#OOTD: How to Dress for a Fall Evening On The Town — The Right Way

So, you’ve done your research, you’ve made your reservation and you’re looking forward to an evening at your favorite cocktail bar, a secluded whiskey den or an old-school speakeasy — if it’s a special occasion, and even if it’s not, I’d bet you’re now on the hunt for what to wear out on a fall evening. Date night, weeknight, post-concert, pre-dinner … the right #OOTD can go a long way in terms of solidifying rock-solid fall and winter style, and I’m here to help you put it all together.

My go-to in a situation like this is usually my trusty Flint and Tinder Trucker Jacket, to go along with my neighborhood whiskey bar, Sycamore Bar and Flower Shop, but perhaps you want to step it up a notch (NYC’s The Dead Rabbit ought to do the trick!). Wherever you go, the best men’s style essentials are crucial in that regard — we’re talking subtle but stylish, considered and composed. Witness our picks below, from slim black jeans — sharp but not too stuffy — to rich cognac leather boots and more unique touches suited to an evening on the town. Case in point: Layers like a rugged work jacket and slick-but-classic touches like an organic cotton Oxford shirt. Of course, you’ll also find the best leather dress watch in this ensemble for the taking. The key here is putting together a look that’s sharp, versatile and comfortable — in my mind, this is a get-up you could wear to the office, and then right out to dinner afterwards. It all comes together in a fall-friendly black-and-tan combination that’ll quietly turn heads, and hopefully, impress your company. Like the look of this? Feel free to reach out to me on Twitter. 

Pairing up rich leather boots with dark denim and a workwear jacket — all in the pursuit of great whiskey.

  • The Slim Dark Denim: Bluffworks Travel Jeans 2.0 in Black Dark Wash, $98 — Invest in the best with these slim black jeans in a flattering fit — built-in stretch and handy hidden pockets ensure your everyday carry essentials are taken care of, while the silhouette is dressy enough for a refined bar or speakeasy.
  • The Jacket: Vetra French Moleskin Jacket, $229 — A modern update to the classic workwear silhouette, this rugged work jacket provides a nice contrast to your slim black jeans and white Oxford shirt — it’s casual but not too casual, and visually interesting all the same.
  • The Shirt: By Garment Makers Organic Shirt, $78 — A crisp, classic white Oxford shirt is a foolproof move, no matter the occasion — and when the occasion involves enjoying an Old Fashioned alongside pleasant company, well, you’d best look the part. This might just be the best Oxford shirt to snap up for fall and winter.
  • The Boots: Moral Code Jacques Wingtip Boots, $249 — The right leather boots can really tie an outfit together — and the pair of the moment has to be this pleasingly refined pair from Moral Code, featuring classically rugged brogue detailing. Certainly sharp enough for a distillery, a speakeasy or your favorite cocktail bar.
  • The Watch: Carpenter Watches G2 Brooklyn Gent, $724.98 — For a refined evening out and about, only the best leather dress watch will do. Carpenter Watches makes a nuanced, subtle and yet visually interesting timepiece, to say the least.
  • The Everyday Carry Essential: Rustico Traveler’s Notebook and Wanderer Pen, $120 — Especially when visiting a new locale (and even when visiting an old haunt), a stylish leather notebook will come in handy when inspiration strikes — or when you simply want to remember that exact cocktail recipe.
  • The Socks: Taylor Stitch Merino Socks, $22 — Don’t discount the importance of stylish socks, especially this comfortable, anti-odor pair from Taylor Stitch.
  • The Leather Wallet: Bellroy Slim Note Sleeve, $89 — Stay sleek, streamlined and stylish with a slim leather wallet that keeps your valuables safe — no extra bulk required.

From top to bottom, head to toe, I’d say you’re not going to go wrong with this look for an evening enjoying your favorite cocktails. We’re keeping your look fresh and modern by swapping a blazer for a rugged work jacket, and then pairing up that piece with a classic white Oxford shirt for go-anywhere seasonal style (and yes, you can wear that combo at the office, too). From there, slim black jeans help carry the day by providing a nice mix of edgy style and a sharp silhouette — again, critical if you’re visiting a hip haunt in town. Of course, the right pair of rugged leather wingtip boots has to be what makes this outfit all work; the pair shown here from Moral Code are practically begging to be worn out on a fine fall or winter evening. Excellent essentials are also critical to keeping your ensemble streamlined and stylish, from a slim leather wallet to stylish socks and of course, stylish leather notebook to jot down tasting notes, recipes or random musings. And when hitting up your favorite cocktail bar, the small details seemingly get a bit bigger — take your wristwatch, then upgrade it from the average with the best leather dress watch — then prepare to watch the compliments roll in. This ensemble might look a bit different from the look you were first envisioning, and in my mind, that’s A-OK — it’s all about unique style and nuanced, subtle details. This look might even make your whiskey taste that much better — but again, that’s all up to you. Thanks for reading, and happy whiskey hunting (and tasting!).

