diff --git a/__fixtures__/arbitraryValues/arbitraryValues.js b/__fixtures__/arbitraryValues/arbitraryValues.js
index 00a68910..b883d10f 100644
--- a/__fixtures__/arbitraryValues/arbitraryValues.js
+++ b/__fixtures__/arbitraryValues/arbitraryValues.js
@@ -8,6 +8,8 @@ tw`bg-opacity-[0.11]`
 tw`bg-opacity-[var(--value)]`
 tw`border-[#f00]`
 tw`border-[2.5px]`
+tw`border-t-[#f00]`
+tw`border-t-[2.5px]`
 tw`w-[3.23rem]`
 tw`w-[calc(100%+1rem)]`
 tw`w-[calc(var(--10-10px,calc(-20px-(-30px--40px)))-50px)]`
diff --git a/__fixtures__/directionalBorders/directionalBorders.js b/__fixtures__/directionalBorders/directionalBorders.js
new file mode 100644
index 00000000..38c17cae
--- /dev/null
+++ b/__fixtures__/directionalBorders/directionalBorders.js
@@ -0,0 +1,29 @@
+import tw from './macro' // twinImport
+
+tw`border-t`
+tw`border-r`
+tw`border-b`
+tw`border-l`
+
+tw`border-t-transparent`
+tw`border-t-current`
+tw`border-t-gray-50`
+
+tw`border-r-transparent`
+tw`border-r-current`
+tw`border-r-gray-50`
+
+tw`border-b-transparent`
+tw`border-b-current`
+tw`border-b-gray-50`
+
+tw`border-l-transparent`
+tw`border-l-current`
+tw`border-l-gray-50`
+
+tw`border-l-gray-50/20`
+
+tw`border-t-4`
+tw`border-r-4`
+tw`border-b-4`
+tw`border-l-4`
diff --git a/__snapshots__/plugin.test.js.snap b/__snapshots__/plugin.test.js.snap
index e7e5dec3..e6b47e97 100644
--- a/__snapshots__/plugin.test.js.snap
+++ b/__snapshots__/plugin.test.js.snap
@@ -2245,6 +2245,8 @@ tw\`bg-opacity-[0.11]\`
 tw\`bg-opacity-[var(--value)]\`
 tw\`border-[#f00]\`
 tw\`border-[2.5px]\`
+tw\`border-t-[#f00]\`
+tw\`border-t-[2.5px]\`
 tw\`w-[3.23rem]\`
 tw\`w-[calc(100%+1rem)]\`
 tw\`w-[calc(var(--10-10px,calc(-20px-(-30px--40px)))-50px)]\`
@@ -2379,6 +2381,13 @@ tw\`md:text-[red]\`
 ;({
   borderWidth: '2.5px',
 })
+;({
+  '--tw-border-opacity': '1',
+  borderTopColor: 'rgba(255, 0, 0, var(--tw-border-opacity))',
+})
+;({
+  borderTopWidth: '2.5px',
+})
 ;({
   width: '3.23rem',
 })
@@ -8452,6 +8461,112 @@ tw\`bg-blue-gray-green-pink\`
 })
 
