@pdxhb,
I love my Vans, too, which are the classic checkered slip-ons. Mine are 11 years old. They look better when they’re a little beat up looking, IMO. (My red Converses need more breaking-in. They’re too clean and neat.)
To give you an idea of what you can wear with Vans, it doesn’t have to be just jeans, shorts, and sweats. They look really good with casual dresses, like the ones from Gap or Zara. (These are my favorite stores to get easy, comfortable dresses.)
Mixing prints are fun as long as the colors complement each other. Peanuts print would spice things up!
Bag - Calista in tobacco Aquila matte
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