The List: These Are The Best Holiday Gifts To Buy for The Stylish Guy On Your List — Or Yourself

A classic men’s jacket from Taylor Stitch — made to be gifted and made to be worn all winter and into next year.

‘Tis the season to shop for the best Christmas gifts for every stylish guy on your list … yourself included. That brings us quite literally to a new edition of The List, featuring top holiday gifts for stylish guys — and quite likely, a few you’ll want to pick up for yourself. In this case, it could be the rugged, remarkable Taylor Stitch Long Haul Jacket as shown above (one for you and one for me!?) … or it could be something else. We’ve talked recently about things like how to dress for a holiday party and how to upgrade your blue jeans, and these gear picks toe that line nicely — seasonally friendly, made to be given as gifts, and classic enough to wear the rest of the year. Not bad at all. Start shopping!

Disclosure: Portions of this article include gifted products. Portions of this article also include affiliate links. All opinions are my own. 

Taylor Stitch Long Haul Jacket (Huckberry Exclusive) — $188

An unstoppable winter jacket from an unstoppable (and perfectly giftable) brand. Well-done, Taylor Stitch.

If you’ve shopped for yourself or read this blog at any point recently, you know that the Taylor Stitch Long Haul Jacket, with its exceptional fit and remarkable quality, is a thing of beauty. Especially in the Huckberry-exclusive Washed Chocolate Herringbone fabric shown here, it’s one of the best winter jackets you can buy (and gift!),and a true sign of quality. If you or someone you  know are in the market for a tough, rugged jacket, you’d be hard-pressed to find one as exceptional as the Taylor Stitch Long Haul Jacket.

Bertucci A-2TR Vintage GMT — $246.50

A perfectly rugged watch for you or for the watch aficionado on your list.

Now, this won’t be the last time we’ll be talking about a rugged casual watch on this list — far from it, in fact. For outdoor holiday expeditions & cozy, laidback winter evenings around the fire, the classic Bertucci A-2TR is one of the best casual watches to buy right now.

Triple F.A.T. Goose Reizen Jacket — $350

A cozy, durable, investment-worthy winter parka from a classic brand.

Alright, so if you’re giving gifts on a budget, perhaps this Triple F.A.T. Goose parka isn’t the one to buy. But if you want to invest in one of the best men’s parkas for yourself before the polar vortex hits, step right up to the plate.

Flint and Tinder 10-Year Sweatpants — $98

Classic sweatpants made to last a long time.

This, of course, is neither the first nor the last time you’ll read about Flint and Tinder menswear this season on the blog — and as ever, that’s for good reason. The Flint and Tinder 10-Year Sweatpants are perhaps the best sweatpants on the market, and that’s just how it goes.

Kamik Griffon C Boots — $110

Rugged, hard-working winter boots that can take a beating this season.

Looking to buy and wear — or gift — some of the best men’s winter boots this season? Heck, some of the most affordable boots on the market, period? The Kamik Griffon C have you covered for snowy, windy winter days aplenty — and if you or someone you knows spends a ton of time outdoors, this purchase pays off handsomely.

Huckberry’s Huckberry Beanie — $28

Yes indeed, Huckberry is making a stylish beanie cap for all of your winter adventures (and gift-giving).

For just $28 via Huckberry, you’re getting one of the best men’s winter hats on the market, and it’s priced well enough that you can buy it as a stocking stuffer, and then pick one up for yourself. Don’t underestimate the importance of a stylish men’s beanie this winter.

Taylor Stitch Leeward Shirt — $188

A perfectly rugged winter shirt for holiday gifting and holiday style.

Yes, more great holiday menswear from Taylor Stitch — how else would you expect to cover everyone on your list? And of course, there’s something to be said for picking up the rugged, layering-ready Taylor Stitch Leeward Shirt — wear it atop your favorite henley on a chilly winter morning … or gift it to someone who’ll do the same.

Revtown Taper Denim in Smokey Indigo — $79

Slim blue jeans in a pleasing wash, perfect for the guy who needs new jeans this season.

If you’re searching for the most affordable jeans on the market to gift this season — particularly to the guy who needs to upgrade his denim — you’d be hard-pressed to find a better pair of denim than the crisply cut, super-soft Revtown Taper Denim (recently released by the brand).

Outerknown Arcana Sherpa Jacket — $198

Warm, comfortable and utterly wearable all holiday season from Outerknown.

