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On one end of the spectrum, we had outlandish styles like the fairy floss-coloured fur hat worn by Pamela Anderson to the 1999 VMAs, while on the other, we had the more wearable styles like the rolled brim hat modelled here by Claudia Schiffer
It has been 21 years since Hilton, now 42, first wore the look, but you'd never guess comparing the two images
An allover swirly, artsy, graphic, leafy, floral, dotted or leopard print works the same way in dresses
Black ankle boots and socks give it a grounded, urban edge, while the clean background and sunlight make the whole look feel fresh and high-fashion
Denim on Denim: A light-washed denim jacket paired with contrasting dark denim jeans, finished with canvas sneakers
These shoes give the vibes of simplicity and are casual to take on this ensemble indoors or outdoors
