Since 2012, Dennis Todisco's Outfitgrid has become a self-contained community of style enthusiasts, carefully laying out their fits in knolled formations that would make Tom Sachs beam with pride. Since then, it's become a daily flexfest for people around the globe, where Todisco reposts his favorite one from the past 24 hours.

Given how much men's style has become a competition unto itself, it's no wonder why his following keeps growing. He has two basic rules for how he picks the winner of the day. The first is to bring a sense of style into the fit, instead of just showing the latest things you've copped.

“When people are able to incorporate their personality into their fits, and show pieces that really speak to them, that's more impressive to me. Not necessarily just: ‘I'm a mannequin in the store, here's a head-to-toe Dior fit,’” he says. “The other thing that's a basic qualification is having a clean shot. If the clothes are out of frame, hard to see, or in bad lighting, that takes it out of the running.”

At first, Outfitgrid catered to the sneaker and streetwear set — featuring plenty of box logos, BAPE camo, and more Swooshes than Drake's latest music video. But it's since evolved along with sneakerheads' collective sense of style, featuring high fashion brands alongside streetwear and sportswear labels.

That's why we linked up with Todisco to see how he'd interpret another rapidly-growing digital fashion subculture: the archivist. Pulling a few collectible pieces from Artifact New York, we sent a few runway duds to the man behind Outfitgrid to get his take on the gear and see how he'd put it together.

What's more, sneakerheads and fashion heads now have something else to bond over: if retros are a good thing for the hobby. Certainly, dudes now seeing the market value of 1985 Jordan 1s and mid-2000s Nike Dunk SBs can commiserate with people trying to track down Helmut Lang's Re-Issue pieces and Raf Simons' upcoming re-editions.

“I appreciate both sides of the coin. A designer label might want give people access to your work, so I can understand that, but I can also see how someone holding onto an archive piece can feel a little hurt by the fact that this design is now available to the masses,” says Todisco. “Overall, though, usually when that happens, the OG pieces either tend to go up in value or and become more coveted. So, I think it's a positive.”

Dior Homme

Grid Breakdown:

  1. Dior Homme A/W 2003 Lurex-Blend Two-Button Blazer
  2. Dior Homme S/S 2002 Beaded Bloodwound Shirt
  3. Dior Homme A/W 2003 Waxed Clawmark Jeans
  4. Dior Homme A/W 2003 Neon Green Patent Belt
  5. Dior Homme A/W 2003 Leather and Waxed Knit Wool Gloves
  6. Dior Homme A/W 2007 Navigate Combat Boots

Todisco's Take: For a lot of sneakerheads, Dior denim was the entry point into high fashion. I know personally buying a pair of Dior denim in the Hedi Slimane era felt like: “Okay, cool, I made it. I have some taste now.” The fabric was Japanese, and the cut was far superior to what people were wearing during that time. It’s very full-circle that we’re able to bring it back in this outfitgrid.

Prada

Grid Breakdown:

  1. Prada A/W 1999 Leather Strap-Accented Suit
  2. Prada A/W 2016 “Impossible True Love” Shirt
  3. Prada S/S 1998 Gold Metallic Stitch-Accented Tank Top
  4. Prada A/W 2019 Trousers
  5. Prada Mid-2000s Leopard-Printed Ponyhair Baseball Cap
  6. Prada Mid-2000s America's Cup Sneakers

Todisco's Take: A lot of fashion sneakers are very derivative, but the Prada America's Cup sneaker has had such an iconic run over the years. At this point it's more nostalgia than a groundbreaking design. This is like wearing a pair of retro Nikes. The Supreme Air Max '98s literally took cues from it, so talk about full circle, right? The print on the button-down is insane. It's beautiful in person; it's a gorgeous piece and definitely a grail. It looks like it should be framed and put in a museum.

Helmut Lang

Grid Breakdown:

  1. Helmut Lang A/W 1999 Silver Astronaut Jacket
  2. Helmut Lang S/S 2005 Staff Logo Dress Shirt
  3. Helmut Lang S/S 1994 Spray-Painted Backstage Tank Top
  4. Helmut Lang S/S 1996 Classic Denim Jeans with Red Stripes
  5. Helmut Lang S/S 2003 Gun Holster Bag
  6. Helmut Lang Early-2000s Paint-Splattered German Army Trainers

Todisco's Take: The ‘99 Astronaut jacket was the standout piece from this collection and really shows off Helmut’s technical prowess. Drawing inspiration from NASA (something we still see decades later), Helmut created a futureproof piece with his precise placement of velcro straps, paneling, and fur. If you put this jacket on at midnight in 1999 you were undoubtedly shielded from any Y2K bugs.

