It’s undoubtedly rare to have every single gift figured out for every single person on your shopping list, but that’s probably no more true than when shopping for the stylish guys on your list.
Think of it this way: If they’re far and away the most fashion-conscious person in your life, it’s easy to paint them into a corner: They’re impossible to shop for when the holidays roll around. We’re here to tell you to have faith, though — there are plenty of gifts to get the style-obsessed guy, and at prices that won’t break the bank.
And hey, some of the fun about shopping for a style aficionado comes from the fact that you very well might find a piece or two to add to your own list. Of course, in the spirit of giving, we’ll keep the focus on the guy most likely to receive your style-focused purchases.
Beyond that, we’re going to keep affordability in mind, and we’ll walk you through both choice selections and upgrades to those picks in a variety of highly giftable categories. Find the selection that’s best-suited for the fashionisto in your life, and prepare for a very happy holiday come Christmas.
Choice: Craft London Signet 2.0 Ring ($30)
Accessories are sometimes tricky to figure out, but the key is to search for pieces that are elegant and refined, yet toned down. So, stay away from gifting anything too over-the-top or oversized. This signet ring is a perfect example of a unique piece that’s a great way for a guy to dip his toes into a new world of jewelry.
Upgrade: Studebaker Metals Signet Ring ($148)
Featuring a brushed, vintage-style finish and careful, heirloom-level construction, this signet ring is at once luxurious and yet not overly expensive. Plenty of sizes are available through J. Crew, and it’s fitting that this toned-down ring will also wear nicely with one of the brand’s Timex watches and a classic chambray shirt. Style aficionados, take note.
Choice: Madewell Corduroy Baseball Cap ($32)
From the winter-ready corduroy fabric to the simple, subtle and logo-free design, this corduroy ballcap is an elevated but still accessible accessory. It can be treated like a grab-and-go cap for winter weekend errands, or worn alongside dressier staples, like a navy topcoat and slim blue jeans.
Upgrade: Ebbets Field Kansas City Katz Vintage Ballcap ($43)
There are standard hats with athletic logos, and there are hats that channel history and sporty style at the same time. Ebbets Field is perhaps the foremost maker of authentic ballcaps, and you can even customize this gift further by snapping up a cap from the recipient’s hometown.
Choice: GAP Brushed Cozy Scarf ($34.95)
Sometimes, standing out stylishly in the cold winter months is tricky, especially when bundled up from head to toe. A warm scarf made from recycled materials in a winter plaid, though? That’s as solid a gifting bet as you’re apt to find.
Upgrade: MR. P. Fringed Houndstooth Wool Scarf ($145)
Everyone should be able to appreciate the small luxuries in life, right? Here’s where this accessory upgrade comes into play by way of an Italian-made wool scarf. The houndstooth pattern is rich and eye-catching, sure to stand out stylishly beneath a tailored navy topcoat on chilly winter days.
Leather Dress Watch
Choice: Breda Visser Square Watch ($90)
With a unique round square face and dressy dial design, Breda’s Visser Watch is an ideal sub-$100 watch for the budding aficionado on a budget. The design of the timepiece is also inspired by abstract-minimalist artist Carel Nicolaas Visser, a nice touch if the style fan in your life happens to love art. The Miyota quartz movement also ensures accuracy at an agreeable price point.
Upgrade: Bulova Classic Black Leather Strap Watch ($146)
There’s something about a square-dial watch we can’t help but love, and we’d bet that the timepiece fan in your life feels the same way. They’ve got timeless charm in terms of design (but accurate functionality in terms of timekeeping itself). This watch also exudes an air of luxury, but at an agreeable price for shoppers and style enthusiasts on a budget. It checks every box in the book if you want a classic watch made with tailored style.
Choice: Lucky Leather Bonneville Jacket ($149.50)
Alongside AllSaints, Lucky Brand puts out some of the most affordable and stylish leather jackets you can pick up. This one is made of genuine leather and is currently 50% off.
Upgrade: Schott Made in USA Unlined Cowhide Cafe Racer ($745)
There is a short list of men's fashion items that will last well beyond your lifetime, and a leather jacket from famed American manufacturer Schott is one of them. Your grandkids will be fighting over it when you're gone – which means you'll get a lifetime of putting it through hell and it'll only look better for it.
Choice: Herschel Heritage Backpack ($64.99)
Good things come in small packages, which is what makes this Herschel backpack all the more impressive. Compact and yet available in three different sizes, it delivers both carrying capacity and reliable looks all the same. We appreciate the Black-and-Tan color combo, and we think anyone who’s into style will agree.
Upgrade: Filson Dryden Backpack ($225)
Heirloom gifts needn’t cost an arm and a leg. While this Filson bag is definitely luxury-leaning, it’s the sort of backpack that will last, quite literally, for years and possibly decades. Filson’s reputation precedes itself, and this durable backpack definitely has that “Wow” factor to impress even the most seasoned style vet.