The Friday Read: Michigan Craft Beer, Shinola’s New Watch & The Best Boots for November

If you didn’t feel in the holiday spirit yet, well, step right this way with these rugged Rancourt boots.

Although I’ll be in Brooklyn this weekend (likely wearing a pair of rugged leather boots very similar to the excellent Rancourt & Co. leather boots shown above!), my mind is back on my home state of Michigan, and in particular, my alma mater, Michigan State University. I was just in East Lansing last weekend for a terrific time with old college friends, filled with beers at HopCat (a staple of my senior year) and Crunchy’s, along with some Michigan State football. It’s of course with football in mind that I’ll be enjoying craft beer back in my new home borough this weekend — it’s Michigan vs. Michigan State on Saturday, after all! It’s a rivalry that meant a lot to me as a student, and means even more now that I’m farther away from campus. I’ll be finding a sports bar in Brooklyn to hunker down for the game, likely followed by a round of (hopefully!) celebratory beers at the always-excellent Threes Brewing. If your plans involve college football as well, I wish you nothing but luck! And if they involve more frenzied pursuits — such as starting your holiday shopping early — then I’d suggest you A) Check out the below Friday Read and B) Check out the never-not-outstanding Huckberry 2019 Gift Guide, packed with gear like the above Rancourt & Co. leather boots, plus plenty of stylish stocking stuffers. In the meantime, the below reading and gear picks ought to get you started — agreed?

  • Let’s get this weekend started accordingly the right way, yes? I’m talking, of course, about one of the best new beers to try now, covered by yours truly at GearMoose. That beer would be the rich, utterly satisfying Perrin Brewing S’more Stout, a fittingly inspired beer for cold Michigan (and New York) winters. I can’t wait to get my hands on some when I’m back in the Mitten State.
  • Speaking of my home state of Michigan — as has been on my mind this week — it only makes sense that Shinola would come up in conversation here. In fact, over at GearMoose once more, I covered the Shinola Bronze Monster, a durable, tough-as-heck timepiece with plenty of style points built right in. Did I mention it draws design inspiration from Detroit’s Prohibition smugglers? Yes, it’s got plenty going for it, too. Wear it with your favorite henley and tough chore pants on a chilly winter weekend.
  • OK, let’s keep it rolling when it comes to rugged weekend gear and perhaps more importantly, rugged winter boots. I covered the Danner Pub Garden Boots here on the blog just last week, and if you missed that feature, now’s your chance to catch up. They’re fit for the trail, the town, and indeed, the pub, easily. They’ll also wear particularly well with, say, a classic Barbour jacket and rugged work pants.

OK, those are all the style quick hits and men’s style news updates I’ve got for you this week. If you’re still searching for the best gifts for everyone on your list (and it never hurts to start as early as possible!), well, then head to my roundup of some of the best gear for November. From flannel shirts to chukka boots to the best whiskey glasses for the spirits lover, that post has something for everyone (if I do say so myself). OK, it’s time to get ready for some football. Cheers!

See Now, Buy Now: The Danner Pub Garden Boots are the Must-Buy Boots For Your Closet

Rugged boots that are ready for anything you can throw at ’em.

There’s a good chance that any time you set your sights on buying a pair of the best men’s boots, you turn toward Danner — at least, if that’s not the case right now, you need to fix that ASAP. That’s because the dependably rugged and surprisingly stylish Danner Pub Garden Boots are simply some of the best men’s boots for fall, crafted to reliably take on tough projects and laidback fall and winter days in equal measure. If at first you seem skeptical that one pair of tough leather boots could do so much, think again: After all, we’re talking about the Pacific Northwest-inspired folks at Danner, and they know a thing or two about delivering versatile men’s boots (as you’ve probably read on this blog, no doubt!). The Danner team has taken a multi-faceted approach with the Pub Garden Boots, starting with a tough leather upper guaranteed to break in over time (while withstanding mud and slush, that is). They’re waterproof and made to keep your feet dry, no matter what — and the use of a comfortable Ortholite footbed provides added protection on top of that. Those specs make these boots decidedly work-ready, yet they’ve still got plenty of style to bring to the table (or the trail, or the brewery … you get the picture).

SHOP: The Danner Pub Garden Boots 

This rich Chocolate colorway also brings plenty of style to your footwear rotation.

