The Ultimate Streetwear Holiday Gift Guide For 2020

Shopping for a hypebeast? Yeah, we know, it can be tough. Streetwear is prohibitively expensive and the people who wear it are infuriatingly picky. Trust us, we put together a weekly streetwear roundup every single week. That means we literally are that picky person who looks out into an endless sea of releases and decides which drops are worth obsessing over.

It’s exhausting, but that’s the job. Thank your lucky stars that all you have to do is sit back, scroll, and decide what you want to spend money on.

Today’s streetwear scrolling comes in the form of our streetwear gift guide for 2020. You’re sure to see some of the dopest streetwear brands operating at the top of their respective games plus some surprises and indie outfits making noise. If you’re looking for something more sneaker focused, be sure to hit up our Sneakerhead Gift Guide for even more streetwear goodness.

Part 1: Apparel

Shop Supreme’s Fall/Winter 2020 Collection


Price: Varies

Believe it or not Supreme is still by far the most popular streetwear label operating right now, and if you have only a shallow understanding of the brand then that might lead you to believe it’s prohibitively expensive and impossible to find. That’s only the case with very specific pieces and collaborations, but the brand is constantly refreshing its stock with new drops.

Right now, Supreme is deep into their Fall/Winter 2020 collection, which means if you’re looking for winter staples like down parkas, hoodies, crew neck sweaters, and coats, Supreme is well supplied. Hit up their official webstore and find a fit that works for whoever you’re buying for.

Shop Supreme here.

Shop Palace’s Ultimo Collection


Price: Varies

If you’re looking for a brand with less name recognition (and a smaller general price tag) that’s just as respected as Supreme by hardcore streetwear fanatics look no further than Palace. Palace is pretty much a Supreme Jr. (though me saying so will anger both Palace and Supreme fans). The UK based skatewear brand is in the midst of their extensive Ultimo Collection, a giant winter-focused collection of streetwear basics like coats, jackets, sweaters, pants, and hats.

If you’re shopping for a bucket hat fanatic, this is your company.

Shop Palace here.

Fear of God Fall 2021 Collection

Fear of God

Price: Varies

If the streetwear obsessed person in your life is a little more fashion-forward than the basics offered at places like Supreme and Palace, they’ll likely appreciate something from Fear of God’s 2021 line. Since the brand’s inception, Jerry Lorenzo’s Fear of God label has been injecting elegance into the world of streetwear, producing fits that look luxurious but wear comfortably.

The brand also has a line dubbed “Essentials” which is a bit more athleisure focused with an emphasis on clean and minimal designs.

Shop Fear of God here.

Travis Scott Cactus Jack Merch


Price: Varies

No name aside from Virgil Abloh makes modern streetwear enthusiasts lose their shit quite like Travis Scott. Through his Cactus Jack label, Scott has dropped several pieces of merch this year, from t-shirts to sweaters to sneakers to hats to hoodies. The dude has even made face masks.

Grabbing the streetwear-obsessed person in your life some Cactus Jack merch will be a sweet addition to their collection, whether they are big Travis Scott fans or not. Sadly, you’re going to have to get it on the aftermarket.

Shop Travis Scott Merch at StockX.

Editor’s Pick — Eddie Bauer JJJJound Skyliner Jacket


Price: $299

Eddie Bauer isn’t overly associated with streetwear, but… maybe it should be? This classic puffer in military green hits the design-meets-simplicity sweet spot. You could see it coming out of Palace in 2020 but you could also envision Paul Newman wearing the thing in 1970.

So often, these quilted puffers — even from the big brands — suffer from one stupid design thing that mangles the whole operation. They make the quilt sections too small or the fit is weird or the collar is strange or whatever. This piece from Bauer’s JJJJound line makes zero mistakes.

It wears well, looks modern, and feels classic. Everyone needs more clothes that can pull that high-wire act off.

Buy it here.

Editor’s Pick — Free & Easy Worldwide LS Tee

Free & Easy
Free & Easy

Price: $68

Free & Easy is a brand that uses the logo art from a 70s surf film made by a pal of mine, which, in turn, takes its title from the book I wrote my master’s thesis on.

So… yes, it’s my shit.

