#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 Men’s Chukka Boots This Summer

If I’ve said it before, I’ve said it a million times. The summer heat is no reason to relegate your chukka boots to storage. Why, just last month here on the blog, we talked about the best leather chukka boots you can buy for spring, the sort of pair that blends proper durability with style points and handmade craftsmanship. Those chukka boots, in fact, are back in a big way today as we explore yet another #OOTD, this one focused on, well the best way to wear chukka boots for summer. The key is keeping it light, breezy and casual-yet-cool, because the best chukka boots for men are the kind you can wear with mostly anything in your wardrobe, and just about anywhere (even to the office, once you check out the iconic dress watch in this ensemble). It helps that today’s featured chukka boots come from Veldskoen, which has a storied history of making chukka boots for hot weather.

When you don’t quite want to lace up canvas sneakers and it’s also far too hot for sturdy leather work boots, chukka boots are a great go-between. Especially if you’re spending time around and heading somewhere that requires a bit of polish and style (patio cocktails, anyone?), the best men’s chukka boots are just what the (style) doctor ordered. The supporting cast is packed with summer style essentials, including a stylish short-sleeve shirt from Huckberry. Tread carefully, select the best boots for summer and relish in the fact that you’ll have these Veldskoen chukka boots far past this season. Happy shopping, my friends.

The best way to wear chukka boots this summer

  • The Chukka Boots: Veldskoen Leather Chukka Boots, $179 — When the time comes to reach for dependable summer shoes, consider rugged-yet-lightweight, classic men’s chukka boots.
  • The Shirt: Wellen Hemp-Cotton Button Down, $68 — Keep things nice and breezy up top with this sustainable hemp-blend shirt from Huckberry.
  • The Lightweight Pants: Marine Layer Saturday Pants, $125 — These stylish drawstring pants look like chinos on the surface, but wear like comfortable sweatpants. Perfect for breezy summer days aplenty, and they’re possibly the best pants to wear with chukka boots.
  • The Socks: Mack Weldon AIRKNITx Ankle Socks, $18 — Get that “no socks” look without resorting to going barefoot. These comfortable ankle socks are the right accessory to keep you on your feet with functionality in mind. Oh, and Mack Weldon offers free shipping, too.
  • The Grooming Essential: Triumph & Disaster Coltrane Clay, $30 via UNCRATE — Shape your fresh, post-quar haircut with one of the best hair clays for men, folks.
  • The Watch: Shinola Runwell Leather Watch, $1,095 — Here’s the kind of stylish leather dress watch you can wear to the office and then to happy hour, or else to a cool-as-can-be summer party on the weekend, without missing a beat. The Shinola Runwell never fails, easy as that. 
  • The Sunglasses: Pacifico Optical Buckler Sunglasses, $195 — A sleek and on-trend #OOTD like this requires some of the coolest men’s sunglasses, like these round-frame shades in a crisp colorway.
  • The Everyday Carry: Mission Workshop 500D Drift Tote, $235 — Perhaps you’re not quite in need of a rugged tote bag like this one, but if you’re going to be out and about all day, it pays to pick up this much-loved Mission Workshop tote.

Does this #OOTD have you looking ahead to warmer days without much on your agenda besides getting another ice-cold beer at your favorite bar? Wherever you go — even if you decide to wear your new favorite chukka boots to the office — I’d say it’s well-suited to any style demand you can dream up. Start out with classic men’s chukka boots to set the tone (more casual than dress shoes, more polished than sneakers). Keep it breezy from there with a sustainable button down shirt from Huckberry, then throw on the best pants to wear with chukka boots to really drive home this effortlessly cool look.

Keep the details on point, too: A pair of comfortable ankle socks are a surprisingly underrated move when wearing chukka boots and straight leg pants (roll ’em up just a bit to show off some ankle). Shape your hair accordingly with one of the best hair clays for men, a nice way to put a bit of extra effort into this #OOTD. No matter where you go, a stylish leather dress watch is going to polish things up quite nicely with sharp looks, too. Elsewhere on the accessories front, some of the coolest men’s sunglasses will top this look off handily. And to haul your EDC picks, you know what to do: Grab the Mission Workshop tote and load it up at well. For expert, laidback-yet-cool summer style, you’ve just found the best men’s style essentials. Cheers, folks!

