diff --git a/picasso/src/main/java/com/squareup/picasso3/Picasso.kt b/picasso/src/main/java/com/squareup/picasso3/Picasso.kt
index b9a5abca68..50f1077534 100644
--- a/picasso/src/main/java/com/squareup/picasso3/Picasso.kt
+++ b/picasso/src/main/java/com/squareup/picasso3/Picasso.kt
@@ -97,6 +97,8 @@ class Picasso internal constructor(
   @get:JvmName("-targetToDeferredRequestCreator")
   internal val targetToDeferredRequestCreator = mutableMapOf<ImageView, DeferredRequestCreator>()
 
+  private val targetToSizeResolver = mutableMapOf<Any, SizeResolver>()
+
   @get:JvmName("-shutdown")
   @set:JvmName("-shutdown")
   internal var shutdown = false
@@ -135,6 +137,11 @@ class Picasso internal constructor(
     for (i in deferredRequestCreators.indices) {
       deferredRequestCreators[i].cancel()
     }
+
+    val sizeResolvers = targetToSizeResolver.values.toList()
+    for (i in sizeResolvers.indices) {
+      sizeResolvers[i].onCancel()
+    }
   }
 
   /** Cancel any existing requests for the specified target [ImageView]. */
@@ -181,6 +188,10 @@ class Picasso internal constructor(
         deferredRequestCreator.cancel()
       }
     }
+
+    targetToSizeResolver.values.forEach { sizeResolver ->
+      // TODO: Work out how to cancel size resolvers by tag.
+    }
   }
 
   @OnLifecycleEvent(ON_STOP)
@@ -200,6 +211,8 @@ class Picasso internal constructor(
         dispatcher.dispatchPauseTag(tag)
       }
     }
+
+    // TODO: Work how to to pause size resolvers.
   }
 
   /**
@@ -230,6 +243,8 @@ class Picasso internal constructor(
         dispatcher.dispatchResumeTag(tag)
       }
     }
+
+    // TODO: Work out how to resume size resolvers.
   }
 
   /**
@@ -386,6 +401,14 @@ class Picasso internal constructor(
     return nextRequest
   }
 
+  internal fun resolveSize(sizeResolver: SizeResolver, target: Any, callback: (Size) -> Unit) {
+    if (targetToSizeResolver.containsKey(target)) {
+      cancelExistingRequest(target)
+    }
+    targetToSizeResolver[target] = sizeResolver
+    sizeResolver.resolve(callback)
+  }
+
   @JvmName("-defer")
   internal fun defer(view: ImageView, request: DeferredRequestCreator) {
     // If there is already a deferred request, cancel it.
@@ -517,6 +540,7 @@ class Picasso internal constructor(
       action.cancel()
       dispatcher.dispatchCancel(action)
     }
+    targetToSizeResolver.remove(target)
     if (target is ImageView) {
       val deferredRequestCreator = targetToDeferredRequestCreator.remove(target)
       deferredRequestCreator?.cancel()
diff --git a/picasso/src/main/java/com/squareup/picasso3/RequestCreator.kt b/picasso/src/main/java/com/squareup/picasso3/RequestCreator.kt
index cb7edb7a30..95a470b358 100644
--- a/picasso/src/main/java/com/squareup/picasso3/RequestCreator.kt
+++ b/picasso/src/main/java/com/squareup/picasso3/RequestCreator.kt
@@ -58,6 +58,7 @@ class RequestCreator internal constructor(
   @DrawableRes private var errorResId = 0
   private var placeholderDrawable: Drawable? = null
   private var errorDrawable: Drawable? = null
+  private var sizeResolver: SizeResolver? = null
 
   /** Internal use only. Used by [DeferredRequestCreator].  */
   @get:JvmName("-tag")
@@ -68,6 +69,12 @@ class RequestCreator internal constructor(
     check(!picasso.shutdown) { "Picasso instance already shut down. Cannot submit new requests." }
   }
 