If you or a loved one could use an upgraded from the typical company branded fleece, then the Outerknown Arcana Sherpa Jacket is easily one of the best casual winter jackets you can reach for. Layer it atop a rugged chambray shirt or keep it even more laidback with your favorite henley (and be sure pass along those styling tips if you’re gifting it, too).

Lensabl Eyeglasses and Replacement Lenses — Starting at $77

My pick for stylish glasses from Lensabl. The perfect gift for the glasses wearer!

The time to pick up a last-minute gift fast approaches — and if you know someone who could use the gift of better eyesight (it’s a thing), consider pointing them toward Lensabl (and perhaps starting them off with a stylish pair of sunglasses before diving into the brand’s optical collection). What’s Lensabl all about? You can either pick up a pair of the brand’s stylish glasses yourself, or you can use their lens replacement program to swap in prescription or non-prescription lenses to get lenses with blue-light protection and an anti-scratch coating, among other features. I had a chance to test out the Montana Glasses courtesy of the brand, and I can’t recommend them enough.

Flint and Tinder Donegal Scottish Sweater — $198

It’s hard to find an affordable, made-in-Scotland sweater … or at least, it used to be.

Know a menswear aficionado who appreciates an authentic, vintage-inspired sweater — particularly one made in Scotland? Or just looking for a way to stay warm in style yourself this season? Meet the Flint and Tinder Donegal Scottish Sweater, a truly classic winter sweater made for holiday parties and a timeless Chrismas morning in equal measure.

Minnetonka Moccasins Home & Away Collection — Starting at $44.95

The Tilden shown here from this collection blends style and comfort.

Can moccasins and slippers be stylish? Yes, yes they sure can — and can you wear your Minnetonka moccasins outside the house (within reason, of course)? With the Minnetonka Home and Away Collection, (featuring a suede upper and a grippy rubber outsole), you sure can. They’re stylish enough to pick up a pair for yourself for cozy holiday mornings aplenty, and whoever’s getting these on your list will also love ’em.
Relwen Wool Deck Cardigan — $298 

This tough wool sweater is throwback-inspired and yet entirely modern, and the perfect winter sweater, to boot.

If it’s a rugged winter sweater you seek — or if you simply want to help the stylish guy in your life upgrade his winter sweater collection — you could certainly do worse than the handsome, pleasingly classic Relwen Wool Deck Cardigan. It’s one of the best winter sweaters you can step into this holiday season.
JACHS NY Khaki Corduroy Stretch Blazer — $229

A modern-yet-classic corduroy blazer for perfect holiday style.

Consider this surprisingly stylish corduroy blazer both a holdiay party style suggestion and a potential gift for the guy who needs a better blazer. Either way, JACHS NY nails the balance between classic and modern.
Flint and Tinder Selvage Chinos — $168

A new take on stylish selvage chinos for holiday party fun.

Another edition of The List, and more perfectly rugged Flint and Tinder gear for each and every occasion. Not a bad call, right? These are a new take on classic selvage chinos, here just in time to make someone very happy as a holiday gift — and equally agreeable if it happens to be you shopping for some of the best men’s pants on the market.
Lululemon Escape and Explore Long-Sleeve Thermal Shirt — $98

Innovation and adventure paired with comfort and quality from Lululemon.

For all the fun that holiday parties can bring to the season, there are times when you want to kick back and relax — in style, of course. This innovative Lululemon Men’s thermal shirt, made in partnership with the adventure-minded Wilderness Collective, toes the line between rugged and laidback, easy to layer with a classic hooded sweatshirt, and equally at home when paired up with slim jogger pants at home on a winter weekend.
Bellroy Transit Backpack — $239

These sleek backpack comes with all the bells and whistles you need.

For your holiday travel needs and for the perfect gift for the traveler, the sleek, minimally appointed Bellroy Transit Backpack is absolutely the way to go — it’s sharp, durable and yet rugged, all at once.

Harpoon Spruce Tip Ale — Price Varies

A uniquely rich holiday ale that’s here just in time for the season.

Ever had a rich ale made with spruce tips? No? Now, you have. Northeast brewing pioneers Harpoon Brewery have made the Spruce Tips Ale with ingredients sourced from the Downer State Forest in Vermont, and the results are tasty and well-suited to a chilly winter night, indeed.