To be sure, the Pub Garden Boots really do blend the best of both worlds — Danner’s proprietary Bi-Fit Board construction offers added ankle support and durability throughout the whole length of the shoe. Again, these are work-ready boots — if you really want ’em to be. Plus, the outsole is made with an oil and water-resistant compound to offer maximum grip on slippery surfaces — that’s important whether you wear the Pub Garden Boots to the brewpub (pun intended!) with your favorite pair of jeans or to hit the trail on an early morning hike. The silhouette is rough-and-tumble, perfect to wear through fall and winter with rugged chore pants and a thermal henley. Long story short: If you want a pair of stylish leather boots that can do it all, you want the Danner Pub Garden Boots.

SHOP: The Danner Pub Garden Boots 

Style Pick of the Week: Taylor Stitch Moto Boots in Weatherproof Suede

Impressively rugged, functional and stylish Taylor Stitch moto boots.

If you thought your closet was positively too full of gear from Taylor Stitch … well, think again. And if at the same time you’ve been looking for the perfect pair of fall boots, you’re in luck. The Taylor Stitch Moto Boots are here to save your day — and your fall and winter wardrobe — from certain peril in snowy and slushy weather. Now, you’ve read about these stylish moto boots in my guide to wearing black jeans, and they’re back again for good reason today. The Taylor Stitch Moto Boots carry on an impressive lineage of top-notch performance and effortless style from everyone’s favorite San Fran-based brand, and that’s all the more reason to snag your pair now. That is to say, everything that you love about Taylor Stitch‘s chambray shirts, handsome sweaters & rugged outerwear gets distilled into one of the best pairs of men’s boots for fall and winter. What makes the Taylor Stitch Moto Boots so essential, even in spite of a slightly higher price tag ($348, for those curious)? The difference, as ever, remains in the details — from the rich 4oz. snuff suede to the impressive Goodyear welt construction., made to be resoled when you need it the  most. And of course, these are highly unique in that they just so happen to be a truly weatherproof pair of suede boots, something not many other brands can say. Does that make ’em some of the best men’s boots? Yes, indeed it does — but there’s a whole lot more where that came from.

SHOP: The Taylor Stitch Moto Boots

A tough sole and stellar design details put these Taylor Stitch boots a cut above the rest.

Notably, these rugged suede boots can stand up to plenty of wear in nasty weather thanks to that durable weatherproof suede and Goodyear construction — they’re complemented by a tough Vibram outsole, to boot (pun very much intended). Make no mistake, these aren’t a pair of boots to be messed with, and that goes for whether you wear them with your favorite black jeans and a henley, or team them with slim navy trousers and a classic Oxford shirt after a snowy work day commute. Throw in waxed cotton laces for a bit of tailored appeal, then add in the fact that antique brass hardware finishes off the Taylor Stitch Moto Boots, and you’ve got a truly unbeatable pair of the best fall and winter boots — that’s not just talk. Perhaps the best part about these? They’ll work with the rest of your well-stocked Taylor Stitch wardrobe … so, what more can you ask for? Not a whole lot.

SHOP: The Taylor Stitch Moto Boots

Style Pick of the Week: Astorflex Bootflex Boots

Step right into fall with these richly crafted, rugged leather boots.

Are you sick of hearing about Astorflex boots yet? Hopefully not: The brand is a longtime favorite of your humble menswear writer, and they simply make some of the best men’s boots for fall (and beyond, for that matter). With all of that being said, the above criteria makes the Astorflex Bootflex Boots the perfect leather boots for fall — and a natural fit for a late September Style Pick of the Week as we really get into the best season for menswear. What makes Astorflex boots so special? That’s a prime question indeed, my friends. As you’ve read in the past, it all starts with the right approach in terms of design and construction. In the case of the Astorflex Bootflex Boots, that means they’re made with premium European leather aged in oak barrels for 30 days — just the right amount of time to get that perfectly lived-in look and feel, right out of the box. All-natural ingredients soften the leather even further before it’s finished off with top-notch construction via a perfectly casual natural rubber sole. These are, again, some of the best men’s boots you can buy, with a difference that’s noticeable from the second you try them on.

SHOP: The Astorflex Bootflex Boots

Easily wearable with your favorite pair of dark denim — and plenty of other fall style suggestions.

Now, let’s say you feel you’ve already got enough leather boots in your arsenal … well, A) You can never have enough leather boots and B) You surely don’t have a pair akin to the Astorflex Bootflex Boots in terms of style and versatility. The crepe rubber sole means these aren’t cut out for all types of terrain, but for traversing a new city on a fall weekend getaway or heading out to your favorite brewery? Wear the Astorflex Bootflex Boots, accented with slim dark denim and a thermal henley, or try them with olive chinos and a classic chambray shirt. These tough leather boots will also age beautifully the more you wear them, and the unlined leather lining means they’ll provide all-day comfort with seriously minimal break-in time. Weekend tailgate? Early brunch? A day at the office (navy blazer in tow)? The Astorflex Bootflex Boots are here for you. And the price is ultimately what could be the kicker — finding stylish leather boots under $200 is a quest all its own, yet Astorflex delivers on that front handsomely. Happy fall, my friends.

