Dennis Todisco on HBO Max’s ‘The Hype,’ His New Role at Instagram & the Hottest Fall Sneaker and Streetwear Trends

Dennis Todisco launched @Outfitgrid on Instagram almost 10 years ago, a beloved and highly influential account for the fashion-focused. Today, he is using his expertise to help Instagram develop relationships with needle movers in sneakers and streetwear.

The social media platform tapped Todisco to fill its sneakers and streetwear role in November 2020, and in the months since has helped improve its Checkout and Drops functions, and also worked on several product releases, most notably apparel from Fear of God.

This week, the spotlight has been placed on Todisco’s expertise in several ways. For starters, he appeared on the HBO Max streetwear competition series “The Hype,” which arrived on the platform today. And his insights were included in Instagram Insider, a shoppable trend report, which also dropped today.

Below, Todisco offers a look into his role at Instagram, the legacy of @Outfitgrid and talks about the streetwear trends and sneakers people should expect to dominate this fall.

How did you land at Instagram as its head of streetwear and sneaker partnerships?

Dennis Todisco: “[Instagram director of fashion partnerships] Eva Chen realized that this was a fast-growing segment on Instagram, put the word out and I connected through a former coworker of mine, Fadia Kader. She reached out to me saying, ‘Eva was thinking about creating this role, would you be interested?’ This was a while ago, maybe March 2020. Once the role was created, I went through the formal process of applying. My job here is overseeing all the streetwear and sneaker relationships. I work very closely with brands, designers, retailers to help them tell their stories on Instagram and grow their businesses. Very excited to be on this team, on fashion partnerships under Eva Chen, working with the best partners in the world. We have such an incredible presence on Instagram as it pertains to sneakers and streetwear, and I’m very fortunate and happy to be in this role and help unlock new opportunities for these partners and friends I’ve made over the last few decades.”

Since arriving at Instagram, what have you worked on?

DT: “Some of the biggest things were on the product side and behind the scenes. When I came in, obviously there wasn’t anybody in this role doing what I’m doing and nobody had that perspective from a streetwear or sneaker partners’ frame of mind. What I was able to do is advocate for my brands, my designers that I work with and help them shape the product in a way that’s beneficial for them. For example, with Checkout we’ve made some big improvements and launched some new features. And Drops is something that leans into the sneaker and streetwear space. It’s a way for brands to launch coveted product on the site with a notification opt-in, so if you’re a consumer and you follow your favorite brand and you see they have something cool coming up and it’s a drop, you can click ‘notify me’ and then you’ll get a push notification sent to your phone 24 hours and 15 minutes before it launches. We’ve done some pretty cool drops so far. We’ve worked with Fear of God on a couple of drops around different moments — we did a drop raising funds for the Gianna Floyd Foundation, we also did one during the election with Kamala Harris, a Kamala Harris x Fear of God hoodie, we’ve done several launches with The Hundreds, we launched Drake’s Better World Fragrance House.”

What are some of the trends in streetwear people can expect to see in the fall?

DT: “There are several trends that are happening that I think are interesting. We’re seeing a lot of vintage treatments, pre-distressed. We have some upcoming projects like, of course, Virgil [Abloh’s] Jordan 2 is coming out in the near future, which is very distressed. Past releases like Union [Air Jordan] 4s or A Ma Maniere 3s or Travis [Scott] x Fragment 1s with off-white, pre-distressed soles are really hitting right now. And we’re seeing a lot of Instagram creators also taking new pairs and applying vintage treatments. They’ve been doing some really cool Reels content and Instagram content showing the process around how they create vintage treatments. And we’re seeing a lot of great outdoor trail technical footwear. Nike has been killing it with ACG, like the Olivia Kim Air Mowabb, the No Cover collection is really a standout, Salomon is really picking up as well. It’s that return to people wanting to go outside again.”

The outdoors has never really left fashion, it’s just had its peaks and valleys. What is the role of the outdoors in fashion today?

