Preheat oven to 350°F and line 2 muffin pans with 15 cupcake liners.
In a large bowl, whisk all the dry ingredients together.
1 & 1/2 cup all-purpose flour, 1 cup sugar, 1 tsp baking soda, 1/2 tsp salt
Add the 1 cup of milk, oil, and vanilla to the flour mixture. Stir until just combined.
1 cup whole milk, 1/2 cup vegetable oil, 1 Tbsp vanilla
Add vinegar, stir and scrap around the sides and bottom of bowl to incorporate all the flour. Whisk until just blended.
1 Tbsp white vinegar
Spoon 1 full tbsp of the vanilla batter into each cupcake liner. Then add the cocoa powder and 1 tbsp of milk to the remaining batter and mix until just blended. Divide the rest of the chocolate batter into the 15 cupcake liners.
Using a butter knife, gently swirl the batter from the bottom up to bring some of the vanilla batter to the top.
Bake for about 15-18 minutes or just until a toothpick inserted in the center comes out clean. Let cupcakes completely cool before frosting.
To make buttercream:
Using an electric mixer, beat the butter and jam together until combined.
1 cup unsalted butter, 1/2 cup seedless strawberry jam
Add 1 cup of icing sugar at a time, mixing well after each addition.
3 cups icing sugar
Frost cupcakes as desired. I used a Wilton 1M tip, piping in a circular motion from the center of the cupcake outwards and back to the center. I also added some sprinkles for fun.
Notes
Cupcakes will keep for up to 4 days stored in an airtight container in the refrigerator