SHOP: The Astorflex Bootflex Boots

 

See Now, Buy Now: The Rhodes Felix Chukka Boots are the Best Chukka Boots To Buy This Fall

The best men’s chukka boots for your hard-earned cash this season? They very well might be.

So, is it high praise to call a pair of rugged chukka boots the best pair of chukka boots out there? Indeed, it is — but the very good news for you, my friend, is that the Rhodes Felix Chukka Boots really are the best men’s chukka boots for your time and money. Again, that’s high praise, but rest assured, these stylish leather chukka boots (as sold by Huckberry, naturally) are up to the task. Now that we’ve nearly reached the end of September, it would behoove you to really gear up for fall — and that starts with your footwear rotation. The right pair of chukka boots can take you to the office, to the beer bar, out on the road and everywhere in between — and believe me, I’ve worn the Rhodes Felix Chukka Boots all of those places, and then some (you might have seen ’em on my Instagram, to wit). Available in rich calf leather options like Tan Nubuck and handsome iterations like Oak Suede, these classic leather chukka boots are as good as it gets, from the silhouette (sleek yet not too dressy), to the functionality (grippy and durable, thanks to the studded rubber outsole).

SHOP: The Rhodes Felix Chukka Boots

Sleek, stylish, versatile chukka boots you won’t be able to get enough of — I guarantee it.

And as with all manner of stylish gear from Huckberry, the hits keep coming — in spades, at that. The Rhodes Felix Chukka Boots deliver the goods through resoleable Blake stitching on the sole, which means you’ll have them for years. What’s more, the option to customize them with dressier flat waxed cotton laces means that these are even the kind of chukka boots you can wear with a suit this fall (and beyond, naturally). But lest you think these are only the kind of boots to wear through fall and then stow come winter time, think again. The handy, functional Texon insole delivers insulation when you need it — keep these classic chukka boots on hand to wear with everything from slim dark denim and a thermal henley to a rugged flannel shirt and classic tan chinos when snow starts to hit. Yes indeed, you’ve really never seen a pair of chukka boots like the Rhodes Felix Chukka Boots — that’s a fact.

SHOP: The Rhodes Felix Chukka Boots

Style Pick of the Week: Rhodes Dean Boots

Sleek, dependable leather boots to get you in the spirit of fall (slowly but surely, of course).

OK, folks. Bear with me here: Although it’s still August, why are we talking once more on the blog about the Rhodes Dean Boots (as seen here)? There’s still plenty of summer left, to be sure, but there’s never a bad time to grab a pair of the best men’s boots — and besides, the Rhodes Dean Boots are sleek, stylish  & affordable, plus they’re available for a heck of a deal at Huckberry. Again, bear with me here — perhaps, the heat is so bad in your neck of the woods you can’t bear the thought of putting on rugged leather boots. And that’s OK! The earlier you can start prepping for one of the best seasons in menswear (that’d be fall), the better. There’s really no better place to start building out your cadre of fall style essentials than your collection of rugged leather boots — trust me on that.

Every guy needs a great pair of leather boots in his closet for when temperatures take a turn downward, and the great part is, if you can’t stand to wait until September or October to break out the Rhodes Dean Boots, they’re actually lightweight enough to be worn with, say, slim light wash jeans and a short-sleeve henley in August. It all starts with the little details. Crucially, you’re getting the sort of quality and style you expect from Huckberry, seeing as they’re made in Portugal from premium materials like rich, premium calf leather designed to resist odors and provide breathability at the same time.

A sleek toe shape that still manages to convey rugged style.

SHOP:The Rhodes Dean Boots

You’re also getting the ability to mix and match as you go along — for instance, the Rhodes Dean Boots come in both cap toe (as seen above) and plain toe options, all the better for going slightly more rugged or slightly more sleek. And given the fact that the Rhodes Dean Boots are available in rich, early fall-ready colors like Rust (my personal favorite) and Honey, they’re a wise investment to make up front. Of course, they wouldn’t be a pair of the best leather boots without design touches like a Texon insole with an anti-shock foam layer (crucial if you happen to be wearing these to a brewery or a rock concert). And small details like speedhook lacing and raw leather laces offer up the rugged styling you crave when it comes to a pair of the best leather boots. Again, while it might seem early to be thinking about picking up a pair of the Rhodes Dean Boots, it’s truly never too soon to plan ahead.

SHOP:The Rhodes Dean Boots