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Making a list like this is making a distinction between sneakers and boots. Growing up there wasn’t always a clear line between choices. Boots were as common as wearing J’s. Me personally, I would say in the beginning wearing boots was just a smart financial choice. My parents were not in any position to pour their hard earned into an infinite rotation of the latest and greatest. Boots were something I could wear for a long period of time without looking uncool — especially through the hell we called winter. On the flip side of that coin, boots represented something else to me. They were a symbol of handling your business, standing on your own, not swaying and following the trends. I still stand by those attributes today and still wear boots regardless of how much eBay heat is in storage. —FRANK THE BUTCHER
RELATED: The 10 Best Duck Boots for Winter
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25. Nike ACG Goadome
Frank says: "Some people wear these ACGs regardless of the season, temperature and weather. Had to make the list on the strength of the loyalty people have for this model. From Harlem to DC — streets were on fire."
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24. Timberland Black Chukka
Frank says: "'Throw Your Guns in the Air!!!!' —Onyx"
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23. Red Wing 875 (Concepts)
Frank says: "The response was so overwhelming with people calling Concepts a year after the drop. It was a sleeper classic and was a major milestone for Concepts projects."
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22. Visvim 7 Hole '73 Folk Boot
Frank says: "Jesus Christ, Visvim is so on point. Amazing."
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21. LL Bean Signature Boot
Frank says: "Where it all began. Pay homage."
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20. Asolo Fugitive GTX
Frank says: "Not my favorite Asolo, but its hard to locate what was valuable to me so long ago. This plays a close second and is for sure one of my favorite boots of all time."
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19. Eastland Classic Boot
Frank says: "This was that Spanish pretty boy boot back in the day. This was high end in high school, haha."
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18. Danner Mountain Light
Frank says: "So classic. Family owned & run and made in Portland. The Mountain Light is a boot everyone I spoke to agree should be on a top boot list. BTC x Danner coming soon."
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17. Dolomite Tibet Gore-Tex Boot
Frank says: "This boot was so in demand!! Started popping up around my way when people would visit their families or friends in NYC. Harder to get in Massachusetts in the beginning but these were the definitive 90’s Gore-Tex steez."
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16. Polo Ranger Boot (Cookie Boot)
Frank says: "Polo is a religion. I might not be an orthodox practicing Polo Rican at the moment, but I still believe. Just fly as hell. Shout to my guy Big Vic Lo."
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15. Nike ACG Son Of Lava Dome Hi
Frank says: "Just an example of Nike ACG's dominance in the 90s."
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14. Sorel Caribou
Frank says: "I live 50 minutes west of Boston in a spot where it always gets the worst weather. If metro Boston gets three inches of snow, I’ll get six inches. Lucky me. I wear my Caribou when Armageddon hits. Greg Lucci of Gourmet told me stories of the Caribou being the first unofficial snowboard boot. He would literally strap them into his binding."
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13. Nike ACG Baltoro
Frank says: "Soooo dope. ACG was created for real-deal hikers, but the colors pulled the rest of us in. I would hike to the corner store in these."
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12. Timberland Euro Hiker "Brown"
Frank says: "As a kid this was a neighborhood favorite, but once the girls in school got on them, I moved on. Still a classic. Shouts to Supreme for bringing light to them with their recent project."
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11. Visvim Grizzly Boot
Frank says: "This is the one of the only new boots on my list and it deserves to be here. I’m not sure what drugs Hiroki of Visvim is on, but I need a bundle. Design, innovation, execution and close attention to every painstaking detail makes Visvim product legendary. You will have this boot forever — and for the price you better."
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10. Vasque Skywalk "Tan/Navy"
Frank says: "My close friend Jon Piniero from the Bronx put me on to these in the mid '90s and I was instantly in love. Nothing beats the Tan (almost Bone) / Navy combo. Vasque in the past years went urban with the brand, but I pray they return to their roots."
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9. Timberland Iditarod Superboot (40 Belows)
Frank says: "East Coast early to mid '90s must-have. The 40 Below was the boot of all boots with a stature as tall as the boot itself. Not for the faint of heart, this model was statement. I applaud Alife for bringing this boot back in the fall of 2009. Bishop had a gun tucked in his. 'Yo, Q!'"
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8. Timberland 6” Field Boot x Concepts – ConOps
Frank says: "How dare I put something I worked on on this list? I know man.
"I respect the legacy of Timberland too much to pretend that I can slide one onto the list above them, but this situation is different. I had the opportunity to take on the 6” Timberland Field Boot as a project for Concepts and made the boot almost indestructible. All blacked-out military grade materials and a puncture-proof sole made the‘Con-Ops’ boot something I will own forever. We took something great and made it bombproof. Shouts to all the heads that continue to tell me that it’s their favorite boot."
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7. Red Wing 875
Frank says: "I knew this boot existed, but it wasn’t something I would wear until I worked on one with Red Wing via Concepts. Red Wing found perfection with this model."
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6. Merrell Wilderness
Frank says: "This boot is no joke. Great shape and classic look. Doesn't get much better."
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5. Timberland Field Boot "Mac & Cheese"
Frank says: "The classic alternative to the 'Beef & Broc' is the 'Mac & Cheese.' Not sure who came up with the foodie titles but they stuck. Another staple."
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4. Timberland 6” Premium "Black Nubuck"
Frank says: "This is the only other 6” Premium version that will get my respect. So don’t show up with a royal blue pair or get clowned out your shoes. This boot also sits comfortably with a high-end getup — word to @BrekOne."
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3. Timberland Field Boot "Beef & Broccoli"
Frank says: "The infamous ‘Beef & Broc’ is a hood staple with the most-copied colorway next to the neon Air Max 95 and Bulls/Jordan color palette."
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2. Vasque Sundowner "Maroon"
Frank says: "A gem. The Sundowner is an amazing boot. Previously made in Italy and was my first Gore-Tex purchase. I love the black version but the maroon is just synonymous with this model. OGs know about this one."
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1. Timberland 6” Premium "Wheat"
Frank says: "The king of boots is the 6” Premium Wheat. There is nothing more perfect in all of footwear to me, sneakers included. The shape, nubuck, ankle padding and lug sole are all trademarks made famous by Timberland model 10061. This boot has been my go-to since the age of 13, and every year since I have had multiple pairs on deck ready for action. I don’t care who used to wear them, who currently wears them or who’s the next to announce that they are 'off that.' I’m staying put."