#OOTD: How to Wear Chukka Boots For Summer — The Best Way

I know what you might be thinking right off the bat: Chukka boots? Isn’t it the middle of summer the time to put those away already, even if they happen to be some of the best lightweight boots out there? Well … maybe. But not quite. No, in fact, you can still wear your favorite chukka boots this summer — the trick comes with choosing a lightweight pair of chukka boots, then styling ’em up with laidback summer style essentials that won’t slow you down. Even if you’re just hunkered down at home, as we all seem to be these days, the best chukka boots for men can still be put to good use. How so? And when? Well, first of all: You’ll find these Astorflex chukka boots have been paired with, among other crucial summer style staples, a Buck Mason henley for breezy, easygoing summer style. So, there’s that. And as to when you can wear the best suede chukka boots … I’d say anytime you darn well please, from flipping burgers on the grill to kicking back with a beer in hand (don’t worry, we’ve got your new growler included in today’s ensemble, as it were). Various other pieces are here to put in a solid effort, too — take a rugged indigo work shirt as your ideal summer evening layer, for starters. This #OOTD also features some style hacks you can put to good use when the time does come to get back out in public. Note the layering of said henley under a denim workshirt, and the subsequent denim-on-denim combination. I’ve probably said too much already, though — you should check out this stylish summer ensemble yourself below.

Classic suede chukka boots to wear all summer — yes, that’s right.

  • The Chukka Boots: Astorflex Greenflex Chukka Boots, $104.98 — As mentioned above, you can certainly still wear some of the best men’s chukka boots into June and beyond — naturally, Huckberry delivers some of the best chukka boots on the market, made with lightweight construction and smooth suede.
  • The Henley: Buck Mason Pima Short-Sleeve Curved Hem Henley, $48 — Yes, we’re back once again with a Buck Mason henley, and it’s the right base layer for this breezy outfit. In fact, it’s one of the best short-sleeve henleys for summer, available at a quality price.
  • The Workshirt: Flint and Tinder Indigo Work Shirt, $82.98 — Here’s the thing with day-to-night style this summer — it can go from sweltering to breezy once the sun goes down, and even if your only plans involve kicking back on the porch, beer in hand, a rugged indigo work shirt from Flint and Tinder still gets the job done.
  • The Denim: Buck Mason Maverick Slim Jeans, $145 — When you get sick of sweatshorts this spring and summer, step out in some stylish slim jeans in a pleasing medium wash. Buck Mason makes some of the best men’s jeans to complement outfits like this, and that’s applause-worthy in my book. Oh, and don’t worry — these jeans still work with your rugged indigo work shirt, given the different colors. Roll ’em up and show off some ankle.
  •  The Stylish Dive Watch: About Vintage 1926 At’sea, $375 — Now, look — if you don’t want to go too overboard, you might not need this vintage-style dive watch. But if you want to shake up your at-home look while hanging out, listening to a record, manning the grill … throw on this classic dive watch.
  • The Audio Essential: U-Turn Audio Orbit Special w/ Preamp, $549 — Maybe you’re less of a vinyl records guy than a Bluetooth speaker type of guy — but if putting on one of your favorite records, beer or whiskey in hand, is a pastime, then this U-Turn Audio Orbit Special is one of the coolest record players to add to your home or apartment.
  • The Summer Must-Have: GrowlerWerks uKeg Copper Growler (128oz.), $239 — What goes better with a summer afternoon or evening than a cold beer (if that’s your thing)? There’s not much. It’s good news, then, that this rugged growler from GrowlerWerks looks great in your kitchen, in your den or on your back porch. Plus, it’s got plenty of capacity for your new favorite summer beer.
  • The Grooming Essential: Jack Henry Cleanse+, $16 — When you want to refresh your skin after a long summer day, or prepare for getting outside, you want something light, clarifying and of course, cleansing. Enter this face cleanser from Jack Henry.

Terminal Tee

Now, if you’d rather wear your favorite summer sneakers instead of rugged chukka boots in this case, I say go for it — the world is your oyster, as it were. But if you want to shake up your at-home style routine, you can go with no cooler combination than laidback suede chukka boots that build up into stylish summer basics. And that list of basics? It’s pretty great, in my mind. We work from the ground up with the best men’s jeans, a casually easygoing pair in a nice wash that won’t weigh you down as much as a heavy pair of raw selvedge denim might. From there, you’re going to be throwing on one of the best short-sleeve henleys for summer, a base layer that you can easily rock on its own, should you choose. In case you need some protection from the sun, or if you happen to need a light layer when the sun goes down, that’s where your rugged indigo work shirt enters the fold. The Jack Henry Cleanse+ shown above will keep your face fresh and in good shape, while a vintage-style dive watch will undoubtedly keep you on time as you prep dinner or run from room to room to get on that conference call (yes, this #OOTD can be worn to work from home, too!). For when the day’s work is done, I’m going to recommend you kick back with some fresh, flavorful beer from your GrowlerWerks uKeg Growler. Do this all while listening to, say, “Antisocialites” by Alvvays — a favorite vinyl of mine — on your U-Turn Audio Orbit Special. While it’s not the same as heading to a brewery or hanging out with friends, this #OOTD harnesses some of the best gear for summer in the meantime. If you’d like to share what you’re wearing at home this season, head to Twitter and give me a follow. Thanks for reading!

