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As Into the Gloss points out, it's been almost 20 years to the day since Alicia Silverstone broke out with the Aerosmith video "Cryin." It took that long for the look that Silverstone and fellow video babe Liv Tyler made iconic (flippy floral dresses, plaid miniskirts, baby tees, lace-up combat boots) to cycle back to popularity.
This image—of model Helena Vestergaard (with her much-older rock star boyfriend Anthony Kiedis) at NYFW—reminded us of the many style possibilities of chunky black boots. After the jump, find seven pairs that are more Kate Moss circa the Johnny Depp years and less Courtney Love circa any era.
- Zara track sole ankle boot with laces, $99.90.
- Chippewa black oiled insulated ladies logger, $168.95.
- Cheap Monday chunky heel lace-up booties, $180.
- John Lewis Bertie Pane heeled lace-up boot, $185.89.
- Rag & Bone cozen boot, $595.
- Prada buckled strap lace-up ankle boot, $790.
- Saint Laurent studded rangers boot, $1,995.