And while I practically never wear shirts that have big mantras on them, this one fits for 2020 and beyond:

“Don’t trip. Relax and enjoy life.”

God, how hard do we all need that right now? Plus it’s got a bunch of globes that feel reminiscent of the old Pan Am logos. If whoever you’re buying for right now is dreaming of travel as much as I am lately, they’ll love this.

Buy it here.

Editor’s Pick — Parks Project Olympic’s Greatest Hits Tee


Price: $38

Are you up on Parks Project and how freaking cool they are? They literally create apparel that helps fund our National Parks. That work was more important than ever in 2020, with revenues down and the president constantly attacking our shared outdoor spaces.

But beyond its general altruism, Parks Project has awesome design sense. Their NatGeo collabs are historic, but you definitely shouldn’t sleep on their in-house designs. This ringer shirt for Olympic National Park is a great example — a cruisy, album cover-inspired little throwback design for your friend who surfs cold water breaks and drinks coffee out of enamel mugs. (Parks Project also makes enamel mugs, but the last release sold out so freaking fast you would’ve thought it was a Supreme x Off-White collab.)

If you dig this shirt, get it. But my bigger encouragement is that you spend time with this whole line. They’re doing some fantastic stuff and benefitting National Parks in the process.

Buy it here.

Editor’s Pick — Dim Mak x Bruce Lee Dragon Hoodie


Price: $75

Dim Mak, Steve Aoki’s merch and streetwear line, is on our “brands we love” list, but you really don’t have to love the brand to want this hoodie. It’s Bruce Lee. Who doesn’t want to rep Bruce Lee?

I could wax philosophic a little longer here, but probably don’t need to. There are a million hoodies on this planet. Not all of them have martial arts legend, cinematic hero, tragic figure, and Tarantino muse Bruce Lee on the front. This one does.

Someone you know would be beyond hyped about this.

Buy it here.

Editor’s Pick — Todd Snyder Midnight Pocket Sweatshirt, Mustard

Todd Snyder

Price: $98

Okay, we’re taking it back to the old school again. Back to Paul Newman. This sweatshirt is a classic. It’s also $100. As the owner of three of these, let me tell you though: It’s flat-out made better than other sweatshirts. The quality is impeccable — you feel it in the stitching, the sleeves, the neck… it probably won’t pill up for 100 years.

It’s slim-fitting and shockingly soft. Makes you feel rich in the “I can afford to look casual in this incredibly made sweatshirt” way, instead of the “I overpaid for a brand name” way.

Plus that old Champion logo work that Todd Snyder licensed? Fire.

Personally speaking, I wear this all the time with jeans and get endless compliments. It’s one of those exceedingly rare casual pieces that have a legitimate chance to get better with age and last long enough to be someone’s cool thrift store find in 20 years. I can’t overstate how uncommon that is in modern streetwear.

Buy it here.

Part 2: Sneakers

For The Runner — Adidas Performance Ultra 4D x SNS Green Teatime


Price: $249

Adidas 4D running sneakers have some of the most cutting edge performance-driven sneaker technology out there right now, when the sneaker first dropped a single pair would retail for $400. Those days are thankfully over, and now the silhouette is receiving some of its best colorways to date like this Green Teatime iteration released as a collaboration with sneaker store SneakersnStuff.

Dipped in a colorway of mint green on green with core black, this unisex runner features Adidas’ forward-thinking 4D midsole with an all Primeknit upper and dope-as-hell name. Which sneakerheads care about.

Shop the sneaker at SneakersnStuff or StockX.

For The B-Ball Fanatic — Nike Jordan 4 Retro Fire Red


Price: $230+

Amongst Jordan fans, you’ll hear these terms thrown around a lot: Black Toe, BRED, OG Chicago, and Fire Red. They’re four of the brand’s most legendary colorways and Nike just dropped the Jordan 4 in Fire Red a couple of weeks back, the first time the colorway has been refreshed since 1989.

Why are sneakerheads going crazy for a color combination from 31 years ago? Because they’re huge nerds. Us that to your advantage — grab someone you love a pair of 4s in Fire Red and you’ll be an absolute hero.