Maybe it’s just me, but I think we’ve covered something for everyone here with these gifts and gear picks. Specifically, the Taylor Stitch Long Haul Jacket could just be your new favorite jacket — or someone else on your list, that is. There are plenty of other picks in terms of holiday style and gifting, however, from classic selvage chinos to a rugged casual watch — what’s new and what’s next on your list? Let me know on Twitter.

#OOTD: How to Dress for Your Next Holiday Party This Year

Now, I know what you might be thinking if you’ve got a boatload of holiday party invites: Well, what the heck am I going to wear to this thing? Dressing for your next holiday party isn’t quite as much of a chore as it might seem — that is, if you know where to start, and if you go into said holiday party with an open mind. Whether it’s your office get-together or a small dinner with friends, or a crosstown jaunt to a holiday house party, today’s #OOTD tackles what to wear to a holiday party … the right way, and with ease. To wit: The season should be fun, so throw on a stylish winter blazer, ditch your regular office-hours suit (as stylish as it might be), and step out in a classic flannel shirt, to boot. These picks are accessible and sharp, yet versatile enough for other occasions (if you’ve got a black tie holiday party, then you might want to stuck with that dress code). It’s all about stepping things up accordingly and working with what you’ve already got in your wardrobe, so you’ll also find some stylish Chelsea boots and a sharp leather dress watch along for the ride. We’re not going too far over the top, so this look is anything but stuffy. Crucially, we’re also avoiding a loudly patterned sweater — save that for, well … maybe just leave that one tucked in your closet. There are no novelties or gimmicks in sight here, just a great blazer, slim corduroys and other winter style essentials aplenty. OK, it’s time to get ready. Cheers!

The right combination of refined and accessible for your next holiday shindig.

  • The Blazer: Outerknown Ambassadoar Blazer, $325 — With its soft wool construction and easygoing-yet-polished silhouette, this stylish winter blazer is a surefire holiday party hit.
  • The Shirt: Corridor NYC Check Flannel Shirt, $135 — You’re investing in the best with, well, one of the best shirts for winter. The check pattern is strong and unique, perfectly suited for a chilly winter’s night and perhaps, a sip or three of the best Old Fashioned.
  • The Pants: Flint and Tinder 365 Corduroy Pants, $98 Slim corduroy pants in a rich winter color are about as good as it gets when it comes to holiday party style, right? Right. Flint and Tinder knows how to craft a mighty fine pair of stylish corduroy pants, indeed.
  • The Dress Boots: Rhodes Footwear Huxley Boots, $220 — Sleek, stylish Chelsea boots hardly ever go wrong — especially at a holiday party where the vibe leans more tailored and less casual. And even if you’re heading over to a friend’s house & ditching your shoes at the door, well, these Rhodes Footwear boots still deliver style and functionality the rest of the evening.
  • The Socks: CHUP Montana Socks, $35 — Don’t underestimate the style and power of a great pair of men’s socks, especially if you’re going to be slipping of your shoes at someone’s home. The small details matter, and CHUP assuredly makes some of the best men’s socks on the planet.
  • The Watch: Carpenter Watches G-4 Brooklyn Gent Watch, $724.98 — WIth a crisply tailored yet accessible #OOTD like this one, the best dress watch can make all the difference. And no matter where your holiday party happens to be, you want to look as sharp as possible — Carpenter Watches reliably knows this.
  • The Gloves: Hestra John Gloves, $150 — Staying warm no matter what is critical as you head to your next holiday party — don’t leave home without a pair of the best men’s leather gloves from Hestra, ya dig?
  • The Host Gift: Michter’s US 1 Toasted Barrel Finish Sour Mash, Price Varies — Although you might be more apt to keep this Michter’s whiskey for yourself — and it’s a prime pick-up if you’re hosting a holiday party — this is a fine and seriously premium whiskey for the true aficionado, made with a unique aging process using toasted barrels. The result is one of the best new whiskeys for the season, easily.

