggu. Most importantly, wear waterproof shoes (like Chelsea boots) because you’re sure to encounter dirt and mud at some point during the night. 

A Drive-In Movie

Who doesn’t love a drive-in movie? You get to watch a feature film—often Halloween classics during the autumn season—from the comfort of your own vehicle. Some people grab armfuls of blankets and make their car ultra cozy, some outfit the bed of a truck to make a lounge area, and some pack extra snacks and drinks to complete the date night. For this type of date, you’ll want a fall outfit that is comfortable since you’ll be seated most of the time. Try a pair of chino joggers (a step up from sweatpants) and a cropped crew neck for added warmth. Wear slip-on shoes so you can easily slide them off to tuck your feet under a blanket if it gets cold, and top the look with a denim jacket (ideally oversized) to still be comfortable over your layers. Finally, a pair of upcycled statement earrings will keep the focus on your face.

A Baseball Game

Going to a baseball game is a cute date idea during any season, but there’s a bit more of a magical feeling during the fall when the trees’ leaves start to fall and the season is nearing its end. You can wear any fall outfit to a baseball game, but we’re partial to a supporter’s tee shirt and jeans. Homage has the softest T-shirts—I promise you—for about every Major League Baseball team. Once you find a shirt, pair it with a baggy pair of jeans and classic Converse. You can even match the shoes to your team’s colors for added fun. Grab a plain Dad hat or a ball cap sporting your team’s logo if you have it, and wear a small fanny pack since most parks don’t allow large bags. 

A Night at Home

With the weather cooling off, at-home dates become more popular. Maybe you can have a game night, a movie night, or find a fall meal that you can cook together in the kitchen. I’ve always struggled with these date ideas myself because what kind of fall outfit do you wear, especially if you’re hosting? 

Instead of dressing up, I tend to stick to the basics—comfortable, layered Earth tones, in stretchy fabrics. A pair of flared pants and a zip-up in the same fall color creates a stylish monochrome outfit without stressing you out. Beyond those staples, you can play with different vintage T-shirts, slippers or house shoes, and your most comfortable undergarments. Whether you’re hosting or going to your date’s house, casual fall outfits will keep the night casual, too.

Fall dates are the best: you can explore the cool air, but get a hot drink to warm up afterwards. Plus, it’s basically the season for cuddling under a blanket to keep warm! Any fall outfit that makes you feel confident is a winner, but remember that autumn is a transitional season to wear layers whenever you can since temperatures can fluctuate dramatically over the course of a few hours. And when in doubt, a T-shirt, jeans, and a sweater won’t ever lead you astray. 

Liv Birdsall
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