The guys on your list are the hardest to shop for. We all know it, yet we all try to come up with a special gift we think they’ll love, but that they end up just tossing to the back of the closet only to be pulled out when we ask, “what happened to that cashmere sweater I bought you last year for Hanukkah?” And it magically appears.

As hard as we try, some guys just won’t change—they’ll always prefer a six pack of beer to a new tie and matching pocket square. The safe answer? Send him a Hanukkah gift card and let him choose a gift he’ll keep on the front lines of his closet, or an experience that caters to his—rather than your—tastes.

For the lazy shopper.

Just because you vowed to never force him into a floral-printed button down ever again (after last year’s Great Hanukkah Debacle of 2013) doesn’t mean you can’t give him a gentle nudge in the right direction toward style. ZipFit Denim is an online men’s shop that uses a special algorithm to find your guy’s perfectly fitted denim—all without a single trip to the fitting room. All he has to do is fill out a super easy survey. It’s seriously that simple, especially with a gift card. Maybe you can even talk him into a checkered shirt to go with jeans.


For the man maven.

Even if the guy in your life—be it your brother, husband, or debonaire dad—enjoys a good, old-fashioned trip to the shop for his clothes, he’s probably a lot pickier than you’d prefer. Chicago men’s boutique MEYVN (pronounced “maven”—get it?) is known for their love of leather, sneakers, and hats in every variety. It’s nearly impossible to steer your guy in the wrong direction with a Hanukkah gift card to MEYVN.


For the beer-ded one.

He doesn’t really care about fashion and only goes shopping to make you happy (and to get you off his back), but he certainly enjoys a cold brew, even in the Polar Vortex part 2 temps. With a Hanukkah gift card to Beermiscuous—a Chicago beer café—he can sip on craft beer (or several) while finishing up some work. And you can enjoy your favorite brew while online shopping. Just pick up some takeout from your favorite neighborhood eatery and head to Beermiscuous where the two of you can have a proper post-holiday date to unwind. Consider this one a gift to yourself, as well.


For the triathlon buff (who’s seriously buff).

He’s been down in the dumps ever since the first snowfall, and it’s all because he can no longer stick to his all-day, everyday cycling, running, and swimming schedule. So sad. To give him a little bit of hope that the sun will once again shine as bright as your Hanukkah lights or the candles on your menorah, send him a gift card to Live Grit—Chicago’s only laid-back triathlon shop. He can start stocking up on next year’s gear, from the wetsuit, to a new pair of running sneaks, to a new bike (if you’re really generous with the gift card). We have no doubt this one will finally draw a smile from that exercise-deprived face.


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