Maybe to you, dressing for your next holiday party doesn’t look that much different than any other set of winter style essentials you might find yourself wearing. But in the season of good cheer and giving thanks, it’s all about how you carry yourself, enjoy the evening and also, pull everything together. So the casually rugged flannel shirt you reach for on the weekends can pull double-duty here as a suitably stylish office party shirt, while the stylish winter blazer from Outerknown shown above is well-suited for both the office and post-work day festivities. Heck, you can even add a tie if you  need to step things up a notch, and your stylish corduroy pants also work quite nicely at the office and at that holiday party. For getting to and from the party, you’ll be staying light on your feet AND looking sharp to boot in a pair of stylish Chelsea boots, nicely complemented by some of the best men’s socks for the season — seriously, the small details matter. Because we’re going all-out, you’re going to be wearing the best dress watch on the market (at least, for less than $1,000, that is). Your accessories continue to make all the difference, too, thanks to some of the best men’s leather gloves from Hestra — you won’t miss a beat on any fronts. And whether you’re slinging cocktails with the boss or gifting your host, a bottle of truly excellent Michter’s whiskey never fails. That, to me, represents the perfect ensemble for the season — if you agree, let me know on Twitter! Thanks for reading, and happy holidays!

See Now, Buy Now: The Helm Hollis Boots Are The Perfect Boots for Everyday Wear

Richly crafted leather boots that’ll stand up to plenty of winter wear.

The search for the perfect winter boots is over — your search, that is. You’ve previously seen Helm Boots on the blog (and I’ve long been a fan of this Austin-based brand), but they’ve outdone themselves here. To wit: The Helm Hollis Boots are perhaps the best leather boots to step into at this very moment — read on to find out why, naturally. Now, let’s get one thing straight right off the bat. These aren’t a pair of full-on snow boots (which often sacrifice function for form), nor are they ultra-sleek boots that are almost … too dressy. No sir, these rugged leather boots toe the line between practical and stylish, so while they might not be 100 percent polar vortex-ready, that’s not the point — a well-stocked boot collection features a bit of everything, and the Helm Hollis Boots are simply a darn-fine pair of stylish leather boots. It starts from the ground up with these boots, and that’s a very good thing for December and beyond. We’re talking, in this case, about the use of a mini-lug rubber sole for added traction on slippery streets, topped off with Helm’s white midsole for a bit of signature style and comfort.

SHOP: The Helm Hollis Boots 

Not one, not two, but three terrific color options from Helm Boots.

In short, these are tough leather boots that will age exceptionally well over time, especially in the rich shade of Teak — although they’re also available in two additional colors as shown above. In fact, you might recognize the Hollis Teak Boots from my Instagram — it’s been a  pleasure to wear them these past few weeks through fall and into winter, and I think you’ll feel the same way. The key here is the beautiful Balthazar leather that should age gracefully, while the option to add round or waxed cotton laces gives these a more polished or dressy feel. And in that regard, I’ve found that the Helm Hollis Boots are wearable with everything from slim tan chinos and a chambray shirt at the office to rugged camp pants and my favorite henley on the weekend — without missing a beat, in fact. To make a long story short, I love the Helm Hollis Boots, and I think you will, too.

SHOP: The Helm Hollis Boots 

Disclaimer: This post contains affiliate links, from which a small commission on purchases might be earned. All opinions are my own. Thanks for supporting the brands that support The Style Guide!

Style Pick of the Week: Billy Reid x Huckberry Denim Shirt

There’s no doubt about it — you might have just found your new favorite denim shirt … or your favorite shirt, period!

OK, folks: One of the top menswear brands in the country, one you know and love, is back in a big, big way. We’re talking, of course, about lauded American menswear designer Billy Reid, the man himself and a namesake brand that just gets it when it comes to producing some of the best men’s gear — year in and year out. Take, for instance, the Billy Reid Denim Shirt (or the Billy Reid x Huckberry Denim Shirt, if you want to get technical). It’s one of the best men’s shirts for winter and beyond, made from a seriously cool black washed denim that just so happens to be exclusive to Huckberry. And in a manner of speaking, it could be your new favorite shirt beyond just this season. And that’s not all that hard to believe when you consider the past work done by Billy Reid (as seen on this very site, in fact). We’re talking about stunning, investment-level pieces like the Billy Reid Bond Peacoat just as readily as we’re talking about more accessible basics like the Billy Reid Mini Waffle Henley — from A-to-Z, the quality and classic style is evident through Reid’s namesake line. But back to the remarkable Billy Reid Denim Shirt, alright?

SHOP: The Billy Reid Denim Shirt

Details make all the difference with Billy Reid’s gear, as we well know.

