Style Scenario(s): A Trip to the Pumpkin Patch

About the Author: Adam Terry is a thirtysomething salesman in the construction industry. He enjoys watches, whiskey, shoes/boots, and working on his dad bod father figure.

From traditional wedding attire to smart casual office wear to casual weekend BBQ party vibes, our Style Scenario series features curated outfits built around many different, very common life events. Browsing through a handful of these curated options can help generate some fresh style ideas and give you some direction before you decide on exactly what you’re going to wear. Remember, these are just some inspirational ideas and not rigid guidelines. Have some fun!

Every autumn, my family likes to plan a day or two at our local pumpkin patch park and entertainment venue. Some of us are looking to get outside to touch some grass and have a relaxing, low-key afternoon in the sunshine with a cool breeze at our backs (that’s me). Others are excited for the massive petting zoo, pony rides, and overpriced pumpkins. Either way, it’s a great opportunity to take the kid(s) for a playdate and get everyone out of the house for a bit.

With this trip in mind, I’ve been planning an outfit that will maximize comfort and convenience without looking like an unkempt schlub next to my gorgeous Leaf Peeper of a wife. Let’s not forget that we’re Dappered guys/gals; we like stylish and well-curated outfits, so this list won’t be limited to comfort-first athleisure. Instead, our get-up should be pieced together with versatile, everyday clothing items that are easily attainable and affordable by the Average Joe. We want to focus on items that can be reworn time and time again, over the years, to maximize their value. Heck, you probably already own something similar to a few of these items! Check them out:

NOTE: With weather being as unpredictable as ever, we’re giving you two style scenarios… One for cooler autumn temperatures, and another for those areas which are still feeling the long tail of summer hanging on.

 

Cooler Weather

The Jacket: L.L. Bean Field Trip Shirt Jac – $74.99 ($99). L.L.Bean’s Field Trip shirt jac is the ultimate fall layering piece, offering just enough warmth and structure to complete a sophisticated weekend outfit without the bulk of an insulated jacket. Its lightweight construction makes it easy to shed when it gets too warm or add back on when the autumn breeze picks up, giving you the flexibility to adapt to fluctuating fall temperatures throughout the day. Worn over a knit sweater and oxford shirt, it adds a rugged, outdoor-inspired edge that balances the refined layers beneath, creating an effortlessly upscale yet approachable look that’s perfect for everything from Instagram-worthy photo ops to the barnyard petting zoo.

The Sweater: J.Crew Basket-Stitch Cotton Crewneck Sweater – $84.50 ($118). J.Crew’s basket-stitch cotton crewneck brings textural interest and a splash of seasonal color to any fall wardrobe, with its tactile knit pattern adding visual depth that elevates a simple jeans-and-boots combination. The saturated, muted hues echo the natural tones of autumn foliage while remaining neutral enough to pair effortlessly with medium wash denim and brown leather boots for a cohesive, smart casual look. Its 100% cotton construction provides a smooth, non-itchy handfeel and is the perfect weight for layering or wearing solo during those crisp fall days when the temperature hovers between cool morning and mild afternoon.

The Shirt: J.Crew Broken-In Organic Oxford Shirt – $98. An oxford cloth shirt serves as the ideal foundation layer for a sophisticated fall outfit, with its crisp texture and relaxed, yet slim fit providing structure beneath a knit sweater and chore coat. The soft, lived-in feel of the fabric ensures comfort during all-day wear while the classic oxford weave adds a refined touch that keeps the layered look polished rather than purely utilitarian. Its button-down collar and placket create clean lines that peek out from under your sweater, adding dimensional interest and a smart-casual sophistication to an otherwise relaxed weekend outfit.

The Jeans: Made in the USA Flint and Tinder All-American Stretch Denim – $158. A good pair of stretch denim in a medium wash can be the perfect base for a layered fall outfit, with a straight fit and slight taper creating a clean, modern silhouette that complements brown Chelsea boots without excess fabric bunching at the ankle. The versatile medium wash acts as a neutral canvas that allows your textured layers – a chore coat, knit sweater, and oxford shirt – to shine while maintaining visual balance throughout the outfit. The added stretch becomes essential when you’re chasing down your kid at the pumpkin patch after they’ve been fueled by apple cider donuts and a splash-and-dash of sweet tea, ensuring you can move freely and comfortably through hayrides, corn mazes, and impromptu games of tag among the pumpkins.

The Sunglasses: Huckberry Weekenders Sunglasses – $60. Huckberry’s Weekender sunglasses are the perfect accessory for sunny fall days at the patch, offering 100% UVA/UVB protection. The warm tortoise pattern echoes the rich browns in your boots and belt while the forest green lenses tie beautifully into your moss green sweater, creating a cohesive autumnal color story. They strike an ideal balance between practical and stylish; rugged enough to toss in your pocket between photo ops with the kids, yet polished enough to maintain the smart-casual aesthetic of your thoughtfully layered outfit.

