Madison Bailey on her fashion week must-haves and failsafe getting ready playlist

Exploring nautical motifs, Tommy Hilfiger's latest Spring/Summer 2025 show seamlessly combined the brand's maritime inspirations, which have defined it since 1885. Hosted on the decommissioned MV John F. Kennedy, attendees spanned across different media and industries. There was no shortage of brilliance amongst the FROW. From Damson Idris to Tenashe, guests were presented with the brand's latest offerings, which included classic Breton stripes and regatta jackets.

We had the pleasure of catching up with one specific avid attendee, actress and model Madison Bailey, who talked us through her pre-show prep. Talking us through her classic Oxford dress and knee-high boots combo, fashion week handbag essentials, and her go-to getting-ready playlist, read below to find out how an A-lister prepares for New York Fashion Week...

The Outfit

Can you talk us through your outfit for Tommy Hilfiger’s fashion show?
We went with a classic Oxford layered under a cord mini! Chic and fun for fall with extra points for comfort.

The Essentials

My essentials include: eye patches, a charging block, a speaker for glam, my Canon camera for content, and bandaids for blisters!

The Playlist

What do you listen to when you’re getting ready?
I listen to Rihanna, Chappell Roan, Beyoncé- all of the girlies!

Favourite Fashion Trends

Which trends are you buying into for this and next season?
I have always and will always stan cheetah print, regardless of whether it's trending or not! I’m also taking my cowboy boots into next season, no matter what!

Instagrammable Spots

What is the most Instagrammable spot in NYC?
You tell me!! I’m never here enough.