DT: “To your point, there are mainstays in fashion, like hiking and skateboarding. It always exists. People who love skateboarding, it’s not a trend, it’s a lifestyle. It’s similar to outdoor trail running technical footwear. But we do have pockets in this wave of trends where all of a sudden people are very focused on [Nike] Dunks, for example. In this moment, people are starting to get very focused on technical or trail footwear. I feel it’s in the spotlight right now. The nice thing about that is it transcends a trend. If you are invested in this, it’s something that is going to be cool after because it’s something that’s been cool before. As long as you’re about it, you can’t lose.”

How, if at all, has the ongoing work-from-home situation impacted fall trends?

DT: “It’s impacted them a lot. We’ve seen so many footwear silhouettes that are unexpected have a huge rise. A few examples that come to mind are Crocs, Birkenstocks — the Boston in particular. People are definitely gravitating toward slip-on and comfort. But I’m also seeing that evolve into something different with the preppier styles as well, with loafers. There are several brands that are doing well with that, like Blackstock & Weber, Gucci and Collegium, creating really cool loafers. That slip-on feeling is still there, but it’s elevated in a more dressed-up style.”

Who are some of the people and brands in footwear and fashion who are needle-movers today?

DT: “Something that’s happening is this big shift toward the new creative director. We’re seeing people who were one-time collaborators now becoming mainstream fixtures at these brands. People like Teddy Santis from Aimé Leon Dore as the new creative director of New Balance Made in the USA or Kerby Jean-Raymond of Pyer Moss becoming the global creative director of Reebok, Brendon Babenzien of Noah becoming the creative director of J.Crew. We’re seeing the streetwear or streetwear-adjacent creative directors or founders becoming these mainstream creative directors, and it’s a really smart move by the brands because they’re able to tap into that industry expertise and skill.”

What is the legacy of @Outfitgrid?

DT: “It is such an incredible, vibrant community. People are coming together from around the globe over this simple idea of sharing your style without micro judgments. I hope to leave a legacy of people who were able to share ideas and meet in a positive and welcoming environment that allowed them to discover new styles, new trends to level up how they dress. It’s been really positive and very awesome to see people come together. People have been doing meet-ups for years now, literally hanging out together in different cities, which is pretty incredible for just a simple hashtag.”

For those who haven’t watched yet, what can people expect from your appearance on the HBO Max “The Hype” finale?

DT: “I actually love the show, it’s amazing. There are some really cool and very moving storylines, especially on episodes four, five and six. My appearance on ‘The Hype,’ I don’t want to give away too much, but I come on to the show and talk to the two finalists and give them some pointers on how they can bring their collections to life on Instagram. I haven’t seen the footage yet, so I don’t know exactly what to expect. It’s awesome because it shines a spotlight on this subculture that’s now obviously bigger than any subculture. There are so many talented people that exist within the space of fashion and footwear, and it’s awesome to see people get recognized and grow. All of the contestants that participated in the show will hopefully have new opportunities coming out of this and new growth — and we want to see that.”

What makes the “Instagram Insider” shoppable trend report such a valuable resource? 

DT: “We’re trying to just uncover the emerging trends that are happening on the platform, give people inspiration, help brands and marketers who look at what’s happening on Instagram at a trend level, which is super insightful and valuable. It’s also an opportunity to highlight the amazing brands and the amazing content creation that happens on the platform every day.”

Did anything outside of the world of streetwear stand out to you from the report?

DT: “One of the trends that I thought was pretty interesting was this trend of ‘Come On, Get Happy’ — kind of building off of this trend of bright colors, bright design, over-the-top silhouettes, kitschy prints, upbeat motifs. I feel like it’s very relevant for streetwear as well. People have been wearing the same sweatpants and slippers, and it’s been boring. It’s time now to go back outside and wear something fun, get dressed up, and that’s super spot-on with how we’re feeling.”

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