There’s quite a bit that makes this rugged denim shirt so special, from the rich, washed black fabric to smaller details, too. But first, that fabric: The black colorway is a pretty big sticking point, as black isn’t normally a color most guys feel they can pull off (correct? I know I’ve felt that way at times). Especially in a denim shirt, though, it just … works. It’s the right combination of edgy and classic, for starters — and in this case, the Billy Reid Denim Shirt perfectly toes the line between rock concert-ready and office-friendly. Don’t believe me? I’d say you should give the Billy Reid Denim Shirt  a spin with a tan herringbone blazer and faded dark blue denim for some high-low office style. You should also feel free to rock it under a shawl-collar cardigan with olive chinos for yet another office-ready look — and on the weekends, the Billy Reid Denim Shirt is even more ready to go. Case in point: Those same blue jeans you wore to the office will pair up quite nicely with this classic denim shirt — add tan leather chukka boots for some seriously cool contrast. Then, throw on your favorite moto jacket and belly up to the bar. You’ve found your new favorite shirt, yes indeed.

SHOP: The Billy Reid Denim Shirt


The Friday Read: The Best Men’s Leather Jackets, Stylish Men’s Gifts & Your New Favorite Shirt

A rugged winter shirt fit for all your winter weekend adventures.

Looking toward the weekend? Looking toward shopping some new winter style essentials? I know that’s a YES from me on both accounts. In fact, perhaps the rugged Topo Designs Wool Shirt is on your holiday wish list as seen above? It’s one of the best shirts for winter, apt for layering atop a rugged thermal shirt or heck, a cool concert tee. In fact, speaking of concert tees, I’m looking forward to perhaps picking up a new addition to my collection tonight — I’m heading out to Brooklyn Steel to see indie rockers San Fermin play my favorite venue in the city, with an opening-band assist from equally excellent Brooklyn indie rockers Wild Pink (the makers of one of my favorite albums last year!). When you add in the fact that newly opened brewery 18th Ward Brewing sits mere steps across the street from my favorite venue, well, I’d say that’s a recipe for a great start to the weekend, yes? Yes indeed! The rest of the weekend, I’ll be enjoying Prospect Park and a tasty Old Fashioned or two around the borough. I’ll also be sipping on some rich, delicious Driftaway Coffee — you might recall the brand from my Black Friday sales post, and if you want sustainable and ethical coffee delivered right to your door, there’s hardly a better brand to shop. Of course, it’s also prime holiday gifting season — with that in mind, I give you the best way to start your weekend: Another edition of The Friday Read. Enjoy, and cheers to December!

  • Speaking of gift-giving right off the bat, I coverd 15 stylish gift ideas for men over at GearMoose, ensuring that you’ve got plenty of options — from outerwear to accessories — for the style-minded fella in your life (or yourself!).
  • Let’s stick with GearMoose for a second, shall we? On that note, I wrote all about the best leather jackets for men, from brands like Filson and Taylor Stitch — if you haven’t experienced that first snowfall yet, then there’s hardly a more reliable layer than a tough leather jacket for pairing with your favorite henley and slim blue denim.
  • Lastly, have we talked about a unique way to switch up your men’s shirting rotation? Well, I’m sure we have lately … but we haven’t talked about how an elbow patch shirt can upgrade your winter style — these shirts are fit to be worn on their own or atop a classic white T-shirt or a rugged henley in equal measure.

That’s going to wrap up today’s winter-centric, gift-centric start to the weekend — but wait, there’s more! If you’re still on the hunt for the best gifts for men to take care of the style-minded gentlemen on your list, you might want to check out my roundup of the best winter gear. Parkas, leather boots, tough shirting — it’s all taken care of when it comes to the top new winter style essentials, trust me. OK, that’s all for this weekend!

See Now, Buy Now: Get the Perfect Jeans for Winter with Mott and Bow’s New Denim

Highly stylish men’s jeans from Mott and Bow to kick up your holiday style.

Is there ever a bad time to shop for some of the best new men’s jeans? To be quite frank … well, no, no there’s not. Especially when the jeans in question come from NYC’s Mott and Bow, the direct-to-consumer denim brand that’s jumpstarted the men’s denim scene in the past five years (as you know from reading this blog, perhaps!). They’re making some of the best men’s jeans by focusing on affordability, quality and designer touches, all the while offering helpful touches like a Free Home Try-On program for select pairs. And to help shake up the doldrums of winter and improve your holiday dressing, take it from: You need to buy a pair of the Mott and Bow Slim Stone Jeans to wear to the office, then to a casual happy hour … and out again on the weekends. Now, we’ve talked plenty in the past about how Mott & Bow consistently churns out some of the best men’s denim, and that’s no more true than right now.

