1. Chuck Taylors
Why They’re Timeless: People have been wearing these shoes since the beginning of America, maybe. Also, they’re not that expensive and they go with absolutely everything.
Who Rocks Them: Kristen Stewart, like all the time, like even on the red carpet. Also: Rihanna, Zac Efron, Seth McFarlane, Lana del Rey, and the rest of the world.
Why They’re Timeless: Originally a skateboarding shoe, this is a California classic. They’re charm is that they’re simple looking and clean, so there’s no going wrong if you show up in these. Also they’re pretty pocket friendly.
Who Rocks Them: Pharrell, Rita Ora, Chris Brown, and Gwen Stefani.
5. Jack Purcells
Why They’re Timeless: These are probably the sleekest-looking sneakers on the list. You can dress them up or wear them down. So I would suggest just stocking up now in case they get discontinued or something. *Probably never going to happen, don’t worry.
Who Rocks Them: Ellen DeGeneres, Jennifer Garner, and Shiloh Jolie-Pitt.
6. New Balance 410 Retro Classic
Why They’re Timeless: Hands down, they are the best style of New Balance shoes in existence. All the other ones are kind of subpar. Meaning this is the shoe that has been keeping the company afloat since who only knows when, maybe.
Who Rocks Them: Ben Affleck, Heidi Klum, and Denzel Washington.
7. Timberland Boots
Why They’re Timeless: This is the only shoe on the list that hasn’t really changed its style or added lots of flashy colors and designs to its collection. The most popular style is still the simple beige boot we used to see in Biggie music videos in the ’90s.
Who Rocks Them: Khloe Kardashian, Amber Rose, Jay Z, and Kanye.
8. Adidas Superstar
Why They’re Timeless: There’s a song about them. Seriously what other shoe has a song made especially for it? (Please refer to the Run DMC song “My Adidas” if you’re drawing a blank right now)
Who Rocks Them: Jay Z, Will Smith, Russell Simmons, and probably the rest of the Simmons clan if you think about it.
9. Dr. Martens
Why They’re Timeless: Because you’ve never felt more badass than when you’re wearing these babies (see: Miley Cyrus’ “Wrecking Ball”). And because they come out with so many new style/colors/designs each year that there is really no need to branch out and buy something different.
Who Rocks Them: Miley Cyrus, Lorde, and Jessica Alba.
13. Retro Jordans
Why They’re Timeless: These will always be a favorite. You love them because they’re retro and because they’re hard to find/get sometimes. And when you do find them, can afford them, and don’t get hurt in the process it’s SO satisfying and totally worth it.
Who Rocks Them: Cara Delevigne, Kim Kardashian, and Beyoncé.
Why They’re Timeless: They’ve had the same design and colors in their selection since forever, yet you still you love these guys. They’re definitely the most sophisticated of the shoes on the list, and you could get away with wearing them to any occasion.
Who Rocks Them: Robert Pattinson, Ellen DeGeneres, and Florence Welch.
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