Giving gifts is both art and science. Between the truly thoughtful and the iTunes gift card lie the casualties of Chirstmas Past: scented candles, TV box sets, and gasp novelty coffee mugs. Despite the giver’s best intentions, pure uncertainty (and often, a healthy dose of procrastination) creates the conditions for cliché.

Instead, there’s hope – rather than add yet another voice to the white noise of “Best Of 2016” lists, I’ve compiled my picks across many categories into a gifting resource to help you choose the perfect present. With this guide, you’ll have a wide range of options perfect for the man on your list, no matter his interests. No ugly sweater needed.



2016 was a hallmark year for sneakers. While most of the “hyped” pairs will be impossible to reliably find in stock, there are still dozens of popular models in colorways well worth your dollar. The adidas Ultra Boost 3.0, releasing December 8, 2016 in a wide range of colors, is my top choice – as both high performance runner and street style icon, it simply covers all the bases.  

If you’re looking for a bonafide casual sneaker for someone who leans towards minimalist style, choose the Greats Royale in Vintage Red. The cream Margom sole and red suede heel tab liven up this precise silhouette, and while it lacks the tech of the Ultra Boost, the Royale flourishes in the casual context it was designed for. After all, it’s a Made in Italy luxury leather sneaker priced below $200 – compared to Common Projects, the Royale is a steal and a half.

That being said, this is winter: while sneakers are welcome all four seasons, giving a good pair of boots scores bonus points as soon as the temperature drops. My recommendation: the Thorogood American Heritage 6” Moc Toe. It’s chunky Vibram outsole and sturdy all-leather construction makes it a champion in all conditions. Plus, for a sub-$200 boot, the fact that it’s Goodyear welted (a special – and expensive - method of shoe construction that is both durable and prime for resoling) means both present value and future lifespan. Pretty good for some dead cows.



In my opinion, socks are the perfect example of the “holiday gift binary”: you will either love a pair you’re given (and wear them with joy), or hate them (and wear them only when their giver visits). Even better, as one of the few truly universal gift categories, socks will always be a part of Christmas. Despite their utility, if you give bad socks – or worse, 10 pairs of bad socks jammed into a “Value-Pak” – the effect of your gift will be lost in the owner’s ambivalence.

Thankfully, there’s a simple solution: just give great socks.

If you’re looking for stylish socks on a budget, check out selections from Mossimo, Target’s in-house fashion brand. Their wide and irreverent selection covers… well, just about everything.

For a more design-oriented take on socks, I highly recommend the Japanese brand Anonymous Ism. Their Patchwork Socks (below) are one of the most iconic men’s accessories of the decade, and provide subtle visual intrigue to any outfit. However, if the words “design” and “Japanese” didn’t tip you off already, it’s worth mentioning that Anonymous Ism socks don’t come cheap. No Value Pakking here.



Speaking of holiday hallmarks, we come to books. Even in an age of e-readers, it is my firm opinion that giving physical books you enjoy remains one of the truest ways to give – and receive – something of significance.

As the giver, you bestow a token of yourself to someone who you believe will enjoy the topic. In turn, you provide them insight into both the book’s subject and your own values.  

As the receiver, you earn a window into the world. The reading process – scanning, digesting, thinking, then applying – grants you the rare joy of a truly personal experience that one can apply past just the walls of their internal monologue. Books shape your words, your choices, and your interactions. Knowing that someone thought so highly of you as to present a part of their shape for your benefit, then, may just be one of the truest gifts a human being can receive.

My favorite books of this year are diverse in topic, yet all wildly enjoyable. Enjoy.

Shoe Dog by Phil Knight – the autobiography of Nike co-founder Phil Knight is everything you wouldn’t expect from the man behind one of the world’s most audacious brands: humble, shy, reflective, and deeply personal. Most corporate memoirs read like the Arc de Triomphe with an IPO. Instead, Shoe Dog is honest: the story of Nike is one of mistakes and resilience, not rose-tinted glory. I finished this book on a hill in Central Park just before going on a run this June. It is one of my fonder memories.

Seveneves by Neal Stephenson – the only piece of media that could have made orbital mechanics engaging. Stephenson’s latest tome is a 700-page narrative in three parts. While it is ostensibly sci-fi, Seveneves is so much more than space travel and shiny technology. At its core, Seveneves is a story about how we, as humans, deal with progress in the face of overwhelming adversity. By page 300, the world has ended. And that’s just the beginning. If you've got a long flight home for Christmas, there is no better companion.

Type Matters by Jim Williams – the one text everyone who wants to make an impact should read. Type Matters is both lesson plan and case-in-point rolled into one beautiful primer. In less than 200 pages, Williams explains the tenants of typography and design, while demonstrating the effect that proper typesetting has on communication by spelling out how specific pages and messages are influenced by the techniques on display. If Powerpoint is part of your job, buy this book and do your best to absorb it. The success will come soon after.



The ultimate gifting taboo. To keep things short, I’m not actually suggesting you buy clothes for someone: one’s decision to wear clothing of any type is so deeply personal that gifting it creates more uncomfortable politics (“Wear the sweater Grandma got you”) than it does holiday cheer. And that's not even getting into the delicate matter of sizing.

Instead, I’m suggesting you consider gift cards (either physical or digital) to the following exceptional brands and retailers – each has quality product, diverse selection, and worst comes to worst, a comprehensive return policy.

(listed in order of price, low to high)

Uniqlo - Japanese design influences high-quality, stylish basics

J. Crew - American prepwear meets a modern aesthetic

Bonobos - Biz-caz outfitter with innovative e-commerce model

Today Clothing - Japanese/Americana multibrand retailer 

Notre Chicago - The world's best menswear retailer (pictured above)



No one ever outgrows toys – the toys just get more expensive. While I’d love to recommend a drone or a hoverboard, there are many more *ahem* applicable toys out there, ones that will improve your life without catching on fire, either. First up, for the man who has everything: an Adobe Creative Cloud subscription. At $20/month for students, the Creative Cloud is a no-brainer for anyone who works in a remotely creative capacity, or even aspires to. Unlimited access to the latest versions of Photoshop, Illustrator, and InDesign is a gift that keeps on giving.

Next up, for the aspiring iPhone documentarian, give a beginner-level digital camera. Entry-level mirrorless options like the Canon EOS M10 provide a welcome jump over phone cameras in a lightweight, intuitive product that undercuts most beginner DSLR’s.

Finally, give the gift of gear with a stylish technical backpack. Selections like Cote et Ciel’s Isar Pack (below) or DYNE’s Giga Knit Backpack are a cut above the typical “black North Face backpack,” and are just as usable for day-to-day tasks. Bringing a hiking pack around campus because you climbing once a year is like wearing ski boots all summer because of your Christmas vacation – overkill at the expense of some truly wonderful alternatives. Even better: backpacks are one size fits all.


Was this Gift Guide helpful? Did these suggestions point you in the right direction? Let me know on Facebook or by reaching out in the comments below.



AS RAKESTRAW | The personal site of Alex Rakestraw.