SHOP: The Mott and Bow Slim Stone Jeans

The other excellent thing about Mott and Bow jeans? The range of styles and fits — including the handsome-yet-edgy Slim Stone Jeans in a perfectly faded grey — means there’s something for everyone. That is to say, whether you know a guy who’s into a pair of Skinny fit jeans or more inclined toward the brand’s Straight-Fit jeans, it’s worth considering gifting some stylish men’s denim this Christmas — if you know a guy who’s been wanting to upgrade his jeans, go for Mott and Bow. The 9-month wash and use of substantial-but-not-too-heavy 11.5oz. cotton also make these jeans agreeable enough to wear with everything from a classic Oxford shirt and a navy blazer to a thermal henley and your favorite leather boots. With that being said … the first step is buying a pair of Mott and Bow jeans for yourself … or someone else. Happy shopping!

SHOP: The Mott and Bow Slim Stone Jeans

The List: This Is the New Gear You Need to Buy Right Now for Winter

Good enough for the great outdoors, more than good enough for you.

Alright, my friends. Saddle up for rugged winter style with the Flint and Tinder Waxed Trucker Jacket shown above, and let’s get ready for December (and beyond, of course). Perhaps you’re already well-versed in the wonder that is the Flint and Tinder Flannel-Lined Waxed Trucker Jacket, crafted in a highly versatile silhouette from tough Martexin sailcloth … and if you haven’t yet checked out this jacket, now is the perfect time. Gift it to yourself, gift it to your friends … just start getting ready for the holidays now. You’ll find plenty more winter style essentials in today’s edition of The List, and know that we’re just getting started. (Oh, and this won’t be the last you hear about that stylish waxed trucker jacket this month, either).

Flint and Tinder Flannel-Lined Waxed Trucker Jacket — $220

But one of the incredible colors in which you’ll find this jacket available via Huckberry.

We told you it wouldn’t be the last time you’d heard about the Flint and Tinder Flannel-Lined Waxed Trucker Jacket this season … and that’s a very good thing, indeed. This premium waxed trucker jacket is available in a whole slew of richly crafted, seasonally friendly colors like the one shown here and at the top of the page, and it could be your new favorite winter jacket. Layer it up underneath a rugged parka for even more added warmth, or rock this tough waxed trucker jacket all on its own atop a warm flannel shirt — that’s prime winter style activated, folks.

HELM Boots Hollis Boots — $350

Beautifully rugged boots made to last for years to come.

Maybe you thought you had your boot collection for fall and winter all sorted out? Well, hold the phone — if you don’t have a pair of the Hollis Boots from Austin-based Helm, your collection of rugged leather boots isn’t quite settled for the season yet. Rugged and versatile, these stylish leather boots are at home with your favorite pair of broken-in denim or with a pair of slim wool trousers in equal measure. And if you’ve been searching for a pair of boots to wear to your next holiday party, simply put … these are the ones.

Bertucci A-2T Super Classic Watch — $170

As dependable a casual watch as it gets.

Looking for the toughest casual watch on the market? The kind of rugged watch you can wear with everything from a denim shirt and a shawl-collar cardigan to a tough waxed trucker jacket and your favorite leather boots? My friends, the Bertucci A-2T is precisely that watch.

Nobis Alpha Men’s Flight Bomber Jacket — $695

A crisp, rugged, classic bomber jacket to wear all season.

With a handsome blend of technical functionality and rugged style, this Nobis bomber jacket is at once old-school and modern, especially in the seasonally appropriate shade of Navy shown here. Wear it with a classic grey henley and faded blue denim for everyday style, or team it with a crisp white Oxford shirt and tan chinos for a mix of high and low. Oh, and it’ll keep you warm as heck all winter long, to boot.

Aymara Eddy Cardigan — $270

A beautiful cardigan to wear in situations both dressy and laidback.

Make no mistake: The Aymara Eddy Cardigan is the sort of beautiful sweater that’s utterly iconic, totally classic and perfectly ready for holiday parties and relaxing winter weekends aplenty. It’s a uniquely vintage-inspired sweater that’ll wear handsomely with slim corduroy pants and rugged leather boots.

Moral Code Jacques Leather Boots — $248

Both refined and yet rugged, these are the perfect boots to take you into the holidays.