Pick up the sneaker at StockX or select Nike retailers.

For The Fashion-Obsessed — Nike Off-White Sneakers


Price: Varies

For the most fashion-obsessed streetwear fanatic hit up StockX search “Nike Off-White” and find the sneaker that best fits their vibe. Off-White is THE brand in streetwear, it has the most devoted fan base, and the biggest haters, a true hallmark of streetwear success. Most pairs will run you in the $200 range and some pairs will make you lose faith in humanity, like this pair of Woman’s sized Jordan 4 Off-White Sails, which easily sell for above a grand.

Sorry for having an entry this exclusive/ expensive but… they are dope.

Shop Off-White sneakers at StockX.

Editor’s Pick — SeaVees Maslon Desert Boot


Price: $130

Are they sneakers?

Not technically. But they are cool as hell and a vital item in your whole style look. Classic desert boots are a must for anyone who balances the surf-skate-music cultures with adventure and exploration.

To put it another way, these are the sorts of boots that a cool sculptor, your dirtbike riding dirtbag friend, a tatted-up chef, and a hipster-ass musician who practices vertical hydroponic gardening on the side would all rock. If someone you’re shopping for hits those notes, these are fresh (non-sneaker) kicks for them.

Buy them here.

Part 3: Accessories

Jason Markk Shoe Cleaning Gift Box


Price: $59

SneakersnStuff sells a Jason Markk sneaker cleaning bundle that will give your sneaker loving streetwear fanatic everything they need to keep their kicks looking fresh. The bundle features a 4 oz bottle of shoe cleaner, Repel spray to keep new sneakers stain-free, 6 quick wipes for spot stains, two different brushes, and a microfiber towel for a final rub down.

Buy it at Sneakersnstuff.

Casio G-Shock Watch


Price: (Aftermarket prices vary $100-$250)

A Casio G-Shock is a great watch option for someone who wants the accessorization of a watch without wanting to make a statement about their wealth. They’re relatively inexpensive, with hundreds upon hundreds of different designs, and they pretty much last forever. People lose G-shocks, sell them, break them, but very few ditch their G-Shock because the battery died.

Find one that reflects the personality of the person you’re buying for, or check out which watches are trending on aftermarket sites like StockX, a lot of the dopest limited designs end up there.

Check out StockX or the Casio Webstore.

Telfar Tote Bag


Price: $200-$300 on the Aftermarket

Telfar has exploded in popularity, primarily thanks to their genius marketing that positions their minimalistic tote bags as a for anyone accessory. Nothing ruins a fit like keeping a bunch of junk in your pocket, it’s why fanny packs are back in, and nothing pulls together an outfit like a Telfar Tote which sports a simple one-color design that can both complement or contrast the colors you’re working with.

If it’s cool enough for Issa Rae, AOC, Solange, Dua Lipa, and A$Ap Ferg, it’s cool enough for anyone in your life.

Telfar bags are almost always sold out but feel free to check the official Telfar webstore, or you can just hit up StockX.

Editor’s Pick — Parks Project Trail Crew Beanie


Price: $28

Parks Project doubles up in 2020!

Okay, we try not to feature brands twice on the same guide but these beanies…

So simple. So cool.

Logos only work if they pledge allegiance to something other than capitalism. Flossing a Parks Project logo on your head does exactly that.

Buy it here.

Editor’s Pick — Tejesta Geronimo Havana Sunglasses


Price: $245

Tejesta is a fresh eyewear brand in both senses of the word — fly and new. The sunglass upstart remixes Indigenous geometric designs and iconography but does it in the right way. One of the founders is an enrolled member of the Tewa Tribe, the name highlights the Tequesta people of Biscane Bay, and the company is launching an initiative for financially providing opportunities for Indigenous people in 2021.

Once you know that this is a brand that isn’t just appropriating Indigenous culture, you’re able to sit back and appreciate how freaking fly these shades are. Seriously, all the designs look fresh. This pair, which are reminiscent of Ray-Ban Wayfarers but with a more stylized, less plastic-y feel, are my favorites.

The quality, the case, the look, the ethics of the brand — these sunglasses represent the energy the people you love want to bring into 2021.

Buy it here.