I Asked a Stylist to Curate My Fall Activity Outfits — Shop Her Picks, Including an On-Sale Suede Barn Jacket

Cute for pictures, practical for the farm

Stylist-Approved Fall Macy’s Pieces

• Pumpkin Picking-Approved (and 44% Off!): And Now This Short-Corduroy-Stand-Collar Bomber Jacket, $50 (orig. $90)
• For Your Apple Orchard Photo Op: Tommy Hilfiger Ponte Knit Band Collar Jacket, $104 (orig. $149)
• Celeb-Worn Brand: Levi’s Cinch-Waist Lightweight Baggy Jeans, $54 (orig. $85)
• Rich Fall Colors: Good American Oversized Rugby Collared Sweater, $139 (orig. $198) 
• Trendy Animal Print: Sam Edelman Michaela Mary Jane Flats, $160

I look forward to autumn all year, so the chill in the air fills my stomach with butterflies — and my mind with fall activity outfit ideas. Since autumn is my favorite season, I’m already filling my calendar with pumpkin carving, trips to apple orchards, spooky hayrides, and nights at the fair.

Instead of spending hours searching Pinterest for inspo, I asked fashion stylist Molly West Coe to curate my looks for every activity on my fall bucket list. She scoured Macy’s for cozy sweaters, leg-elongating jeans, and sleek sneakers that won’t be ruined by a traipse through the pumpkin patch. Many of her picks are on sale with the promo code BEST.

Related: Michelle Monaghan’s Tailored Fall Look Is from My Go-To Brand for Sleek Outfits — and Her Exact Pieces Start at $45

1. For the Pumpkin Patch

While I always want to snap a sweet photo while pumpkin picking with my nieces and nephews, I don’t want to wear something that looks fashionable but feels so stiff that I can’t fully participate. That’s why Coe recommends a pair of Levi’s baggy jeans, a brand that celebs wear, and a fuss-free rugby shirt. “With this, you’re keeping it cute and efficient without being worried if it gets messy,” Coe shared. For a refined touch, she suggested matching the burgundy top with a bag and sneakers in the same color.

Good American Oversized Rugby Collared Sweater $198 $139 at Macy’s	Levi’s Cinch-Waist Lightweight Baggy Jeans $85 $54 at Macy’s
New Balance 327 Sneakers from Finish Line $105 at Macy’s	Lauren Ralph Lauren Suede Small Blaike Barrel Bag $275 at Macy’s

2. Apple Picking Uniform

Though apple picking doesn’t require as much squatting and bending as the pumpkin patch, I still want an outfit that allows me to move easily — and won’t be ruined by potentially soggy grounds. For this, Coe pointed me to a pair of ankle-length jeans and Mary Jane flats that won’t sink into muddy terrain. With its bright red color, this structured jacket will draw in the colors of the orchard, making sure I look cute but stay comfy.

Tommy Hilfiger Ponte Knit Band Collar Jacket $149 $104 at Macy’s	Kenneth Cole Pleated V-Neck Top $89 $62 at Macy’s
Sam Edelman Michaela Mary Jane Flats $160 at Macy’s	Good American Vintage Straight Ankle Jeans $158 at Macy’s

Shop More Stylist-Approved Fall Flats 

Puma Speedcat Cow Print Ballet Shoes $100 $56 at Macy’s	Steve Madden Eleve Square Toe Ballet Flats $99 $69 at Macy’s
DV Dolce Vita Karma Woven Slip-On Flats $69 $41 at Macy’s	Franco Sarto Tesia Square Toe Ballerina Ballet Flats $130 $77 at Macy’s

3. Hayride Must-Haves

I have a confession: I am the friend who, when told to dress casual, shows up in a dress and heels. So when Coe showed me this trendy plaid dress paired with this now 44 percent off corduroy jacket, I was sold. “For a hayride, you’re sitting and not doing a ton of walking,” shared Coe. If you dress this up you can easily grab dinner afterward, too, she says. Plus, I can’t wait to snag these rich, chocolate-brown suede boots she selected to mix and match with my other pieces. 

And Now This Short-Corduroy-Stand-Collar Bomber Jacket $90 $50 at Macy’s	Sanctuary Autumn Edit Plaid Sleeveless Midi Dress $159 at Macy’s
Sam Edelman Harmony Zipper Short Booties $170 at Macy’s	Coach Pillow Brooklyn Large Leather Bag $495 at Macy’s

4. Fall Festival Favorites

I live in New Jersey, and it seems that everywhere I turn, there’s a Lunar Faire, sunflower farm, or some other festive fall activity to partake in. This look will carry me through it all, because it’s polished with a structured corduroy top, but the jeans add a laid-back quality that won’t feel over-the-top. My favorite part of the look is the hat, which has a cute Ralph Lauren-inspired bear that takes it “from simple to cool girl,” according to Coe. She likes it because it can be worn anywhere — even to a casual evening at a friend’s house — but still looks polished. 

Polo Ralph Lauren Classic-Fit Cotton Corduroy Shirt $148 at Macy’s	7 For All Mankind Modern Dojo High-Rise Wide-Leg Trouser-Style Hem Jeans $178 $125 at Macy’s
Franco Sarto Luella Square-Toe Zip Ankle Booties $180 $107 at Macy’s	Frasier Sterling Teddy Baseball Hat $42 $29 at Macy’s
Lauren Ralph Lauren Gold-Tone & Tortoise-Look Small Hoop Earrings $35 at Macy’s

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