Fall Activities and What to Wear: 8 Ideas and the Outfits to Match

Written By Jen Crumrine

This post may contain affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through a link.

 

Every year I say I am going to do all the fall things, and every year I get to November having done about two of them. So this year I made the list first. Eight actual fall activities, from the orchard to a night on the couch, and the exact outfit I would wear to each one. Everything here is on Amazon, everything was in stock when I wrote this, and nothing costs more than about fifty dollars a piece. Pick one for this weekend.

 

My Top Picks at a Glance

  • Apple picking: Oversized batwing crewneck sweater, $27.99. Shop it here

  • The pumpkin patch: Oversized batwing sweater, $25.99. Shop it here

  • A fall picnic: Cable knit turtleneck sweater dress, $36.98. Shop it here

  • The farmers market: Chunky open-front cardigan, $19.98. Shop it here

  • A fall festival: Zip-up bomber jacket with pockets, $33.99. Shop it here

  • A coffee shop afternoon: Striped puff sleeve shorts set, $40.97. Shop it here

  • Pumpkin carving at home: Oversized ruffle hem boxy tee, $29.99. Shop it here

  • A Sunday reset: Two-piece long sleeve pajama set, $32.99. Shop it here

 
 

Apple Picking at the Orchard

An orchard is the one fall activity that punishes you for dressing up. You are reaching over your head, climbing a step ladder, and walking on ground that was mud two days ago. So this outfit is built around a sweater you can push the sleeves up on, real denim, and a sneaker with grip. The bag goes across your body so both hands stay free for the apples.

What to wear

  • Sweater: Oversized batwing crewneck sweater, $27.99. Shop it here

  • Jeans: High-waisted straight leg jeans, $32.99. Shop it here

  • Shoes: Suede retro sneakers with a gum sole, $27.99. Shop it here

  • Bag: Suede hobo bag with three straps, $49.99. Shop it here

  • Watch: Gold rectangle watch, $27.95. Shop it here

  • Earrings: Gold-filled double hoop earrings, $16.99. Shop it here

  • Necklace: Dainty layered gold chain stack, $13.29. Shop it here

What to bring

The basket is the thing that makes the photos, and it holds a real amount of fruit. The insulated mug is for the cider on the way home.

 

The Pumpkin Patch and a Hayride

I love a hayride and I have also learned the hard way that a heeled boot and a wagon full of hay do not get along. Comfortable shoes here, every time. The rest is the easiest fall formula there is: an oversized sweater, wide leg jeans, a belt so the proportions do not go shapeless, and a tote big enough for two small pumpkins and everybody else's water bottles.

What to wear

 

A Fall Picnic in the Park

A picnic is the one where a dress actually makes sense, because you are sitting down for two hours and nothing digs in. A cable knit sweater dress does all the work, the coatigan goes on when the sun drops behind the trees, and the flats are washable, which matters more in a park than anything else on this list.

What to wear

What to bring

The blanket is 80 inches square and waterproof on the underside, which is the part that matters when the grass is still damp at noon.

 

Saturday Morning at the Farmers Market

The market is short, cold at 8am, and warm by 10. So: a graphic tee under a big cardigan you can take off, jeans, a flat with a little color, and a tote you can actually load up. This is the outfit I wear most often in the fall, honestly.

What to wear

 
 

A Fall Festival

Festivals are a walking day disguised as a fun day. You will be on your feet for hours, so this one is built for that and then styled so it does not look like you are headed to the gym. A bomber over a fitted layer keeps the bulk down, and the bag is big enough for a jacket once the afternoon warms up.

What to wear

 

A Coffee Shop and Bookstore Afternoon

Not everything in fall has to be a whole production. For a coffee and a wander through the bookstore you want to look put together without trying, which is exactly what a matching set does for you. I am giving you two, because a coffee shop afternoon looks very different in Florida than it does in Michigan.

