diff --git a/pkg/controller/photo/edit_delete.go b/pkg/controller/photo/edit_delete.go
index 1f1affe..ee87457 100644
--- a/pkg/controller/photo/edit_delete.go
+++ b/pkg/controller/photo/edit_delete.go
@@ -76,6 +76,7 @@ func Edit() http.HandlerFunc {
 				altText    = strings.TrimSpace(r.FormValue("alt_text"))
 				isExplicit = r.FormValue("explicit") == "true"
 				isGallery  = r.FormValue("gallery") == "true"
+				isPinned   = r.FormValue("pinned") == "true"
 				visibility = models.PhotoVisibility(r.FormValue("visibility"))
 
 				// Profile pic fields
@@ -101,6 +102,7 @@ func Edit() http.HandlerFunc {
 				models.NewFieldDiff("Caption", photo.Caption, caption),
 				models.NewFieldDiff("Explicit", photo.Explicit, isExplicit),
 				models.NewFieldDiff("Gallery", photo.Gallery, isGallery),
+				models.NewFieldDiff("Pinned", photo.Pinned, isPinned),
 				models.NewFieldDiff("Visibility", photo.Visibility, visibility),
 			}
 
@@ -108,6 +110,7 @@ func Edit() http.HandlerFunc {
 			photo.AltText = altText
 			photo.Explicit = isExplicit
 			photo.Gallery = isGallery
+			photo.Pinned = isPinned
 			photo.Visibility = visibility
 
 			// Can not use a GIF as profile pic.
diff --git a/pkg/controller/photo/upload.go b/pkg/controller/photo/upload.go
index 17590c4..2595b61 100644
--- a/pkg/controller/photo/upload.go
+++ b/pkg/controller/photo/upload.go
@@ -66,6 +66,7 @@ func Upload() http.HandlerFunc {
 				isExplicit = r.PostFormValue("explicit") == "true"
 				visibility = r.PostFormValue("visibility")
 				isGallery  = r.PostFormValue("gallery") == "true"
+				isPinned   = r.PostFormValue("pinned") == "true"
 				cropCoords = r.PostFormValue("crop")
 				confirm1   = r.PostFormValue("confirm1") == "true"
 				confirm2   = r.PostFormValue("confirm2") == "true"
@@ -144,6 +145,7 @@ func Upload() http.HandlerFunc {
 				AltText:         altText,
 				Visibility:      models.PhotoVisibility(visibility),
 				Gallery:         isGallery,
+				Pinned:          isPinned,
 				Explicit:        isExplicit,
 			}
 
diff --git a/pkg/controller/photo/user_gallery.go b/pkg/controller/photo/user_gallery.go
index d233307..c380838 100644
--- a/pkg/controller/photo/user_gallery.go
+++ b/pkg/controller/photo/user_gallery.go
@@ -16,6 +16,7 @@ func UserPhotos() http.HandlerFunc {
 
 	// Whitelist for ordering options.
 	var sortWhitelist = []string{
+		"pinned desc nulls last, updated_at desc",
 		"created_at desc",
 		"created_at asc",
 	}
diff --git a/pkg/models/photo.go b/pkg/models/photo.go
index 973418f..0693b1b 100644
--- a/pkg/models/photo.go
+++ b/pkg/models/photo.go
@@ -24,6 +24,7 @@ type Photo struct {
 	Visibility      PhotoVisibility `gorm:"index"`
 	Gallery         bool            `gorm:"index"` // photo appears in the public gallery (if public)
 	Explicit        bool            `gorm:"index"` // is an explicit photo
+	Pinned          bool            `gorm:"index"` // user pins it to the front of their gallery
 	CreatedAt       time.Time       `gorm:"index"`
 	UpdatedAt       time.Time
 }
diff --git a/web/templates/photo/gallery.html b/web/templates/photo/gallery.html
index 72fdd25..c7d1733 100644
--- a/web/templates/photo/gallery.html
+++ b/web/templates/photo/gallery.html
@@ -19,6 +19,13 @@
     <small class="has-text-grey">Uploaded {{.CreatedAt.Format "Jan _2 2006 15:04:05"}}</small>
 </div>
 <div class="mt-2">
+    {{if .Pinned}}
+    <span class="tag is-success is-light">
+        <span class="icon"><i class="fa fa-thumbtack"></i></span>
+        <span>Pinned</span>
+    </span>
+    {{end}}
+
     {{if .Explicit}}
     <span class="tag is-danger is-light">
         <span class="icon"><i class="fa fa-fire"></i></span>
@@ -420,6 +427,11 @@
                                     <label class="label" for="sort">Sort by:</label>
                                     <div class="select is-fullwidth">
                                         <select id="sort" name="sort">
+                                            {{if not .IsSiteGallery}}
+                                            <option value="pinned desc nulls last, updated_at desc"{{if eq .Sort "pinned desc nulls last, updated_at desc"}} selected{{end}}>
+                                                Pinned, recently updated
+                                            </option>
+                                            {{end}}
                                             <option value="created_at desc"{{if eq .Sort "created_at desc"}} selected{{end}}>Most recent</option>
                                             <option value="created_at asc"{{if eq .Sort "created_at asc"}} selected{{end}}>Oldest first</option>
                                         </select>
diff --git a/web/templates/photo/upload.html b/web/templates/photo/upload.html
index 02c7fa8..a8cae92 100644
--- a/web/templates/photo/upload.html
+++ b/web/templates/photo/upload.html
@@ -260,6 +260,25 @@
                                 </p>
                             </div>
 
+                            <div class="field mb-5">
+                                <label class="label">
+                                    <i class="fa fa-thumbtack mr-1 has-text-success"></i>
+                                    Pinned Photo
+                                    <span class="tag is-success ml-2">New!</span>
+                                </label>
+                                <label class="checkbox">
+                                    <input type="checkbox"
+                                        name="pinned"
+                                        value="true"
+                                        {{if or (not .EditPhoto) (.EditPhoto.Pinned)}}checked{{end}}>
+                                    Keep this photo at the top of my gallery
+                                </label>
+                                <p class="help">
+                                    You may "pin" your favorite photos to keep them always at the front of
+                                    your photo gallery.
+                                </p>
+                            </div>
+
                             <div class="field mb-5">
                                 <label class="label">Photo Visibility</label>
                                 <div>