#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!

#OOTD: How to Wear the Best New Boots for Guys This Fall

Seeing as we’re cruising through fall, there are a couple things that are pretty clear in my mind in terms of men’s style essentials. For starters, you need a pair of the best boots for men on your feet ASAP. What’s more, you need a functional pair of boots that also happen to look great — while also offering what you might call more unique style. And above all else, you need to know how to wear boots this season, especially when the boots in question are the rugged-yet-refined Season Three Ansel Hiking Boots out of New York City. Featuring the cut of a hiking boot but some of the refined touches of your favorite dress boots, you’ll recognize plenty of versatile complementary pieces to help you get ‘out and about (safely) this season.

From a tough field jacket to a rugged men’s henley, the layers on your top half are every bit as “ready for anything” as your new favorite boots. And on your bottom half, you’ll recognize classics like slim dark blue denim and perhaps the best leather belt and the best men’s socks, all compiled with an eye toward helping you navigate the city, head upstate, get out on a day hike and grab a cold beer at an outdoor (socially distanced!) beer tent afterwards. How does that sound? This #OOTD is nothing if not versatile, so you should keep on scrolling to check it out below. When you build from the ground up with a pair of the best boots for men this season, darn near anything is possible.

Pair up versatile hiking boots with casual, rugged classics for fall.

So, that’s it. That’s today’s #OOTD. It’s a versatile combination of both adventure gear — heck, just check out that exceptional Ollech & Wajs Pilot Watch — plus gear picks that can do a bit of everything (naturally, the centerpiece Season Three Ansel Hiking Boots get the job done). The rest of this ensemble works well in or out of town, especially around a backyard bonfire on a crisp fall night. You’re staying warm with one of the best men’s henleys from Buck Mason, and you’re layering up in rugged, classic fashion with the Filson Field Flannel Shirt for timeless fall style — how about that? Classic slim blue jeans from Mott and Bow tie things together in a way that’s just a bit more versatile than technical hiking pants, and the epically cool Todd Snyder Made-in-New York Field Jacket looks great, provides tough functionality and works with anything in your fall wardrobe.

Naturally, your supporting cast is what’s going to set this #OOTD apart, so the best leather belt from Billykirk is a reliable style move. To keep your feet comfortable in style, I’m a huge proponent of the American Trench Merino Activity Socks — and to ease into your evening with some bourbon whiskey in hand, how about switching on some of the best Bluetooth headphones from the good folks at Master & Dynamic? Taken together, this ensemble provides rugged style, performance, durability and some seriously cool style for fall — can it get any better than that? I don’t think so. If you pick up any of these pieces, feel free to let me know on Twitter. Happy fall, my friends!


#OOTD: How to Wear Your New Favorite Summer Boots (Seriously)

Our ongoing #OOTD series rolls on, and in perfect summer style, too. “But wait a second … boots? In the summer? How does that work?” Ahh, well, my friends … it works something like the below ensemble. A man of taste has a lot of ground to cover these days, from knowing how to wear a short-sleeve shirt to how to rock chukka boots this season. That being said, it’s fun to switch things up from straightforward summer classics every now and again as these months wear on. Today’s pick — stylish Chelsea boots from Astorflex — checks all the right boxes.  Today’s #OOTD just gets it right (in my humble opinion) on a number of fronts. Again, lightweight boots are the perfect way to build a look from the ground up, accented by an equally lightweight summer shirt and easygoing chinos. I won’t spoil the whole look, though — you’ll need to keep reading for the rest. But in this day and age, where is the below look taking you? For starters, it’s going to work quite alright to hang out around the house, the bonfire or the back patio (that’s what the stylish home speaker seen below is for). Aside from that, things are quite a bit different beyond your front door. I’d say this is the kind of go-to summer style you can wear to work from home, and you can assuredly take this look for a spin as you pick up to-go cocktails or coffee — hey, it’s the new normal, right? Sharp style is an everyday thing, and shaking things up from your reliable summer style essentials even slightly can prove useful and enjoyable. As ever, you’ve got to start things out from, quite literally, the ground up. So, let’s check out how to wear your boots this summer — enjoy, folks.

Chelsea boots to ground this outfit, teamed up with plenty other style essentials.


OK, folks. Who’s onboard with wearing your new favorite boots for summer as often as possible for the rest of the season? When you take a look at the men’s style essentials they’re teamed up with, it becomes all the more feasible to consider. Take an organic cotton shirt from Flint and Tinder to keep things casual and breezy, then keep that pace moving right along with organic cotton chinos in an easygoing fit and fabric (plus, a cool-as-heck Navy color). Your new favorite chinos are nothing without some classic men’s socks to accessorize alongside those lightweight Chelsea boots, so make sure you pick up a pair of those, too. Elsewhere, you’re putting plenty of style points up on the virtual scoreboard with an iconic Todd Snyder x Timex watch — it’s seriously one of the coolest watches for guys that your author has seen in some time. Because this look is suited for work or play, and for drawing up ideas at home or heading into the office via social distancing, a Bellroy work folio is going to help you keep your everyday carry essentials in check. And particularly if you’re at home (and especially if you happen to be entertaining), the best audio equipment can enliven any space — that’s where Tivoli Audio gets it done. Certainly, some stylish summer sunglasses tie this whole look together in a way that says you’re cool and stylish, but know how to buckle down when the time comes. After  all, isn’t that what every #OOTD should do?