diff --git a/command/command.ts b/command/command.ts
index c2a80014..5261ad67 100644
--- a/command/command.ts
+++ b/command/command.ts
@@ -2148,16 +2148,20 @@ export class Command<
           };
 
           if (expectedArg.variadic) {
-            arg = args.splice(0, args.length).map((value) =>
-              parseArgValue(value)
-            );
+            arg = args
+              .splice(0, args.length)
+              .filter((arg) => !(expectedArg.optional && arg === ""))
+              .map((value) => parseArgValue(value));
           } else {
-            arg = parseArgValue(args.shift() as string);
+            const value = args.shift() as string;
+            if (!(expectedArg.optional && value === "")) {
+              arg = parseArgValue(value);
+            }
           }
 
           if (expectedArg.variadic && Array.isArray(arg)) {
             params.push(...arg);
-          } else if (typeof arg !== "undefined") {
+          } else {
             params.push(arg);
           }
         }
diff --git a/command/test/command/arguments_test.ts b/command/test/command/arguments_test.ts
index c3aa6563..897d04b5 100644
--- a/command/test/command/arguments_test.ts
+++ b/command/test/command/arguments_test.ts
@@ -94,6 +94,20 @@ test("should parse multi argument option", async () => {
   assertEquals(args, ["mod.ts"]);
 });
 
+test("should ignore optional arguments with an empty string as value", async () => {
+  const { args } = await new Command()
+    .arguments("[foo] [bar] [baz] [...beep]")
+    .parse(["", "bar-value", "", "", "", "beep-value-3", "", "beep-value-5"]);
+
+  assertEquals(args, [
+    undefined,
+    "bar-value",
+    undefined,
+    "beep-value-3",
+    "beep-value-5",
+  ]);
+});
+
 test("should throw an error for invalid number types", async () => {
   await assertRejects(
     async () => {
diff --git a/command/test/command/option_test.ts b/command/test/command/option_test.ts
index 76c99939..5cd9b644 100644
--- a/command/test/command/option_test.ts
+++ b/command/test/command/option_test.ts
@@ -275,3 +275,63 @@ test("command - option - global option value handler", async () => {
     .parse(["foo", "--foo", "bar"]);
   assertEquals(options, { foo: { value: "bar" } });
 });
+
+test("command - option - should skip optional arguments with an empty value", async () => {
+  const { options, args } = await new Command()
+    .noExit()
+    .option("--foo [value:number]", "...")
+    .option("--bar <value:boolean>", "...")
+    .option("--baz <value:string>", "...")
+    .option("--beep <value:string>", "...", { collect: true })
+    .option("--boop <value:number>", "...")
+    .option("--multi [value:string] [value:string] [value:string]", "...")
+    .option("--variadic [...value:string]", "...")
+    .parse([
+      "--foo",
+      "",
+      "--bar",
+      "",
+      "--baz",
+      "",
+      "--boop",
+      "1",
+      "--beep",
+      "",
+      "--beep",
+      "beep-value-2",
+      "--beep",
+      "",
+      "--beep",
+      "beep-value-4",
+      "--multi",
+      "",
+      "multi-value-2",
+      "",
+      "--variadic",
+      "",
+      "variadic-value-2",
+      "",
+      "variadic-value-4",
+      "",
+    ]);
+
+  assertEquals({ options, args }, {
+    options: {
+      beep: [
+        "beep-value-2",
+        "beep-value-4",
+      ],
+      boop: 1,
+      multi: [
+        undefined,
+        "multi-value-2",
+        undefined,
+      ],
+      variadic: [
+        "variadic-value-2",
+        "variadic-value-4",
+      ],
+    },
+    args: [],
+  });
+});
diff --git a/flags/flags.ts b/flags/flags.ts
index 23612dde..d38a89a4 100644
--- a/flags/flags.ts
+++ b/flags/flags.ts
@@ -148,6 +148,7 @@ function parseArgs<TFlagOptions extends FlagOptions>(
     let current: string = args[argsIndex];
     let currentValue: string | undefined;
     let negate = false;
+    let skipArgument = false;
 
     // literal args after --
     if (inLiteral) {
@@ -188,7 +189,7 @@ function parseArgs<TFlagOptions extends FlagOptions>(
     // split value: --foo="bar=baz" => --foo bar=baz
     const equalSignIndex = current.indexOf("=");
     if (equalSignIndex !== -1) {
-      currentValue = current.slice(equalSignIndex + 1) || undefined;
+      currentValue = current.slice(equalSignIndex + 1);
       current = current.slice(0, equalSignIndex);
     }
 
@@ -257,6 +258,10 @@ function parseArgs<TFlagOptions extends FlagOptions>(
 
     parseNext(option);
 
+    if (skipArgument) {
+      continue;
+    }
+
     if (typeof ctx.flags[propName] === "undefined") {
       if (option.args?.length && !option.args?.[optionArgsIndex].optional) {
         throw new MissingOptionValueError(option.name);
@@ -289,6 +294,8 @@ function parseArgs<TFlagOptions extends FlagOptions>(
     /** Parse next argument for current option. */
     // deno-lint-ignore no-inner-declarations
     function parseNext(option: FlagOptions): void {
+      let skipOptionArgument = false;
+
       if (negate) {
         setFlagValue(false);
         return;
@@ -360,6 +367,16 @@ function parseArgs<TFlagOptions extends FlagOptions>(
         }
       }
 
