Start with the pieces you reach for most.
You do not need a perfect full-closet upload on day one. Adding the items you wear most often is enough to start getting more grounded recommendations.
As more wardrobe items are added, the recommendation engine gets a clearer picture of what is actually available to you.
Photograph items in good natural light when possible. Start with everyday layers, tops, bottoms, and shoes. Use the wardrobe view to confirm categories and clean up obvious mismatches.