#OOTD: How to Style Your Chukka Boots in Classic Fashion for Spring

There’s a lot that you can do with a pair of dependable, stylish and classic chukka boots — if you read The Style Guide, surely you know this. Or at least, I hope this here blog has been helpful enough. If you still feel like I’ve been slacking (which is entirely possible!), then today’s new #OOTD is here to, well, pick up the slack.  We’re talking how to style your new favorite pair of chukka bootsPerhaps though, these rugged chukka boots — and Astorflex, the brand that makes ’em — aren’t new to you at all. In any case, they’re recently restocked, they’re made from sustainable materials in a classic silhouette, and they’re more than ready to pair up with the gear we’ve got in store for you today. The below outfit is one that just … works. From a casual weekend day of coffee and museum-hopping or a productive day at the office, we’ve got building blocks that’ll stand the test of time, from slim navy chinos to a durable spring jacket to a classic Oxford shirt. Oh, and those chukka boots. Let’s dig into the specifics more, shall we? Read on below.



All your outfit needs is a versatile pair of chukka boots to start things off … yes?

The Boots: Astorflex Greenflex Rough Boots in Sand, $155 —  You know Astorflex for their commitment to craftsmanship and sustainability — no better brand from which to buy essential chukka boots, ehh?
The Jacket: Relwen Sailcloth Tanker, $298 — Because no outfit is complete without an essential spring jacket, the Relwen Sailcloth Tanker is absolutely the one to buy.

The Shirt: Taylor Stitch The Jack in Blue Everyday Oxford, $98 –Is there a shirt easier to style than a truly timeless Taylor Stitch Oxford shirt? I’d wager perhaps not.

The Chinos: CIVIC Frank Chinos, $128 — The partner brand of Taylor Stitch has set its focus squarely on sustainable fabric, tried-and-true designs and neutral, easy-to-style colors — you can find all of that in the CIVIC Frank Chinos.

The Socks: Anonymous-ism Silk and Cotton Socks, $15 — You could certainly wear crew socks with this ensemble, but what say we roll up the CIVIC Frank Chinos and pair ’em with these well-made Anonymous-ism socks?
The Belt: Beltology Radius Woven Belt in Olive, $60 — Because the small details count, a textured casual belt is going to add just enough visual interest to this outfit.
The Boxer Briefs: CIVIC Merino Boxers in Heather Grey, $55CIVIC can even do merino boxers quite well — these are a recent offering from a brand that’s got everything taken care of for you.
The Watch: Nezumi Studios Bailene Watch, $500 — The handsome and crisply designed Nezumi Studios Bailene Watch toes the tricky line between dressy and casual — quite nicely, at that.
As we’ve mentioned before, it really doesn’t get better on the footwear front — at least in terms of transitional spring style — than a pair of essential chukka boots that work for situations in the office and on the weekend. Style these durable boots with the right picks, including the highly versatile CIVIC Frank Chinos and that unbeatable Taylor Stitch Oxford shirt, and you’ve got a look that’s hard to top. Seriously, even just those three pieces can take you to brunch, the bar, a business trip … you name it, they’ll do it. The small details are also going to aid you in terms of comfort and performance — take merino boxers from CIVIC, for instance. And on your wrist? The Nezumi Studios Bailene Watch is as sharp a new timepiece as you’re liable to find around these parts. You also really can’t go wrong with Anonymous-ism socks for a bit of spring-friendly style. To top it all off, you best throw on the durable, weather-ready Relwen Sailcloth Tanker — it doesn’t get better than that, it just doesn’t. So, where will this #OOTD take you? Are there any pieces you’d add or subtract? Let me know in the comments below!
Thanks for reading,

Style Pick of the Week: Astorflex Greenflex Chukka Boots

Astorflex Greenflex Chukka Boots

Classic, stylish and easy-to-wear chukka boots via Astorflex, shown at the top right with travel essentials from Owen and Fred, Abercrombie & Fitch, Huckberry, Nautica, Herschel Supply Co. and Electric Sunglasses.

Is it just me, or is it time for a seasonal footwear upgrade with a pair of the best boots for men? Think: Something that’s not a sneaker, but not a burly leather work boot that’s uncomfortable to wear — something that’ll work for nearly every style situation, from a casual weekend barbecue to a stylish road trip. Who’s with me? Perhaps the Astorflex Greenflex Chukka Boots come to mind — no? I recently took my own pair on a spring road trip to Indiana, and can definitely vouch for them.  They’re an updated take on the classic desert boot, crafted with a crepe sole, high-quality suede and the type of easygoing silhouette that pairs just as well with your favorite chinos as it does with slim light wash denim on breezy summer days. In fact, I’d hope you recognize the Astorflex Greenflex Chukka Boots as seen above from a few posts on The Style Guide.

