Style Scenario: A Trip to the Pumpkin Patch

About the Author: Adam Terry is a thirtysomething salesman in the construction industry. He enjoys whiskey, watches, boots/shoes, family time, 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 weekend day at our local farm’s pumpkin patch park. Some of us are excited for the large petting zoo and pony rides, while others are just looking to have a relaxing and low-key afternoon in the sunshine with a cool breeze at our backs. Either way, it’s usually 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 daydreaming about what kind of outfit is best to maximize comfort and convenience without looking like an unkempt schlub next to my gorgeous Leaf Peeper of a wife. Since you’re imagining this sartorial adventure with me today, let’s plan it together. Ideally, our get-up should be pieced together with versatile, everyday clothing items that are easily attainable and affordable by the Average Joe. We want clothing items that can be reworn time and time again, over the years, to maximize their value. However, let’s not forget that we’re Dappered guys/gals and we like stylish and well-curated outfits, too. Check this out:

The Jacket: J.Crew Sussex Quilted Jacket – $119.50 ($198). For most of us, a lightweight jacket on top of a flannel or button-down type shirt is usually sufficient during these transitional fall days. I like this one from J.Crew because it’s incredibly versatile thanks to its classic style, comfortable cut, earthy color palette, and lightweight quilted insulation that’s just enough to keep that chilly air at bay. Currently 40% off as part of their mid-season sale. No code needed. Not final sale either, which is nice.

The Shirt: L.L. Bean Scotch Plaid Flannel Shirt – $60. Great characters wear great flannel shirts. Take a trip back through TV time and see for yourself: John Goodman in Roseanne, Bob Saget in Full House, Tim Allen in Home Improvement, etc. You simply can’t go wrong with a soft, button-down collar flannel shirt. I like this one from L.L. Bean because it easily pairs well with both jeans and chinos with its warm and neutral color palette.

The Pants: Bonobos All Season Jeans in Dark Rinse – $29.40 FINAL SALE w/ FLASH40 ($99). Many guys love their rigid Levi’s and that’s fine, but some of us prefer a bit of stretch for our day to day routines. I recently picked up a pair of these All Season jeans from Bonobos and I’m happily impressed. The fit is great, the fabric is soft and breathable, and they have just enough stretch so that I don’t feel like they’re getting in my way when I’m playing tag on the playground with my kid. If you’re in need of new blue jeans, aim for a more versatile pair with a darker rinse.

The Belt: L.L.Bean Men’s Essential Leather Belt – $45. I recently reviewed this leather belt and was surprised at the level of value that you can still find for less than $50. These belts are well made, readily available, and backed up with L.L. Bean’s bulletproof warranty and returns policy. An unbeatable value and made in the USA. Full review here.

The Sunglasses: Kent Wang Browline – $55. Something to provide balance against the crunchy ruggedness of the boots and flannel. Tortoiseshell frames have all those fall colors cascading through them, while the classic frame design brings up mental images of leafy fall campuses. Incredibly comfortable. Acetate and metal frames. 50mm lenses don’t wear overly small. Should fit most average to smaller sized heads. Shown at the very top of the post on the Pumpkin. Not sure why the Kent Wang site makes them look flatter than they are in person. Seems like their image scaling might be wonky on that particular product page. They’ve got classic clubmaster proportions though. Nothing to be concerned about.

The Watch: Timex Marlin Automatic 40mm Leather Strap Watch – $259. Simple and utilitarian, this automatic Marlin features a clean face, forgoing distractions. 40 hour automatic reserve, stainless steel case, domed acrylic crystal, and an S.B. Foot Tanning Company brown leather strap.

The Socks: Darn Tough “The Standard” Light Cushion Mid Calf Socks – $26. As Joe recently said, Darn Tough’s “The Standard” socks are those socks that are perfect for almost every occasion. Over the past few years, I’ve slowly switched out all of my other tall socks for these and have absolutely no regrets. Made in the USA with a lifetime warranty. Yes, they’re expensive at ~$25 a pair, but they’re worth every penny. You won’t regret it, either.

The Shoes: Blundstone #585 Chelsea Boots – $220. These Blundstone boots are the perfect pair of do-it-all boots for most guys who enjoy a casual, elevated “Average Joe” aesthetic. If you’re heading to the pumpkin patch and plan on walking through dirt, mud, and muck, you’ll appreciate a pair of boots like these that are easy to pair and wear, comfortable on foot, and rugged enough to hose off after a long day. Full review here.

The Snacks: An apple cider slushie and a few cider donuts – $20. No trip to the pumpkin patch is complete without some tasty fall-inspired snacks to keep you happily fed. My wife and I love the apple cider slushies and cider cake donuts that our local joint offers, but it’s the powdered sugar funnel cakes that get me out of the bed in the morning. Yum!