 
+`;
+
+exports[`twin.macro directionalBorders.js: directionalBorders.js 1`] = `
+
+import tw from './macro' // twinImport
+
+tw\`border-t\`
+tw\`border-r\`
+tw\`border-b\`
+tw\`border-l\`
+
+tw\`border-t-transparent\`
+tw\`border-t-current\`
+tw\`border-t-gray-50\`
+
+tw\`border-r-transparent\`
+tw\`border-r-current\`
+tw\`border-r-gray-50\`
+
+tw\`border-b-transparent\`
+tw\`border-b-current\`
+tw\`border-b-gray-50\`
+
+tw\`border-l-transparent\`
+tw\`border-l-current\`
+tw\`border-l-gray-50\`
+
+tw\`border-l-gray-50/20\`
+
+tw\`border-t-4\`
+tw\`border-r-4\`
+tw\`border-b-4\`
+tw\`border-l-4\`
+
+      ↓ ↓ ↓ ↓ ↓ ↓
+
+// twinImport
+;({
+  borderTopWidth: '1px',
+})
+;({
+  borderRightWidth: '1px',
+})
+;({
+  borderBottomWidth: '1px',
+})
+;({
+  borderLeftWidth: '1px',
+})
+;({
+  borderTopColor: 'rgba(0, 0, 0, 0)',
+})
+;({
+  borderTopColor: 'currentColor',
+})
+;({
+  '--tw-border-opacity': '1',
+  borderTopColor: 'rgba(249, 250, 251, var(--tw-border-opacity))',
+})
+;({
+  borderRightColor: 'rgba(0, 0, 0, 0)',
+})
+;({
+  borderRightColor: 'currentColor',
+})
+;({
+  '--tw-border-opacity': '1',
+  borderRightColor: 'rgba(249, 250, 251, var(--tw-border-opacity))',
+})
+;({
+  borderBottomColor: 'rgba(0, 0, 0, 0)',
+})
+;({
+  borderBottomColor: 'currentColor',
+})
+;({
+  '--tw-border-opacity': '1',
+  borderBottomColor: 'rgba(249, 250, 251, var(--tw-border-opacity))',
+})
+;({
+  borderLeftColor: 'rgba(0, 0, 0, 0)',
+})
+;({
+  borderLeftColor: 'currentColor',
+})
+;({
+  '--tw-border-opacity': '1',
+  borderLeftColor: 'rgba(249, 250, 251, var(--tw-border-opacity))',
+})
+;({
+  borderLeftColor: 'rgba(249, 250, 251, 0.2)',
+})
+;({
+  borderTopWidth: '4px',
+})
+;({
+  borderRightWidth: '4px',
+})
+;({
+  borderBottomWidth: '4px',
+})
+;({
+  borderLeftWidth: '4px',
+})
+
+
 `;
 
 exports[`twin.macro disableColorVariables.js: disableColorVariables.js 1`] = `
diff --git a/src/config/dynamicStyles.js b/src/config/dynamicStyles.js
index 21c9d41b..207f2f79 100644
--- a/src/config/dynamicStyles.js
+++ b/src/config/dynamicStyles.js
@@ -341,49 +341,43 @@ export default {
 
   // https://tailwindcss.com/docs/border-width
   'border-t': {
-    prop: 'borderTopWidth',
     value: ['color', 'length'],
-    config: 'borderWidth',
+    plugin: 'border',
     coerced: {
       color: { property: 'borderTopColor', variable: '--tw-border-opacity' },
       length: { property: 'borderTopWidth' },
     },
   },
   'border-b': {
-    prop: 'borderBottomWidth',
     value: ['color', 'length'],
-    config: 'borderWidth',
+    plugin: 'border',
     coerced: {
       color: { property: 'borderBottomColor', variable: '--tw-border-opacity' },
       length: { property: 'borderBottomWidth' },
     },
   },
   'border-l': {
-    prop: 'borderLeftWidth',
     value: ['color', 'length'],
-    config: 'borderWidth',
+    plugin: 'border',
     coerced: {
       color: { property: 'borderLeftColor', variable: '--tw-border-opacity' },
       length: { property: 'borderLeftWidth' },
     },
   },
   'border-r': {
-    prop: 'borderRightWidth',
     value: ['color', 'length'],
-    config: 'borderWidth',
+    plugin: 'border',
     coerced: {
       color: { property: 'borderRightColor', variable: '--tw-border-opacity' },
       length: { property: 'borderRightWidth' },
     },
   },
-
   'border-opacity': {
     prop: '--tw-border-opacity',
     config: 'borderOpacity',
     configFallback: 'opacity',
   },
   border: {
-    prop: 'borderWidth',
     value: ['color', 'length'],
     plugin: 'border',
     coerced: {
diff --git a/src/handlers/corePlugins.js b/src/handlers/corePlugins.js
index a4fdda23..4299499c 100644
--- a/src/handlers/corePlugins.js
+++ b/src/handlers/corePlugins.js
@@ -58,7 +58,7 @@ const getMatchConfigValue = ({ match, theme, getConfigValue }) => (
   regexMatch
 ) => {
   const matcher = match(regexMatch)
-  if (!matcher) return
+  if (matcher === undefined) return
   return getConfigValue(theme(config), matcher)
 }
 