+  fun sizeResolver(sizeResolver: SizeResolver): RequestCreator {
+    check(!deferred) { "Use only one of fit() or sizeResolver()." }
+    this.sizeResolver = sizeResolver
+    return this
+  }
+
   /**
    * Explicitly opt-out to having a placeholder set when calling [into].
    *
@@ -433,6 +440,17 @@ class RequestCreator internal constructor(
       return
     }
 
+    if (sizeResolver != null) {
+      picasso.resolveSize(sizeResolver!!, target) { (width, height) ->
+        resize(width, height)
+        loadIntoTarget(target, started)
+      }
+    } else {
+      loadIntoTarget(target, started)
+    }
+  }
+
+  private fun loadIntoTarget(target: BitmapTarget, started: Long) {
     val request = createRequest(started)
     if (shouldReadFromMemoryCache(request.memoryPolicy)) {
       val bitmap = picasso.quickMemoryCacheCheck(request.key)
@@ -556,11 +574,18 @@ class RequestCreator internal constructor(
           setPlaceholder(target, getPlaceholderDrawable())
         }
         picasso.defer(target, DeferredRequestCreator(this, target, callback))
+        picasso.resolveSize(ViewSizeResolver(target), target) { (width, height) ->
+          data.resize(width, height)
+          loadIntoImageView(target, started, callback)
+        }
         return
       }
-      data.resize(width, height)
     }
 
+    loadIntoImageView(target, started, callback)
+  }
+
+  private fun loadIntoImageView(target: ImageView, started: Long, callback: Callback? = null) {
     val request = createRequest(started)
 
     if (shouldReadFromMemoryCache(request.memoryPolicy)) {
diff --git a/picasso/src/main/java/com/squareup/picasso3/ViewSizeResolver.kt b/picasso/src/main/java/com/squareup/picasso3/ViewSizeResolver.kt
new file mode 100644
index 0000000000..c0f2d8ac4b
--- /dev/null
+++ b/picasso/src/main/java/com/squareup/picasso3/ViewSizeResolver.kt
@@ -0,0 +1,74 @@
+package com.squareup.picasso3
+
+import android.view.View
+import android.view.ViewTreeObserver
+import androidx.annotation.Px
+
+interface SizeResolver {
+  fun resolve(listener: (Size) -> Unit)
+  fun onCancel()
+}
+
+data class Size(@Px val width: Int, @Px val height: Int)
+
+class ViewSizeResolver(
+  private val target: View,
+) : SizeResolver, ViewTreeObserver.OnPreDrawListener, View.OnAttachStateChangeListener {
+
+  private var listener: ((Size) -> Unit)? = null
+
+  override fun resolve(listener: (Size) -> Unit) {
+    val startingWidth = target.width
+    val startingHeight = target.height
+
+    if (startingWidth > 0 && startingHeight > 0) {
+      listener(Size(startingWidth, startingHeight))
+      return
+    }
+
+    this.listener = listener
+    target.addOnAttachStateChangeListener(this)
+    // Only add the pre-draw listener if the view is already attached.
+    // See: https://github.com/square/picasso/issues/1321
+    if (target.windowToken != null) {
+      onViewAttachedToWindow(target)
+    }
+  }
+
+  override fun onCancel() {
+    listener = null
+    target.removeOnAttachStateChangeListener(this)
+    val vto = target.viewTreeObserver
+    if (vto.isAlive) {
+      vto.removeOnPreDrawListener(this)
+    }
+  }
+
+  override fun onPreDraw(): Boolean {
+    val vto = target.viewTreeObserver
+    if (!vto.isAlive) {
+      return true
+    }
+
+    val width = target.width
+    val height = target.height
+
+    if (width <= 0 || height <= 0) {
+      return true
+    }
+
+    target.removeOnAttachStateChangeListener(this)
+    vto.removeOnPreDrawListener(this)
+    listener?.invoke(Size(width, height))
+    listener = null
+    return true
+  }
+
+  override fun onViewAttachedToWindow(view: View) {
+    view.viewTreeObserver.addOnPreDrawListener(this)
+  }
+
+  override fun onViewDetachedFromWindow(view: View) {
+    view.viewTreeObserver.removeOnPreDrawListener(this)
+  }
+}