diff --git a/core/src/main/scala/chisel3/Data.scala b/core/src/main/scala/chisel3/Data.scala
index b83fb53e61f..7975cbdfe6a 100644
--- a/core/src/main/scala/chisel3/Data.scala
+++ b/core/src/main/scala/chisel3/Data.scala
@@ -5,7 +5,7 @@ package chisel3
 import chisel3.experimental.dataview.reify
 
 import scala.language.experimental.macros
-import chisel3.experimental.{Analog, BaseModule, DataMirror, FixedPoint, Interval}
+import chisel3.experimental.{Analog, BaseModule, DataMirror, EnumType, FixedPoint, Interval}
 import chisel3.internal.Builder.pushCommand
 import chisel3.internal._
 import chisel3.internal.firrtl._
@@ -895,6 +895,84 @@ abstract class Data extends HasId with NamedComponent with SourceInfoDoc {
   def toPrintable: Printable
 }
 
+object Data {
+
+  /**
+    * Provides generic, recursive equality for [[Bundle]] and [[Vec]] hardware. This avoids the
+    * need to use workarounds such as `bundle1.asUInt === bundle2.asUInt` by allowing users
+    * to instead write `bundle1 === bundle2`.
+    *
+    * Static type safety of this comparison is guaranteed at compile time as the extension
+    * method requires the same parameterized type for both the left-hand and right-hand
+    * sides. It is, however, possible to get around this type safety using `Bundle` subtypes
+    * that can differ during runtime (e.g. through a generator). These cases are
+    * subsequently raised as elaboration errors.
+    *
+    * @param lhs The [[Data]] hardware on the left-hand side of the equality
+    */
+  implicit class DataEquality[T <: Data](lhs: T)(implicit sourceInfo: SourceInfo, compileOptions: CompileOptions) {
+
+    /** Dynamic recursive equality operator for generic [[Data]]
+      *
+      * @param rhs a hardware [[Data]] to compare `lhs` to
+      * @return a hardware [[Bool]] asserted if `lhs` is equal to `rhs`
+      * @throws ChiselException when `lhs` and `rhs` are different types during elaboration time
+      */
+    def ===(rhs: T): Bool = {
+      (lhs, rhs) match {
+        case (thiz: UInt, that: UInt) => thiz === that
+        case (thiz: SInt, that: SInt) => thiz === that
+        case (thiz: AsyncReset, that: AsyncReset) => thiz.asBool === that.asBool
+        case (thiz: Reset, that: Reset) => thiz === that
+        case (thiz: Interval, that: Interval) => thiz === that
+        case (thiz: FixedPoint, that: FixedPoint) => thiz === that
+        case (thiz: EnumType, that: EnumType) => thiz === that
+        case (thiz: Clock, that: Clock) => thiz.asUInt === that.asUInt
+        case (thiz: Vec[_], that: Vec[_]) =>
+          if (thiz.length != that.length) {
+            throwException(s"Cannot compare Vecs $thiz and $that: Vec sizes differ")
+          } else {
+            thiz.getElements
+              .zip(that.getElements)
+              .map { case (thisData, thatData) => thisData === thatData }
+              .reduce(_ && _)
+          }
+        case (thiz: Record, that: Record) =>
+          if (thiz.elements.size != that.elements.size) {
+            throwException(s"Cannot compare Bundles $thiz and $that: Bundle types differ")
+          } else {
+            thiz.elements.map {
+              case (thisName, thisData) =>
+                if (!that.elements.contains(thisName))
+                  throwException(
+                    s"Cannot compare Bundles $thiz and $that: field $thisName (from $thiz) was not found in $that"
+                  )
+
+                val thatData = that.elements(thisName)
+
+                try {
+                  thisData === thatData
+                } catch {
+                  case e: ChiselException =>
+                    throwException(
+                      s"Cannot compare field $thisName in Bundles $thiz and $that: ${e.getMessage.split(": ").last}"
+                    )
+                }
+            }