Choice: Uniqlo Extra Fine Merino Crewneck ($39.99)
There’s a good chance that the fashionable man on your shopping list already knows the affordable menswear wonders churned out by Uniqlo. But a reminder is always welcome, especially by way of this accessible merino wool crewneck. The fact that it’s machine washable should only extend its life, another thing for which to be thankful about this holiday season.
Upgrade: Taylor Stitch Double Knit Sweater ($188)
Sweaters of years gone by, perhaps made with scratchy wool and forced onto you as part of a school uniform, are a thing of the past. Taylor Stitch goes above and beyond, turning the simple crewneck design into something undoubtedly comfortable and memorable (thanks to two soft sides of fabric, all the better for easy wearability).
Choice: Gallaway Leather Portfolio Folder ($24.99)
There’s something to be said for keeping your accessories as stylish and well-made as the rest of your ensemble. Stylish guys know this, and this handsome portfolio folder (sized at 8.5” x 11”) is a reliable gift for anyone, from interns to VPs. Bonus points for the rich leather and low price.
Upgrade: Bellroy A5 Work Folio ($199)
Bellroy’s take on the leather folio is more tech-savvy (it can hold a small tablet and features a phone pocket), yet no less refined. It’s made with environmentally certified leather and even features storage space for a pen and cables. Talk about an incredible EDC gift.
Choice: Line of Trade Summit Flannel Shirt ($65)
What’s not to love about this flannel shirt? The plaid pattern is undeniably winter-friendly, the soft brushed cotton flannel is comfortable on the skin and yet easy to layer underneath a winter jacket, and the fact that it’s made by Bespoke Post is a surefire sign of quality.
Upgrade: Billy Reid Tuscumbia Shirt ($168)
Billy Reid never fails to deliver top-of-the-line menswear, and that extends from outerwear and denim to everyday investments like this cotton plaid shirt. The pattern is memorable and yet still somewhat muted, the fit is modern and the Oxford shirt design is a must-own for every guy who values classic-yet-modern looks.
Choice: Mission Leather Co. Valet Tray ($25)
The days of tossing your keys and wallet on the counter are over (worthwhile advice even when not shopping for a stylish gift). A leather valet tray is the modern man’s way of keeping track of his keys, wallet, phone, glasses… you name it. Three shades of leather give you options to best suit the recipient’s personal style.
Upgrade: Tanner Goods Valet Tray ($85)
The details make the difference, especially in matters of style. If you know a guy who cares about his wardrobe and how things are made, he’ll love this meticulously designed leather valet tray. Better still, it’s made in America with plenty of care and quality.
Choice: Signature by Levi Strauss Co. Trucker Jacket ($35)
Does every guy need a trucker jacket? It’s debatable, but if you’re shopping for someone who prefers casual staples, like thermal henleys and dark jeans, then a trucker jacket is an ideal accompanying layer. It doesn’t hurt that it’s made by Levi’s, a brand that knows a thing or two about denim and trucker jackets.
Upgrade: Flint and Tinder Flannel-Lined Waxed Trucker ($268)
Here’s an upgrade to the classic trucker jacket in more ways than one. As made by Huckberry, this jacket is made from waxed sailcloth for plenty of weather-ready durability. Flannel lining adds to its seasonal warmth, too. Throw in custom hardware and seriously cool color options like Whiskey, and it’s clear you’ve found a splurge-worthy trucker jacket for the fashion fan.
Choice: Emissary Men’s Canvas and Leather Dopp Kit ($14)
Packing toiletries for the road can be so much better than tossing things into a clear plastic bag or a grocery bag. A hard-wearing canvas and leather dopp kit exudes style and offers up a sense of organization to accompany, say, a well-made weekender bag.
Upgrade: Topo Designs Heritage Canvas Dopp Kit ($69)
Topo Designs specializes in adventure-ready gear that also packs quite the punch in terms of style. Horween leather (which will get better the more this dopp kit is used) accents water-repellent cotton canvas. It’s compact enough to pack into a weekender bag or Topo Designs daypack, too.
Choice: SeaVees Wilder Sneakers ($98)
With roots dating back to 1960s California, SeaVees is a tried-and-true option for timeless footwear everyone can appreciate. Although best known for its canvas kicks, SeaVees has blended the crisp appeal of white leather with an eye-catching gum rubber sole. While all-white leather sneakers are a must-have, these are a solid change of pace.
Upgrade: Veja V-12 Leather Sneakers ($145)
When shopping for sneakers for someone, you’ll of course have to know their shoe size (or track it down). All that aside, Veja’s leather sneakers are a step up in quality and style without breaking the bank. They’re distinctive and they’re sharp enough to wear with slim chinos, a cardigan and an Oxford shirt.