The Snacks and Gifts Bag: L.L. Bean Zip Hunter’s Tote Bag w/ Strap – $60. The L.L.Bean Zip Hunter’s Tote Bag in camo (woodland or khaki olive) is the unsung hero of any pumpkin patch excursion, offering ample space for snacks, small purchases from the gift shop, and those inevitable wardrobe changes when your kid emerges from the corn play pit covered in husk debris. The zippered top keeps everything secure while you’re navigating hayrides and photo ops, and the adjustable strap lets you carry it comfortably whether you’re hauling pumpkins or chasing sugar-fueled toddlers. The camo pattern adds a rugged, outdoor-appropriate aesthetic that complements your fall outfit while being practical enough that you won’t worry about dirt, spills, or the general chaos that comes with family adventures.

The Shoes: Astorflex Bitflex Chelsea Boots – $275. On your feet, you’ll want a supportive boot in a mid to dark brown shade that strikes the perfect balance between rustic charm and everyday practicality for a weekend pumpkin patch outing. These Bitflex Chelsea boots from Astorflex have a rich, earthy brown color and warm tone that complements the autumn landscape while the soft nubuck leather provides comfort for walking through a corn maze. The crepe sole offers excellent grip on uneven (dry) terrain without sacrificing style to a chunkier lugged sole. These boots effortlessly transition from dirt pathways to the cozy cafe afterward, making them an ideal choice for your day that’s full of fall festivities.

The Belt: Flint and Tinder Vintage Leather Belt – $85. Flint and Tinder’s vintage leather belt in brown is the perfect finishing touch for your fall-focused outfit, visually adding warmth to the palette to co-exist with your medium wash jeans and brown boots. Its full-grain leather construction will age beautifully and can handle the rigors of some light outdoor adventures while maintaining a polished look that elevates your casual weekend wear. The classic design works seamlessly with the rustic autumn aesthetic, adding a subtle layer of refinement without feeling overdressed for a day of hayrides and apple cider slushies.

The Watch: Hamilton Khaki Field Quartz 38mm Field Watch – $445. Hamilton’s Khaki Field Quartz 38mm is the quintessential daily driver that effortlessly bridges utilitarian toughness with refined style, making it ideal for everything from weekend adventures with the family to casual corporate work dinners. Its military-inspired design with a bead-blasted stainless case, black dial, faux-vintage cream indexes, and green textile NATO strap with brown leather keeper loops create a natural color harmony with fall’s earthy palette. It will complement that cream-colored chore coat, green sweater, indigo denim, and brown leather boots without feeling overly coordinated. The rugged build and simple quartz movement can handle the rigors of a pumpkin patch outing while maintaining a sharp, understated presence that elevates your smart casual style with a touch of vintage-inspired sophistication. If you have the spare coin and appreciate hand-wound mechanical watches, upgrade to the Khaki Field Mechanical instead.

The Socks: Darn Tough Unisex “Bone Ranger” Crew Lightweight Socks – $24. Darn Tough’s Bone Ranger lightweight crew socks in navy blue and orange add a playful seasonal wink to your polished fall kit without tipping into novelty territory. The skeleton and pumpkin head motifs offer just enough whimsy for a pumpkin patch outing, while remaining subtle enough that you’re accessorizing with personality rather than becoming “that guy with the loud socks”. They’re the perfect way to acknowledge the season’s festive spirit while maintaining the sophisticated, smart-casual aesthetic of your layered outfit, proving that upscale doesn’t have to mean uptight. We acknowledge that Darn Tough’s are not cheap, but they’re made well and, with proper laundering and care, should last until you become a Bone Ranger.

 

 

Warmer Weather

The Shirt: Wills AloeKnit Polo Shirt – $78. A polo is the ideal choice for those unexpectedly warm fall days at the pumpkin patch, offering the polished look of a collared shirt without the stuffiness of a traditional oxford and all of the breathability of a t-shirt. This one from Wills is cut from a Peruvian pima cotton blend and infused with aloe (wait, really? yes really) for cooling, sweat-wicking, and anti-odor properties to keep you comfortable during those active moments – running through the corn maze, picking up pumpkins, or attempting to keep up with your overly energetic kids. The breathable knit construction provides superior airflow compared to densely woven fabrics, making it perfect for those sunny autumn afternoons when the temperature climbs but you still want to maintain a smart-casual aesthetic.

The Pants: Nordstrom Slim Straight Stretch Jeans – $100. Nordstrom’s slim straight jeans with a hint of stretch offer an elevated alternative to shorts, striking the perfect balance between polished and comfortable. The soft hand feel from the garment wash and subtle stretch fabric ensures breathability and freedom of movement, which is essential when you’re bending down to pet the goats, climbing on tractors, or chasing down your apple-cider-slushie-fueled kid through the playground. They provide more coverage and refinement than shorts while remaining comfortable enough for active outdoor adventures, proving that looking put-together doesn’t mean sacrificing practicality on a sunny afternoon.