Winter is nothing if not the perfect time to break out your favorite pair of leather boots (or rather, your new favorite pair). From holiday parties to days on the road and at the office, the super-sharp, seriously refined Moral Code Jacques Leather Boots are dressy and yet versatile. They feature a rubber outsole for grip on slippery winter streets, and this profile will look at home with dark blue denim and classic wool trousers in equal measure. A fun fact: You might recognize these from my Instagram, where I’ve had the chance to test ’em out as of late.

AIAIAI All-Round Preset Modular Headphones — $145

Sharp, crystal-clear headphones to upgrade your travel listening experience.

For long hours on the road during the holidays, the right tunes (the music of The National, anyone??) or a cool podcast are the way to go — and these stylish over-ear headphones are sleek, essential and seriously well-made.

Michter’s US-1 Toasted Barrel Finish Sour Mash Whiskey — Price Varies 

A wonderfully crafted whiskey to warm your soul on a winter night.

There’s perhaps no more fitting spirit to sip on a cold winter night than a richly crafted whiskey, especially one you can experience on the rocks and get all the flavor and character you expect. That’s what Michter’s Whiskey has done with the remarkable Toasted Barrel Finish Sour Mash, which improves upon the distillery’s award-winning sour mash whiskey by aging it custom-made barrels (toasted, not charred, critically). The result is complex and multi-layered — a fitting whiskey to add to your bar cart or bring as a gift to your holiday host. Cheers!

Stetson Cromwell Outdoor Hat — $71

A rugged, outdoor-ready hat for plenty of winter adventures.

Let’s keep things rolling on the “rugged winter gear” front here, shall we? And if you want a classic hat to pair up with your Flint and Tinder Flannel-Lined Waxed Trucker Jacket, well, the Stetson Cromwell Outdoor Hat is the right way to go. Perfectly cool and classic.

United By Blue Responsible Flannel — $78

The right mix of rugged style and responsibly sourced fabric and construction.

It’s true — if you don’t have a rugged flannel shirt in your wardobe yet (especially as we roll through the holiday season), this is the one to buy. The United By Blue Responsible Flannel has a ton of upside, seeing as it’s made with organic cotton and recycled polyester — both of which are responsibly sourced. Plus, the resulting shirt is super-soft and stylish, with a modern fit that wears well with everything from grey chinos to tan corduroys to your favorite pair of laidback denim. Buy one for yourself, gift one for someone else … there’s no wrong way to go.

Free Fly Flex Henley — $65

A perfectly comfortable-yet-rugged henley for a winter weekend.

There’s no doubt in my mind, winter is perhaps the perfect time to layer up with a rugged henley — like the Free Fly Flex Henley, for example. The Heather Denim color also wears nicely with … the aforementioned United By Blue flannel shirt!

Flint and Tinder 365 Pants — $98

Slim five-pocket pants in a perfect holiday color.

If you’re still searching for the perfect pair of pants for the holidays, the Flint and Tinder 365 Pants are the right way to go, featuring a classic slim cut and a rich, holiday-friendly Oxblood color. Wear them with a classic denim shirt and sleek leather Chelsea boots to a refined holiday gathering.

Deschutes Brewery Da Shootz! Pilsner — Price Varies

A clean, light, refreshing pils to stock in your fridge this season.

For all this talk about rich winter cocktails and whiskey, and equally rich food, what about for all those times when you want to lighten things up and refresh your palette? This holiday season, that’s when you’re going to want to reach for the Da Shootz! Pils from Deschutes Brewery, a cleverly named, light, refreshing (and low-cal!) beer to sip on at many a holiday party. Again, cheers!

XD Design Bobby Duffel Anti-Theft Travel Bag — $150

A sleek travel backpack made to prevent theft of your valuables — not bad at all.

The best bag for holiday travel is one that’s sleek, minimal, easy to lug through a crowded airport, and yet highly functional at the same time. That’s a lot to live up to, but the XD Design Bobby Duffel is actually an ideal anti-theft travel bag, made with hidden zip closure and no front access. The only thing stopping you are holiday crowds, really.


Which of the above gear picks are you scoping out this holiday season? Maybe you’re in the mood for a tough waxed trucker jacket to step in snowy weather? Or maybe you’re looking forward to sipping on some rich Michter’s whiskey or a light Deschutes Brewery lager? Can’t forget about a vintage-inspired sweater  for all those holiday festivities, either. However you dress for the season, feel free to let me know on Twitter.