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Ask the Strategist: Would You Please, Please Do a Roundup of Cool Olympics Merch?

Photo: retailer

In our advice column, “Ask the Strategist,” we take your most burning shopping questions and survey friends, call up experts, and draw on our own personal experience to answer them. If you have an online-shopping question of your own, please send it to with the subject “Ask the Strategist.” We’re here to help.

Would you please, please do a roundup of cool Olympics merch? We always go Games crazy and want to represent with more than the official stuff and the same Ralph Lauren shirt again.  There must be some fun stuff out there!

You’re right. Finding cool Olympics merchandise is no easy feat. With Nike and Ralph Lauren the official outfitters of the Games, they dominate the space. While some of it’s classic and gets the point across (and official merchandise has that collector’s item appeal), there are other places to look if that’s not quite your style. Pro tip: Searching whatever sport you’re most excited to watch or the athlete you’re rooting for is one way to find some unique items. As for generic Olympics gear, we’ve rounded up the best of the official, traditional, and unexpected merchandise out there. The Games don’t officially start until July 23, so we anticipate even cooler stuff to hit the market in the coming weeks. But the list below will start you off in the right direction.

[Editor’s Note: Some of this gear still reflects the 2020 date, as the official name of the Games is Olympic and Paralympic Games Tokyo 2020, despite its being postponed to 2021.]

I know you said you weren’t interested in the official merch, but trust us, some of it’s worth looking into. This T-shirt repping the USA surfing team moves away from the traditional red, white, and blue color palette and throws in some splashes of yellow and pink. It’s not obviously Olympics merch until you see the rings and American flag patch on the shoulder. If you’re into collecting, not only is this shirt from the official team shop but it also commemorates the first year surfing will be a sport at the Olympics, making it a special buy.

Skateboarding also makes its Olympic debut this year, and the merch is definitely cool enough to mark that occasion. This T-shirt has an ’80s font and a checked backdrop. It’s something you’ll want to wear well after the Olympics are over.

Photo: retailer

The Ralph Lauren stuff can get a little cheugy, but among the polos and American-flag designs, there are a couple of things that look slightly cooler. This tee incorporates a little bit of everything: You’ve got the official logo of the U.S. Olympic team on the sleeve and the Stars and Stripes shield for a little Americana, but Tokyo in huge letters and athletes in motion take center stage here.

Photo: retailer

Nike’s got a number of things in the team shop, but for something Nike that’s a little less on the nose, these red, white, and blue Air Maxes are more than just a patriotic colorway. According to the description, the 97s were inspired by Japanese bullet trains, and the American colorway makes them perfect for cheering on Team USA at the Tokyo Olympics.

Photo: retailer

Ben Sherman is one of the official supporters of Team Great Britain, but its merch is too chic not to include. Thankfully, it has the same colors as the U.S., so as long as you don’t get any of the items with the Union Jack emblazoned on it, no one will know you’re a traitor. This knit polo is particularly attractive and can take you straight from work to an Olympics party. It’s perfect if your main goal is to look patriotic without a lot of busy graphics.

If you don’t mind a graphic tee, this Tokyo stamp design is pretty interesting. If you’re rooting for the home team, just don’t let people get close enough to see the “Team GB” hiding in the print.

Rowing Blazers is the official clothing supplier of the U.S. rowing and rugby teams, so the brand has an official collection of Olympics merch, but we think this rugby from its regular collection is even cooler for the Games. You can pay homage to the host country with this vintage rugby repping Japan’s national rugby team, the Cherry Blossoms.

Photo: retailer

This tee is textbook business in the front, party in the back. The front just reads “Skateboard,” while the back has this fresh graphic. In addition to an abstract skateboarder, there are the Olympic rings, and “Tokyo 2020” is crossed out to reflect the 2021 rescheduled date.