#OOTD: How to Wear Chukka Boots for Fall For Guys

Is there any pair of footwear more essential for early fall than chukka boots? And not just any chukka boots, but the very best chukka boots you can get your hands on? Think of chukka boots like the perfect go-between as you step from summer into fall. They’re not as bulky as hard-wearing snow boots or duck boots, nor are they as lightweight and breezy as your favorite summer sneakers. The right pair of chukka boots, easily some of the best boots for men this season, is wearable with tan chinos and an Oxford shirt back at the office, or else with a rugged henley and expertly faded jeans on the weekend. And today’s pair in question checks all the right boxes, particularly if it’s durable style you want. And if you haven’t yet gotten acquainted with the Astorflex Greenflex Chukka Boots, it’s high time you got started.

These rugged-yet-versatile leather chukka boots are the kind you can wear just about any day of the week, and it helps that they’re stylish and sustainable to boot. Natural rubber soles meet environmentally friendly construction, and the result is a pair of chukka boots made to break in over time, not wear out. No doubt about it, the Astorflex Greenflex Chukka Boots are going to become your new seasonal go-to. I think you’ll also appreciate the supporting cast alongside your new favorite boots, including rugged fall outerwear and essential men’s pants. The rest of today’s #OOTD is up for grabs below, so shop accordingly. Stay stylish!

  • The Chukka Boots: Astorflex Greenflex Chukka Boots, $195 — Here they are: The centerpiece of your next fall ensemble and some of the best men’s boots for fall, period. They’ll only get better and better the more you wear them.
  • The Fall Jacket: Faherty Stretch Terry M-65 Jacket, $288 — Faherty has taken the field jacket and made it supremely comfortable, using easily wearable stretch cotton terry fabric for a modern, streamlined finish.
  • The Fall Shirt: Flint and Tinder Stretch Canvas Expedition Shirt, $118 — For wearing to the office on a casual day, for working from home and for grabbing beers this fall, get this garment-dyed Panama canvas shirt that’s just the right blend of comfortable, rugged and versatile.
  • The Jeans: Mott and Bow Slim Crosby Jeans, $108 — The right pair of jeans is as essential to your fall #OOTD as the chukka boots shown here, and Mott and Bow makes a nicely priced pair with a classic fit and wash.
  • The Socks: Flint and Tinder Wool Camp Socks, $18 — A pair of the best men’s boots for fall isn’t worth all that much without the best men’s socks as a much-needed accessory. These are warm, retro-inspired and ready for anything.
  • The Watch: Shinola Runwell Quartz Watch, $595 — To complement your perfectly rugged chukka boots, get an equally rugged, super-sharp brown leather watch from a brand that knows how to deliver expertly crafted style.
  • The Everyday Bag: Mission Workshop 500D Drift Tote, $285 — This rugged and durable tote bag has been a favorite of the blog this season, all owing to the fact that it can haul your laptop and electronics, or else some fall picnic essentials. Make it your next EDC essential now.
  • The Fall Hat: Buck Mason Rib Cotton Cashmere Seafarer Beanie, $60 — When fall weather turns unexpectedly chilly, break out this soft cotton cashmere hat (after storing it in the pockets of your Faherty M-65 jacket, of course.

How’s that for a rugged-yet-up-for-anything fall #OOTD? You can customize this ensemble to your liking, perhaps swapping out that Faherty field jacket for a fall-ready blazer, but really, the chukka boots in question are what makes this #OOTD really tick. As I’ve said before, from the price tag to the construction, they really are some of the best men’s boots for fall, and that’s just a fact. It gets even better from the ground up though, from a pair of Mott and Bow denim to the right socks to accent this outfit in fine fashion. And your accessories are only going to drive home the point even further (that this is an outfit fit for the brewery or for a casual office setting). Take the Shinola Runwell Quartz Watch, a truly remarkable timepiece that’s both rugged and refined. You’re also going to want to throw on that Buck Mason beanie when cold weather hits on that fall road trip you’ve been planning. Of course, a rugged Flint and Tinder shirt is just the kind of shirt you need to wear, sleeves rolled up, as you hit the road or head to the office. If this #OOTD looks like it’s got what you need, be sure to let me know in the comments below. Happy shopping!