+              .reduce(_ && _)
+          }
+        // This should be matching to (DontCare, DontCare) but the compiler wasn't happy with that
+        case (_: DontCare.type, _: DontCare.type) => true.B
+
+        case (thiz: Analog, that: Analog) =>
+          throwException(s"Cannot compare Analog values $thiz and $that: Equality isn't defined for Analog values")
+        // Runtime types are different
+        case (thiz, that) => throwException(s"Cannot compare $thiz and $that: Runtime types differ")
+      }
+    }
+  }
+}
+
 trait WireFactory {
 
   /** Construct a [[Wire]] from a type template
diff --git a/src/test/scala/chiselTests/DataEqualitySpec.scala b/src/test/scala/chiselTests/DataEqualitySpec.scala
new file mode 100644
index 00000000000..4ac3292dcf4
--- /dev/null
+++ b/src/test/scala/chiselTests/DataEqualitySpec.scala
@@ -0,0 +1,257 @@
+package chiselTests
+
+import chisel3._
+import chisel3.experimental.VecLiterals._
+import chisel3.experimental.BundleLiterals._
+import chisel3.experimental.{Analog, ChiselEnum, ChiselRange, FixedPoint, Interval}
+import chisel3.stage.ChiselStage
+import chisel3.testers.BasicTester
+import chisel3.util.Valid
+
+class EqualityModule(lhsGen: => Data, rhsGen: => Data) extends Module {
+  val out = IO(Output(Bool()))
+
+  val lhs = lhsGen
+  val rhs = rhsGen
+
+  out := lhs === rhs
+}
+
+class EqualityTester(lhsGen: => Data, rhsGen: => Data) extends BasicTester {
+  val module = Module(new EqualityModule(lhsGen, rhsGen))
+
+  assert(module.out)
+
+  stop()
+}
+
+class AnalogBundle extends Bundle {
+  val analog = Analog(32.W)
+}
+
+class AnalogExceptionModule extends Module {
+  class AnalogExceptionModuleIO extends Bundle {
+    val bundle1 = new AnalogBundle
+    val bundle2 = new AnalogBundle
+  }
+
+  val io = IO(new AnalogExceptionModuleIO)
+}
+
+class AnalogExceptionTester extends BasicTester {
+  val module = Module(new AnalogExceptionModule)
+
+  module.io.bundle1 <> DontCare
+  module.io.bundle2 <> DontCare
+
+  assert(module.io.bundle1 === module.io.bundle2)
+
+  stop()
+}
+
+class DataEqualitySpec extends ChiselFlatSpec with Utils {
+  object MyEnum extends ChiselEnum {
+    val sA, sB = Value
+  }
+  object MyEnumB extends ChiselEnum {
+    val sA, sB = Value
+  }
+  class MyBundle extends Bundle {
+    val a = UInt(8.W)
+    val b = Bool()
+    val c = MyEnum()
+  }
+  class LongBundle extends Bundle {
+    val a = UInt(48.W)
+    val b = SInt(32.W)
+    val c = FixedPoint(16.W, 4.BP)
+  }
+  class RuntimeSensitiveBundle(gen: => Bundle) extends Bundle {
+    val a = UInt(8.W)
+    val b: Bundle = gen
+  }
+
+  behavior.of("UInt === UInt")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(0.U, 0.U)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(0.U, 1.U)
+    }
+  }
+
+  behavior.of("SInt === SInt")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(0.S, 0.S)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(0.S, 1.S)
+    }
+  }
+
+  behavior.of("Reset === Reset")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(true.B, true.B)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(true.B, false.B)
+    }
+  }
+
+  behavior.of("AsyncReset === AsyncReset")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(true.B.asAsyncReset, true.B.asAsyncReset)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(true.B.asAsyncReset, false.B.asAsyncReset)
+    }
+  }
+
+  behavior.of("Interval === Interval")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(2.I, 2.I)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(2.I, 3.I)
+    }
+  }
+
+  behavior.of("FixedPoint === FixedPoint")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(4.5.F(16.W, 4.BP), 4.5.F(16.W, 4.BP))
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(4.5.F(16.W, 4.BP), 4.6.F(16.W, 4.BP))
+    }
+  }
+
+  behavior.of("ChiselEnum === ChiselEnum")