Choice: American Trench Retro Stripe Socks ($12.50)
American Trench works with family-owned factories to deliver everything from durable outerwear to these pleasingly vintage-inspired socks. Ideal for wearing with boots and rolled denim, they’re just the right amount of thick, and just the right amount of stylish for casual wear this winter. Once he’s tried American Trench socks, he might never go back.
Upgrade: RoToTo Hybrid Crew Merino Socks ($35)
When are socks more than just socks? When they’re made in Japan using everything from merino wool (breathable and moisture-wicking) to nylon for added durability. The crisp navy color means you can wear them with dress trousers and leather shoes, but the fabric’s functionality means they’re well-suited to be worn with lace-up boots anytime the wearer gets the urge.
The Everyday Carry Pen
Choice: BASTION Bolt Action Pen ($43.99)
The man on the go needs a pen he can easily access at all times, and it’s all the better if that pen is a high-quality piece that’s efficient in terms of design and functionality. The bolt-action design makes it easy to prep this pen for writing on the go, so keep that notebook at the ready.
Upgrade: Dango Products Titanium Mini Pen ($85)
No more fumbling around in a console or bag for a pen. This incredibly well-crafted titanium pen is nicely sized to fit in the pocket of a jacket or work shirt, with a design that stands up to repeated used without running out ink. That’s a style upgrade he can appreciate.
Choice: Amazon Essentials Shawl Cardigan ($25)
A shawl cardigan is many things at once: A style swerve from a traditional crewneck or V-neck sweater, a piece that can be dressed up and a cozy layer to wear at home. This Amazon shawl cardigan is all of those things at once, with a ribbed knit that delivers winter warmth when worn over a long-sleeve T-shirt or a stretch dress shirt.
Upgrade: Buck Mason Herdmsan Shawl Cardigan ($225)
Whether or not the stylish guy in your life has tried Buck Mason before, this rugged shawl cardigan is an expert pick-up. It’s the kind of thick-knit sweater you’d find on a mood board alongside old-school fashion icons, yet it’s just as easily wearable in 2021 as in decades gone by. The ribbed design makes it perfect for layering over henleys and flannels.
Choice: Huckberry Cruisers ($35)
At first glance, you might think a pair of sub-$40 sunglasses are going to prove flimsy or cheap. However, that’s decidedly not the case with this pair of shades from Huckberry. They’re designed to withstand drops, bumps and repeated wear. The fact that they look great on just about anyone is a big-time bonus.
Upgrade: Maui Jim Cruzem Sunglasses ($250)
Trust the pros at Maui Jim to make some of the best sunglasses on the market. These will come in mighty handy against either blindingly bright winter sun and snow, or better still, on a tropical vacation (short-sleeve printed shirt sold separately).
Choice: Goodthreads Crewneck Cotton T-Shirt ($12.90)
When paired up with other items, a T-shirt makes a solid addition to an entire “gifted ensemble,” and it’s hard to go wrong with a soft cotton tee you can layer with just about anything. Whether he favors T-shirts for work or play, whether he pairs up a tee with a cotton blazer or underneath a flannel shirt, it’s a reliable style move. You can never have too many comfortable T-shirts, right?
Upgrade: Knickerbocker T-Shirt ($48)
This USA-made T-shirt might look simple on the surface, but look more closely. It’s made in Portugal from a just-right cotton fabric that’s neither too heavy nor too light. The collar is also sewn onto the top of the T-shirt, rather than underneath the T-shirt. This adds another touch of durability and vintage style unlike anything in the wearer’s T-shirt drawer right now.
Choice: JBL Tune True Wireless Earbuds ($70)
JBL prioritizes both utilitarian performance and a premium listening experience alongside accessible design. Another benefit to wireless earbuds? They won’t distract from a winter style ensemble with pesky cords. They’re as streamlined and smooth as it gets for the audio fan.
Upgrade: Master & Dynamic MW08 Bluetooth Headphones ($299)
There are the standard-issue cord earbuds delivered with every iPhone, and then there are these truly exceptional, professional-quality Bluetooth headphones. Consider gifting these to the guy who absolutely loves studio-level sound in a small package. Noise-cancelling functionality and talk-on-the-go capability are just two features to love.
Choice: Victrola Houston Bluetooth Radio Speaker ($60)
Give the gift of great sound, all packaged in a pleasingly retro design. This is the kind of Bluetooth speaker to add some throwback flair to a home office or den, and it comes complete with FM radio accessibility, too. All that’s missing is a roaring fire and some holiday tunes.
Upgrade: Tivoli Audio Revive ($249.99)
Part crystal-clear Bluetooth speaker, part lamp and part design centerpiece, this Bluetooth speaker is next-level in every facet. The audio quality is nuanced enough to please every audiophile, and it even features a wireless phone charger. The tech and design-obsessed will love what Tivoli Audio serves up here (and they’ll love you for gifting it to ‘em).