Who was Shailene Woodley seen with at Milan Fashion Week?

Shailene Woodley was seen with Milo Callaghan at Milan Fashion Week.

When did Shailene Woodley and Lucas Bravo break up?

Shailene Woodley's breakup with Lucas Bravo was confirmed in September 2025.

What did Shailene Woodley wear during her Milan outing?

Shailene Woodley wore a sleek, all-black ensemble with flair pants and a blazer during her outing in Milan.

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Shailene Woodley Spotted With New Man After Bravo Breakup

26 Feb

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Summary

Shailene Woodley and Milo Callaghan seen together in Milan.
Their outing occurred during Milan Fashion Week in February 2026.
This follows Woodley's September 2025 breakup with Lucas Bravo.

Shailene Woodley Spotted With New Man After Bravo Breakup

Shailene Woodley and Milo Callaghan made a public appearance together during Milan Fashion Week in Italy on February 25, 2026. The pair were seen walking through the city streets, signaling a potential new romance.

Woodley, 34, was dressed in a chic all-black ensemble, complemented by a gold handbag. Callaghan, 28, opted for a more casual look with jeans and a leather jacket. This sighting occurred approximately five months after the confirmation of Woodley's separation from actor Lucas Bravo in September 2025, ending their whirlwind relationship.

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