@@ -73,7 +73,11 @@ export default ({
   ...rest
 }) => {
   const errors = getErrors({ state, pieces, dynamicKey })
-  const match = regex => get(pieces.className.match(regex), [0]) || null
+  const match = regex => {
+    const result = get(pieces.className.match(regex), [0])
+    if (result === undefined) return
+    return result
+  }
 
   const matchConfigValue = getMatchConfigValue({ match, theme, getConfigValue })
   const toColor = getColor({
diff --git a/src/plugins/border.js b/src/plugins/border.js
index 130e1ae4..1a3159f3 100644
--- a/src/plugins/border.js
+++ b/src/plugins/border.js
@@ -1,43 +1,62 @@
-const handleWidth = ({ configValue, important }) => {
-  const value = configValue('borderWidth')
-  if (!value) return
+const borderWidthConfig = [
+  {
+    property: 'borderTopWidth',
+    value: regex => regex(/(?<=(border-t(-|$)))([^]*)/),
+  },
+  {
+    property: 'borderRightWidth',
+    value: regex => regex(/(?<=(border-r(-|$)))([^]*)/),
+  },
+  {
+    property: 'borderBottomWidth',
+    value: regex => regex(/(?<=(border-b(-|$)))([^]*)/),
+  },
+  {
+    property: 'borderLeftWidth',
+    value: regex => regex(/(?<=(border-l(-|$)))([^]*)/),
+  },
+  {
+    property: 'borderWidth',
+    value: regex => regex(/(?<=(border(-|$)))([^]*)/),
+  },
+]
 
-  return {
-    borderWidth: `${value}${important}`,
-  }
-}
+const borderColorConfig = [
+  { matchStart: 'border-t', property: 'borderTopColor' },
+  { matchStart: 'border-r', property: 'borderRightColor' },
+  { matchStart: 'border-b', property: 'borderBottomColor' },
+  { matchStart: 'border-l', property: 'borderLeftColor' },
+  { matchStart: 'border', property: 'borderColor' },
+]
 
-const handleColor = ({ toColor }) => {
-  const common = {
-    matchStart: 'border',
-    property: 'borderColor',
-    configSearch: 'borderColor',
-  }
-  return toColor([
-    { ...common, opacityVariable: '--tw-border-opacity' },
-    common,
-  ])
-}
+const getCommonColorConfig = ({ matchStart, property }) => ({
+  matchStart,
+  property,
+  configSearch: 'borderColor',
+})
 
 export default properties => {
   const {
-    match,
-    theme,
-    getConfigValue,
+    matchConfigValue,
     toColor,
     pieces: { important },
     errors: { errorSuggestions },
   } = properties
 
-  const width = handleWidth({
-    configValue: config =>
-      getConfigValue(theme(config), match(/(?<=(border-))([^]*)/)),
-    important,
-  })
-  if (width) return width
+  const getBorderWidthByRegex = regex => matchConfigValue('borderWidth', regex)
+  for (const task of borderWidthConfig) {
+    const value = task.value(getBorderWidthByRegex)
+    if (value) return { [task.property]: `${value}${important}` }
+  }
 
-  const color = handleColor({ toColor })
-  if (color) return color
+  for (const task of borderColorConfig) {
+    const common = getCommonColorConfig(task)
+    const value = toColor([
+      { ...common, opacityVariable: '--tw-border-opacity' },
+      common,
+    ])
+    if (value) return value
+  }
 
   errorSuggestions({ config: ['borderColor', 'borderWidth'] })
 }