The Sunglasses: Kent Wang Aviator Sunglasses – $55. Kent Wang aviator sunglasses offer timeless style with modern optical quality, featuring gold-toned frames and premium Mazzucchelli CR-39 polarized lenses that provide 100% UV 400 protection for those bright fall days. The 54mm lens size strikes an ideal balance for most face shapes, offering generous coverage without overwhelming your features, while the classic aviator silhouette adds a touch of vintage cool that complements smart-casual weekend wear. While none of us are Tom Cruise in Top Gun, we can all benefit from the polarized lenses which help to cut through glare, whether you’re driving to your weekend destinations or enjoying outdoor activities with the family. The warm gold tone creates a cohesive look when paired with brown leather accessories like watch straps, belts, and boots for a refined autumnal aesthetic.

The Watch: Orient Bambino 38mm on Leather Strap – $295. Orient’s Bambino 38mm automatic watch is a masterclass in accessible luxury design, offering exceptional value with its elegant champagne dial, blued dauphine hands, and exhibition caseback that showcases the F6724 automatic movement with hand-winding and hacking functions. The 38mm stainless case and domed mineral crystal create a classic dress watch profile that punches well above its price point, while the brown faux crocodile leather strap adds warmth and vintage charm that pairs beautifully with fall’s earthy color palette and your smart-casual weekend wear. With a 40-hour power reserve, date complication, and versatile 20mm lug width for easy strap changes, it’s the perfect daily wearer that transitions effortlessly from weekend adventures to slightly dressier occasions, though its 30m water resistance means you’ll want to remove it before any serious water activities other than simple hand washing.

The Belt: L.L. Bean Comfort Waist Stretch Nylon Belt – $50. The L.L.Bean Comfort Waist belt strikes a great balance between casual functionality and understated style, making it ideal for relaxed weekend wear for trips like this. The navy blue strap, brown leather accents, and bronze-toned buckle add warmth and visual interest to elevate it beyond a basic leather belt, while the stretch nylon construction ensures all-day comfort… especially during active pursuits when your kid sprints away from the haunted house at a speed that would make Usain Bolt jealous. This belt is the kind of versatile accessory that can pair effortlessly with chinos and a polo for a smart casual look that’s polished enough for a “reservations needed” dinner, yet won’t feel overly dressy if you’re stopping at a meat and three.

The Socks: Made in the USA American Trench Retro Stripe Socks – $14 FINAL. American Trench’s retro stripe socks bring a touch of nostalgic Americana to your fall wardrobe, with their classic crew sock design featuring subdued blue and green stripes against an unbleached cotton background that subtly complements the seasonal color palette of your outfit. Made in the USA from domestic materials, the medium-weight cotton/nylon/acrylic/spandex blend material and cushioned footbed provide all-day comfort whether you’re walking through weekend markets or exploring the trails looking for bigfoot. Speaking of that fabric blend, the added nylon and spandex add levels of durability and just enough stretch to stay in place, making these socks a practical yet stylish foundation piece that pairs equally well with sneakers for casual weekend activities or peeking out from under jeans with your favorite boots.

The Shoes: Veja V-10 Sneakers – $160. Veja’s V-10 sneakers are the ultimate versatile footwear choice that effortlessly transitions between smart-casual and sporty aesthetics, making them perfect for any weekend fall activity. Paired with a knit polo and garment-washed jeans, they provide comfortable, stylish support that’s ideal for farmers markets, casual brunches, or leisurely strolls through the petting zoo while maintaining a polished, put-together look. Their clean, minimalist design also allows them to dress down seamlessly with a graphic tee and athleisure shorts on warmer days, proving they’re a true all-season investment that adapts to whatever your weekend throws at you.

The Bag: Clever Supply Sidekick Crossbody Bag – $68. For those who want to maintain a clean, refined silhouette without sacrificing functionality during weekend outings, invest in a crossbody bag like this one from Clever Supply Co. With its compact 1L capacity, the bag easily stashes everyday essentials like your phone, keys, chapstick, earbuds, hand sanitizer, and even a small point-and-shoot camera, if you’re into that. The thoughtful design focuses on organization and keeps everything accessible without having to fumble around for anything. It has one main compartment with four mesh sidewall pouches, a front zip pocket, and a rear phone sleeve. The premium-feeling waxed canvas construction offers durability and weather resistance that looks better with age, while the padded rear surface and wide, seatbelt-style 44″ adjustable strap ensure comfortable all-day wear whether you choose to rock it as a crossbody or belt/waist bag. It’s ideal for warm weather when you want to keep your pockets empty for a smoother, more polished look, proving that practical carry doesn’t have to compromise your smart-casual aesthetic. Plus, it’s way smaller than a tote bag!