+      if (skipOptionArgument) {
+        if (hasNext(arg)) {
+          parseNext(option);
+        }
+        return;
+      }
+      if (skipArgument) {
+        return;
+      }
+
       if (
         typeof result !== "undefined" &&
         (option.args.length > 1 || arg.variadic)
@@ -367,6 +384,9 @@ function parseArgs<TFlagOptions extends FlagOptions>(
         if (!ctx.flags[propName]) {
           setFlagValue([]);
         }
+        if (result === "") {
+          result = undefined;
+        }
 
         (ctx.flags[propName] as Array<unknown>).push(result);
 
@@ -383,7 +403,7 @@ function parseArgs<TFlagOptions extends FlagOptions>(
           return false;
         }
         const nextValue = currentValue ?? args[argsIndex + 1];
-        if (!nextValue) {
+        if (nextValue === undefined) {
           return false;
         }
         if (option.args.length > 1 && optionArgsIndex >= option.args.length) {
@@ -414,17 +434,33 @@ function parseArgs<TFlagOptions extends FlagOptions>(
         arg: ArgumentOptions,
         value: string,
       ): unknown {
-        const result: unknown = opts.parse
-          ? opts.parse({
-            label: "Option",
-            type: arg.type || OptionType.STRING,
-            name: `--${option.name}`,
-            value,
-          })
-          : parseDefaultType(option, arg, value);
-
-        if (typeof result !== "undefined") {
+        let result: unknown;
+
+        if ((!option.required || arg.optional) && value === "") {
+          // if the value is empty and the argument is optional,
+          // we can skip the argument.
+          if (arg.variadic) {
+            skipOptionArgument = true;
+          } else if (option.args?.length === 1) {
+            skipArgument = true;
+          } else {
+            // will be mapped to undefined later.
+            result = "";
+          }
           increase = true;
+        } else {
+          result = opts.parse
+            ? opts.parse({
+              label: "Option",
+              type: arg.type || OptionType.STRING,
+              name: `--${option.name}`,
+              value,
+            })
+            : parseDefaultType(option, arg, value);
+
+          if (typeof result !== "undefined") {
+            increase = true;
+          }
         }
 
         return result;
diff --git a/flags/test/flags/empty_options_test.ts b/flags/test/flags/empty_options_test.ts
new file mode 100644
index 00000000..2f08fe08
--- /dev/null
+++ b/flags/test/flags/empty_options_test.ts
@@ -0,0 +1,92 @@
+import { test } from "@cliffy/internal/testing/test";
+import { assertEquals } from "@std/assert";
+import { parseFlags } from "../../flags.ts";
+
+test("[flags] should skip optional arguments with an empty value", () => {
+  const { flags, unknown, literal } = parseFlags(
+    [
+      "--foo",
+      "",
+      "--bar",
+      "",
+      "--baz",
+      "",
+      "--boop",
+      "1",
+      "--beep",
+      "",
+      "--beep",
+      "beep-value-2",
+      "--beep",
+      "",
+      "--beep",
+      "beep-value-4",
+      "--multi",
+      "",
+      "multi-value-2",
+      "",
+      "--variadic",
+      "",
+      "variadic-value-2",
+      "",
+      "variadic-value-4",
+      "",
+    ],
+    {
+      flags: [{
+        name: "foo",
+        type: "number",
+        optionalValue: true,
+      }, {
+        name: "bar",
+        type: "boolean",
+      }, {
+        name: "baz",
+        type: "string",
+      }, {
+        name: "beep",
+        type: "string",
+        collect: true,
+      }, {
+        name: "boop",
+        type: "number",
+      }, {
+        name: "multi",
+        args: [{
+          type: "string",
+          optional: true,
+        }, {
+          type: "string",
+          optional: true,
+        }, {
+          type: "string",
+          optional: true,
+        }],
+      }, {
+        name: "variadic",
+        type: "string",
+        optional: true,
+        variadic: true,
+      }],
+    },
+  );
+
+  assertEquals(flags, {
+    beep: [
+      "beep-value-2",
+      "beep-value-4",
+    ],
+    boop: 1,
+    multi: [
+      undefined,
+      "multi-value-2",
+      undefined,
+    ],
+    variadic: [
+      "variadic-value-2",
+      "variadic-value-4",
+    ],
+  });
+  assertEquals(unknown, []);
+  assertEquals(literal, []);
+});
diff --git a/flags/types/number.ts b/flags/types/number.ts
index f1d8ae7c..5efcb746 100644
--- a/flags/types/number.ts
+++ b/flags/types/number.ts
@@ -3,9 +3,11 @@ import { InvalidTypeError } from "../_errors.ts";
 
 /** Number type handler. Excepts any numeric value. */
 export const number: TypeHandler<number> = (type: ArgumentValue): number => {
-  const value = Number(type.value);
-  if (Number.isFinite(value)) {
-    return value;
+  if (type.value) {
+    const value = Number(type.value);
+    if (Number.isFinite(value)) {
+      return value;
+    }
   }
 
   throw new InvalidTypeError(type);