Namely, the rich Dark Khaki colorway seen here will work as you dress for Sunday brunch or look for ways to upgrade your casual shirt — don’t think you should shelve all of your chukka boots entirely just because the thermostat starts to climb. And know that these Astorflex chukka boots also come in the equally versatile Stone and Grey colorways. Indeed, with a blend of comfort, style and accessibility, the Astorflex Greenflex Chukka Boots — just like the brand’s Astorflex Chelsea Boots —  are a seasonal must-have in any color. Trust me: That goes for spring, summer and fall. Seriously, keep them on hand to wear with a rugged chambray shirt and dark selvedge denim to a fall tailgate — it’s a winning combo if you’re looking for insight into how to wear chukka boots. But, back to matters of summer style — what makes these a must-buy?

For starters, it’s tough to find a chukka boot that features eco-friendly, handmade Italian construction out there — let alone with a sub-$150 price tag. And to find one that goes with everything from slim stone chinos to dark denim to slim light wash jeans in the summer can be tricky, too. That easygoing versatility is what sets these Astorflex Greenflex Chukka Boots apart in so many situations. Rather than resorting to minimal athletic sneakers, jeans and a slim pocket tee, try out these chukka boots and perhaps a tough dive watch — instant style upgrade in the making, and certainly one of the best men’s style moves you can make. And because they’re sold via Huckberry, you can be sure that they’re up to snuff in terms of quality and great looks. It’s also worth noting that the desert boot is a stone-cold classic silhouette — as if you needed another reason to buy these. In addition to real-life functionality for British soldiers, they’ve gained an iconic status — up there with classic white sneakers — that’s tough to top on the footwear front. So, despite summer weather finally catching up to us … there’s no reason not to wear a classic pair of desert boots like the affordable, easy-to-wear and stylish Astorflex Greenflex Chukka Boots.

How would you style these boots? To pick up inspiration from yours truly, check out my Instagram. And send me a note on Twitter if ever you have #menswear questions.

Stay stylish!



Style Pick of the Week: Red Wing Heritage Weekender Chukka

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

Huckberry Red Wing Chukka

Pair up lightweight chukka boots with a crisp pair of dark denim for a casual and patriotic weekend combo.

With it being the Fourth of July and all, we’re very much in a patriotic spirit here at The Style Guide. That carries right on over to footwear, and today’s made-in-America Style Pick, the Red Wing Heritage Weekender Chukka. Great footwear has been a focus as of late on the Style Pick series, including stylish leather sneakers fit for summer. But given that lots of us are hitting the road this weekend, there are certain things that should be in your bag and on your feet when it comes to what to wear for the Fourth of July. Crucially, a crisp, durable pair of chukka boots is a great way to upgrade your travel style. Seriously, a pair of chukka boots works with light wash denim casually, and fits right in alongside tan chinos for a more monochromatic, tailored look. The Heritage Weekender Chukka has just about everything you need for the weekend, too — note that sizes are somewhat limited (size 9-13), but as the boots run a half-size large, you might be all set to shop. Onto the specs — the Weekender Chukka is crafted from roughout leather that’s water, stain and perspiration-resistant, so it can tackle any hiking or walking across the weekend in style. Plus, the quality is self-evident, as it’s produced using S.B. Foot Tanning Company leather (just as the brand has done for decades on end). Still not sold on wearing boots in the summer? Bear with me — or walk with me?

Red Wing Heritage Weekender Chukka

A relatively trim silhouette, casual roughout leather and classic Red Wing styling touches make these worth the investment.

The Weekender Chukka takes a more casual, nuanced and lightweight approach to the silhouette, so it won’t weigh you down as much as a heavier pair of rugged winter boots. The Hill outsole is flexible yet dependable and durable, and the eye-catching striped yellow laces are a nod to classic Red Wing style. The brand’s ComfortForce footbed should also add to their wearability — an extra bit of reinforcement is critical when standing around waiting for fireworks or grilling out. Plus, the contrast stitching provides another point of visual interest, making them an even more casual pair of chukka boots. These are definitely chukkas you can rock with slim navy or olive chinos and a heather grey pocket T-shirt this weekend and beyond. And they’ll do just as well when worn with a slim short-sleeve henley and light chinos in a high-low style combo during other summer excursions. As to the rest of your style picks this weekend? Grab a durable weekender bag and maybe some other essential Fourth of July gear, and you’ll be set.

Get your pair of the Red Wing Heritage Weekender Chukka now (hurry!).

Enjoy the weekend, and go forth in style!


Buck Mason - Timeless Design. Made in America.