+  it should "pass with equal values" in {
+    assertTesterPasses {
+      new EqualityTester(MyEnum.sA, MyEnum.sA)
+    }
+  }
+  it should "fail with differing values" in {
+    assertTesterFails {
+      new EqualityTester(MyEnum.sA, MyEnum.sB)
+    }
+  }
+
+  behavior.of("Vec === Vec")
+  it should "pass with equal sizes, equal values" in {
+    assertTesterPasses {
+      new EqualityTester(
+        Vec(3, UInt(8.W)).Lit(0 -> 1.U, 1 -> 2.U, 2 -> 3.U),
+        Vec(3, UInt(8.W)).Lit(0 -> 1.U, 1 -> 2.U, 2 -> 3.U)
+      )
+    }
+  }
+  it should "fail with equal sizes, differing values" in {
+    assertTesterFails {
+      new EqualityTester(
+        Vec(3, UInt(8.W)).Lit(0 -> 1.U, 1 -> 2.U, 2 -> 3.U),
+        Vec(3, UInt(8.W)).Lit(0 -> 0.U, 1 -> 1.U, 2 -> 2.U)
+      )
+    }
+  }
+  it should "throw a ChiselException with differing sizes" in {
+    (the[ChiselException] thrownBy extractCause[ChiselException] {
+      assertTesterFails {
+        new EqualityTester(
+          Vec(3, UInt(8.W)).Lit(0 -> 1.U, 1 -> 2.U, 2 -> 3.U),
+          Vec(4, UInt(8.W)).Lit(0 -> 1.U, 1 -> 2.U, 2 -> 3.U, 3 -> 4.U)
+        )
+      }
+    }).getMessage should include("Vec sizes differ")
+  }
+
+  behavior.of("Bundle === Bundle")
+  it should "pass with equal type, equal values" in {
+    assertTesterPasses {
+      new EqualityTester(
+        (new MyBundle).Lit(_.a -> 42.U, _.b -> false.B, _.c -> MyEnum.sB),
+        (new MyBundle).Lit(_.a -> 42.U, _.b -> false.B, _.c -> MyEnum.sB)
+      )
+    }
+  }
+  it should "fail with equal type, differing values" in {
+    assertTesterFails {
+      new EqualityTester(
+        (new MyBundle).Lit(_.a -> 42.U, _.b -> false.B, _.c -> MyEnum.sB),
+        (new MyBundle).Lit(_.a -> 42.U, _.b -> false.B, _.c -> MyEnum.sA)
+      )
+    }
+  }
+  it should "throw a ChiselException with differing runtime types" in {
+    (the[ChiselException] thrownBy extractCause[ChiselException] {
+      assertTesterFails {
+        new EqualityTester(
+          (new RuntimeSensitiveBundle(new MyBundle)).Lit(
+            _.a -> 1.U,
+            _.b -> (new MyBundle).Lit(
+              _.a -> 42.U,
+              _.b -> false.B,
+              _.c -> MyEnum.sB
+            )
+          ),
+          (new RuntimeSensitiveBundle(new LongBundle)).Lit(
+            _.a -> 1.U,
+            _.b -> (new LongBundle).Lit(
+              _.a -> 42.U,
+              _.b -> 0.S,
+              _.c -> 4.5.F(16.W, 4.BP)
+            )
+          )
+        )
+      }
+    }).getMessage should include("Runtime types differ")
+  }
+
+  behavior.of("DontCare === DontCare")
+  it should "pass with two invalids" in {
+    assertTesterPasses {
+      new EqualityTester(Valid(UInt(8.W)).Lit(_.bits -> 123.U), Valid(UInt(8.W)).Lit(_.bits -> 123.U))
+    }
+  }
+  it should "exhibit the same behavior as comparing two invalidated wires" in {
+    // Also check that two invalidated wires are equal
+    assertTesterPasses {
+      new EqualityTester(WireInit(UInt(8.W), DontCare), WireInit(UInt(8.W), DontCare))
+    }
+
+    // Compare the verilog generated from both test cases and verify that they both are equal to true
+    val verilog1 = ChiselStage.emitVerilog(
+      new EqualityModule(Valid(UInt(8.W)).Lit(_.bits -> 123.U), Valid(UInt(8.W)).Lit(_.bits -> 123.U))
+    )
+    val verilog2 =
+      ChiselStage.emitVerilog(new EqualityModule(WireInit(UInt(8.W), DontCare), WireInit(UInt(8.W), DontCare)))
+
+    verilog1 should include("assign out = 1'h1;")
+    verilog2 should include("assign out = 1'h1;")
+  }
+
+  behavior.of("Analog === Analog")
+  it should "throw a ChiselException" in {
+    (the[ChiselException] thrownBy extractCause[ChiselException] {
+      assertTesterFails { new AnalogExceptionTester }
+    }).getMessage should include("Equality isn't defined for Analog values")
+  }
+}