
Pimento Grilled Cheese Sandwiches are my go-to way to jazz up the familiar comfort of grilled cheese I started making these on lazy Saturdays for lunch and now my friends claim they are nothing short of crave-worthy The creamy pimento cheese filling melts perfectly between thick buttery bread creating a sandwich that is both rich and tangy with the perfect golden crunch
I first whipped these up for a picnic with friends and everyone was shocked by how addictive the tangy cheese filling was It has since become a must whenever I want cozy food with a little Southern flair
Ingredients
- Sharp cheddar cheese: brings rich nutty depth Use freshly shredded for best melt
- Diced pimento peppers: lend tangy sweetness Look for jars with good color and firm peppers
- Cream cheese: adds creamy texture Room temperature means easier mixing
- Mayonnaise: mixes it all together for rich smoothness Use real mayo
- Lemon juice: brightens up the flavors Fresh is best
- Fresh chives: add a mild oniony bite Snip right before using
- Kosher salt: for seasoning enhances every flavor
- Black pepper: adds a hint of heat Freshly cracked is ideal
- Unsalted butter: makes the bread crisp and rich Always use softened for easy spreading
- Italian seasonings: create herby notes You can use your favorite dried blend
- Texas toast or thick rustic bread: holds up well Choose a loaf with a crusty crumb so it does not get soggy
Step-by-Step Instructions
- Make the Pimento Cheese Filling:
- Mix the shredded cheddar diced pimentos cream cheese mayonnaise lemon juice chives salt and pepper in a medium bowl Stir thoroughly until everything is well blended and creamy Cover and chill for at least one hour This helps the flavors meld and thickens the mixture so it spreads easily
- Prepare the Bread:
- In a small bowl stir together softened butter Italian seasoning and salt Spread this herby butter mixture evenly onto one side of all eight bread slices This creates a crisp golden crust with extra flavor
- Assemble the Sandwiches:
- Lay out four slices of bread buttered side down on your work surface Spread about a third of a cup of the pimento cheese filling evenly onto each one Top with the remaining slices buttered side facing out so you have four sandwiches
- Cook the Sandwiches:
- Heat a large skillet over medium heat Once hot add the sandwiches Cook for three to four minutes on the first side until deep golden brown and crisp Gently flip each sandwich and cook another two to three minutes on the other side until everything is piping hot and the cheese is oozy and melted

My all-time favorite ingredient is the sharp cheddar It really gives the filling its punchy flavor I still remember my sister licking the mixing spoon clean the last time we made these together right in my tiny kitchen
Storage Tips
Store extra pimento cheese in an airtight container in the fridge for up to five days If you make extra sandwiches let them cool then wrap tightly and refrigerate They taste delicious cold or can be crisped up in a skillet the next day for a quick meal
Ingredient Substitutions
You can swap Monterey Jack or pepper jack for half the cheddar if you want a little more kick For gluten free sandwiches choose your favorite gluten free sandwich bread If you do not have Italian seasoning try a sprinkle of dried oregano and basil

Serving Suggestions
These sandwiches pair perfectly with tomato soup or a crisp dill pickle On hot days I like to serve them cut into fingers with lots of crunchy vegetables on the side They also make great snacks for movie night if you slice them into appetizers
Cultural and Historical Context
Pimento cheese is a Southern classic dating back to the early 1900s when home cooks combined cheddar and sweet pimento peppers as a spread It became a lunchtime favorite across the South and found its way into sandwiches at soda fountains and picnics alike
Recipe FAQs
- → How do you make the pimento cheese filling creamy?
Blend shredded sharp cheddar with cream cheese, mayo, and a touch of lemon juice until smooth. Letting it chill helps the flavors meld and yields a creamier texture.
- → What’s the best bread for grilled cheese sandwiches?
Thick-sliced rustic or Texas toast works best, offering a sturdy base that toasts beautifully while holding in the creamy filling.
- → Can I prepare the filling ahead of time?
Yes, the pimento cheese spread develops even better flavor after being refrigerated for at least an hour, or overnight if possible.
- → How can I make the sandwich extra crisp?
Butter the bread evenly and toast over medium-low heat, allowing each side to turn a deep golden brown without burning.
- → What sides pair well with pimento grilled cheese?
Serve alongside tomato soup, a crisp green salad, or crunchy pickles for a classic, well-rounded meal.