Maison Margiela

Grid Breakdown:

  1. Maison Martin Margiela A/W 1999 Reversible Shearling Vest
  2. Maison Martin Margiela Spring/Summer 1998 Suede Flat Hook Jacket
  3. Maison Martin Margiela A/W 2002 Artisanal Reconstructed Levi's Denim
  4. Maison Martin Margiela Late-1990s Knit Long Tabi Gloves
  5. Maison Martin Margiela Spring/Summer 2002 Painted Square Toe Boots

Todisco's Take: These 2002 boots are incredible and wearable art. To me, they’re nail-on-the-head avant-garde Margiela. The crackling paint will only continue to look better the more you wear them, which further adds value to the archival value of older Margiela pieces. It’s also fascinating how Margiela challenged expectations of what “denim” could be with his reconstructed Levi’s. By removing pockets and leaving shadows of what once was, he was able to do something I don’t think many designers would dare to do in sacrificing function for creating a more streamlined minimal “pant.”

COMME des GARÇONS

Grid Breakdown:

  1. Junya Watanabe S/S 2007 Cargo Safari Shirt
  2. COMME des GARÇONS Mid-1990s Woven Relaxed Cargo Pants
  3. COMME des GARÇONS Homme Plus Mid-1980s Logo Graphic Turtleneck
  4. COMME des GARÇONS Mid-2010s Deconstructed Canvas Sneakers

Todisco's Take: This is a good overview at the different tiers of CDG and in traditional Outfitgrid manner, mixing old with new and multiple genres of the house. The deconstructed canvas sneakers in particular were my favorites - in how they flipped the Vans reference and brought in the cut-out holes, something that seems quite popular now and is a shape we commonly see referenced in CDG’s brand identity.

I think CDG’s definitely figured out the secret sauce to exist on multiple planes. For a lot of sneakerheads or core street wear consumers, their introduction to CDG may have come through Nike, Converse, or Supreme collaboration. And it’s interesting to see how that world has one interpretation of the brand, and then of course you have a different consumer that may be strictly geeking out on Junya or Homme Plus collections from years’ past. It draws parallels to Ralph Lauren, and how he’s able to speak to multiple consumers at the same time — both in terms of scale and coolness — which is really unique and powerful.

Jean Paul Gaultier

Grid Breakdown:

  1. Jean Paul Gaultier A/W 2007 Deconstructed Portrait Curved Knit
  2. Jean Paul Gaultier Late-1990s Remix Virus T-shirt
  3. Jean Paul Gaultier Mid-1990s Dragon-Printed Trousers
  4. Jean Paul Gaultier A/W 1993 Devil Horn Beanie
  5. Jean Paul Gaultier x Supreme S/S 2019 Vans Era Sneakers

Todisco's Take: JPG’s work has always felt more like art than clothing. It’s something I have appreciated from a distance as the unconventional cuts of his statement pieces are often beyond the scope of most consumer’s comfort level. This 2008 Curved knit is a perfect example of a beautifully intricate sweater with very detailed jacquard stitching and historical motifs, but something that’s relatively challenging to actually wear.

The late '90s Tour Shirt feels pretty timely given today’s climate, and Supreme’s even flipped it before. The Supreme x JPG x Vans (and entire collection) was an easy way to wear JPG. I think that’s the genius of Supreme in many of their “fashion” collaborations, in that they’re able to basically provide a translation service for the consumer, distilling something very intricate into something approachable, without sacrificing the DNA of the design.

Raf Simons

Grid Breakdown:

  1. Raf Simons x Sterling Ruby A/W 2014 Double-Breasted Tape Coat
  2. Raf Simons A/W 2016 Red Destroyed Varsity Sweater
  3. Raf Simons S/S 2000 Side-Zip Tailored Trousers
  4. Raf Simons x Sterling Ruby A/W 2014 Sample Bunny Boots

Todisco's Take: When the Sterling Ruby jacket came in, I threw it on immediately. I think it was 80 degrees, but I was like: “That’s a GOAT coat right there.” This is just the perfect marriage of art and fashion, a piece that would be insane to wear now, 20, 40 years from now — it’s timeless and collectible in that sense.

Raf Simons has really captured the essence of youth culture in his work and his recent appreciation by more mainstream music artists and icons has definitely shined more light on that. I love how he’s able to take something like a tattered varsity sweater, play with proportions and distressing, and make it a piece that you can throw on right away and know you’re getting a fit off.

What To Read Next