Who Does The Grocery Shopping For The President? - Tasting Table
Briefly

The Presidential Food Service, staffed by Navy culinary specialists, provides all food for the White House and handles grocery procurement for the first family. The first family orders groceries from these specialists whenever they want items and receives a presidential bill for expenses. Orders are mainly placed with approved suppliers, but designated shoppers also visit farmer's markets and grocery stores to obtain specialty items. Shoppers vary times and locations to remain unnoticed and anticipate cravings to reduce unnecessary trips. All purchases are screened and prepared by White House chefs who cook to family tastes and follow requests.
As former First Lady Michelle Obama once explained on "Jimmy Kimmel Live," the first family orders groceries from the specialists whenever they want something, and they're later sent a presidential bill for the expense. The family can get virtually any item, no matter how hard it is to find. The orders are mainly placed with approved suppliers, but there are designated shoppers who go to farmer's markets and grocery stores too.
The shoppers tend to visit a number of different places at varying times so that they remain unnoticed, and they try to buy things they think the family might randomly crave in order to avoid unnecessary trips (via People). Of course, everything is screened and then prepared by the White House chefs, who cook to the family's tastes and follow any requests.
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