What to wear

  • Set for warm weather: Striped puff sleeve shorts set, $40.97. Shop it here

  • Set for cool weather: Zip-up sweat set with wide leg pants, $49.99. Shop it here

  • Shoes: Classic penny loafers, $44.99. Shop it here

  • Bag: Small suede shoulder bag, $31.99. Shop it here

  • Earrings: Twisted chunky gold hoops, $13.99. Shop it here

If you are somewhere still running warm in October, the shorts set is the one. If your mornings have turned, size up in the zip set and wear it with the loafers instead of a sneaker.

 

Pumpkin Carving and a Baking Day at Home

This is the messiest thing you will do all season, so nothing precious. An oversized tee with a ruffle hem is soft enough to sit cross-legged on the floor in and cute enough that you will not hide from the camera. Slippers on, because the whole point is that you are home.

What to wear

  • Top: Oversized ruffle hem boxy tee, $29.99. Shop it here

  • Leggings: High-waisted full length leggings, $6.99. Shop it here

  • Slippers: Suede platform house slippers, $43.99. Shop it here

What to bring

The carving kit is worth it. The serrated saws actually cut, which is the difference between a fun afternoon and a ruined pumpkin.

 

A Sunday Reset and Movie Night at Home

The end of it all. No agenda, no leaving the house. A real pajama set instead of leggings, a chunky cardigan to throw on when you get up for tea, slippers, and the small things that make an evening feel intentional rather than accidental.

What to wear

What to bring

These four are what turn a night on the couch into something that feels like a reset.

 
 

How to Dress for Fall Activities Without Overthinking It

Dress for a thirty degree swing, not for the forecast

A fall Saturday can start at 42 degrees and hit 70 by lunch. That is the whole problem with the season. The fix is one layer you genuinely want to take off, which means a cardigan, a coatigan or a bomber rather than a heavy coat, and something underneath you are happy to be seen in on its own.

Let the ground choose your shoes

Orchard, patch, festival: sneakers. Park and market: a flat. Coffee shop: whatever you want, this is your one chance to wear the cute shoe. I moved the tall boots out of every outdoor outfit on this list for exactly this reason, and I have never once regretted it.

Pick the bag before you pick the outfit

It sounds backwards and it works. If you need both hands, it has to be a crossbody. If you are hauling pumpkins or produce, it has to be a real tote. Decide that first and the rest of the outfit stops fighting you.

Buy pieces that work in more than one season

Almost everything on this list gets worn past fall. The jeans, the sweaters, the cardigan, the slippers and the sneakers all carry into winter. The only truly seasonal buys here are the carving kit and the candle, and those are under twenty-five dollars each.

 

Fall Activity Questions I Get Asked

What should I wear apple picking?

A sweater you can push the sleeves up on, jeans that are not white, and a sneaker with real grip. Add a crossbody bag so both hands are free. Orchards are muddier and colder than you expect, and you will be reaching over your head constantly, so skip anything cropped or fitted through the arms.

What do you wear to a pumpkin patch?

Wide leg jeans, an oversized sweater, a belt to keep the shape, and comfortable sneakers. Tall boots photograph beautifully and are genuinely miserable on a hay wagon. Bring a tote or a wagon for the small pumpkins.

Is it too cold for a dress in the fall?

Not with a sweater dress. A cable knit midi with a long cardigan over it is warmer than jeans and a tee, and it is one decision instead of three. Add tights if you are below about 55 degrees.

What should I wear to a fall festival?

Treat it like a walking day. Leggings or jeans, a fitted top, a light jacket you can tie around your waist, and the most cushioned sneaker you own. Bring a bag big enough to carry that jacket once the afternoon warms up.

What are some fall activities to do at home?

Carving pumpkins, a baking afternoon, and a proper Sunday reset with a movie. They cost almost nothing, they are the ones you will actually do on a rainy weekend, and they are the two I never manage to schedule and always enjoy most.

 

More Fall on the Blog

Fall outfits for women: a wardrobe refresh you will wear all season

The best fall decor on Amazon: cozy finds to warm up your home

Family Halloween costumes for every age

If you want these roundups before they go up on the blog, join the email list. I send the finds I am actually buying, a couple of times a month, and nothing else.

Jen Crumrine
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