dennisdoomen · dennisdoomen · Sep 5, 2026 · Sep 5, 2026 · Sep 5, 2026
diff --git a/Pathy.ApiVerificationTests/ApprovedApi/pathy.net47.verified.txt b/Pathy.ApiVerificationTests/ApprovedApi/pathy.net47.verified.txt
@@ -4,7 +4,7 @@ namespace Pathy
     [System.ComponentModel.TypeConverter(typeof(Pathy.ChainablePathTypeConverter))]
     [System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
     [System.Text.Json.Serialization.JsonConverter(typeof(Pathy.ChainablePathJsonConverter))]
-    public readonly struct ChainablePath : System.IEquatable<Pathy.ChainablePath>, System.IFormattable
+    public readonly struct ChainablePath : System.IComparable, System.IComparable<Pathy.ChainablePath>, System.IEquatable<Pathy.ChainablePath>, System.IFormattable
     {
         public Pathy.ChainablePath Directory { get; }
         public bool DirectoryExists { get; }
@@ -26,6 +26,8 @@ namespace Pathy
         public static Pathy.ChainablePath New { get; }
         public static Pathy.ChainablePath Null { get; }
         public static Pathy.ChainablePath Temp { get; }
+        public int CompareTo(Pathy.ChainablePath other) { }
+        public int CompareTo(object? obj) { }
         public Pathy.ChainablePath FindParentWithFileMatching(params string[] wildcards) { }
         public bool HasExtension(string extension) { }
         public bool HasName(string name) { }
@@ -46,6 +48,10 @@ namespace Pathy
         public static Pathy.ChainablePath operator +(Pathy.ChainablePath leftPath, string additionalPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, string subPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath? leftPath, string subPath) { }
+        public static bool operator <(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator <=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
     }
     public static class ChainablePathExtensions
     {
@@ -70,6 +76,15 @@ namespace Pathy
         public override object? ConvertFrom(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object value) { }
         public override object? ConvertTo(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object? value, System.Type destinationType) { }
     }
+    public sealed class PathComparer : System.Collections.Generic.IComparer<Pathy.ChainablePath>, System.Collections.Generic.IEqualityComparer<Pathy.ChainablePath>
+    {
+        public static Pathy.PathComparer Default { get; }
+        public static Pathy.PathComparer Ordinal { get; }
+        public static Pathy.PathComparer OrdinalIgnoreCase { get; }
+        public int Compare(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public bool Equals(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public int GetHashCode(Pathy.ChainablePath obj) { }
+    }
     public static class StringExtensions
     {
         public static Pathy.ChainablePath ToPath(this string path) { }

diff --git a/Pathy.ApiVerificationTests/ApprovedApi/pathy.net8.0.verified.txt b/Pathy.ApiVerificationTests/ApprovedApi/pathy.net8.0.verified.txt
@@ -4,7 +4,7 @@ namespace Pathy
     [System.ComponentModel.TypeConverter(typeof(Pathy.ChainablePathTypeConverter))]
     [System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
     [System.Text.Json.Serialization.JsonConverter(typeof(Pathy.ChainablePathJsonConverter))]
-    public readonly struct ChainablePath : System.IEquatable<Pathy.ChainablePath>, System.IFormattable, System.ISpanFormattable
+    public readonly struct ChainablePath : System.IComparable, System.IComparable<Pathy.ChainablePath>, System.IEquatable<Pathy.ChainablePath>, System.IFormattable, System.ISpanFormattable
     {
         public Pathy.ChainablePath Directory { get; }
         public bool DirectoryExists { get; }
@@ -27,6 +27,8 @@ namespace Pathy
         public static Pathy.ChainablePath Null { get; }
         public static Pathy.ChainablePath Temp { get; }
         public Pathy.ChainablePath AsRelativeTo(Pathy.ChainablePath basePath) { }
+        public int CompareTo(Pathy.ChainablePath other) { }
+        public int CompareTo(object? obj) { }
         public Pathy.ChainablePath FindParentWithFileMatching(params string[] wildcards) { }
         public bool HasExtension(string extension) { }
         public bool HasName(string name) { }
@@ -49,6 +51,10 @@ namespace Pathy
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, System.Range range) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, string subPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath? leftPath, string subPath) { }
+        public static bool operator <(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator <=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
     }
     public static class ChainablePathExtensions
     {
@@ -73,6 +79,15 @@ namespace Pathy
         public override object? ConvertFrom(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object value) { }
         public override object? ConvertTo(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object? value, System.Type destinationType) { }
     }
+    public sealed class PathComparer : System.Collections.Generic.IComparer<Pathy.ChainablePath>, System.Collections.Generic.IEqualityComparer<Pathy.ChainablePath>
+    {
+        public static Pathy.PathComparer Default { get; }
+        public static Pathy.PathComparer Ordinal { get; }
+        public static Pathy.PathComparer OrdinalIgnoreCase { get; }
+        public int Compare(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public bool Equals(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public int GetHashCode(Pathy.ChainablePath obj) { }
+    }
     public static class StringExtensions
     {
         public static Pathy.ChainablePath ToPath(this string path) { }

diff --git a/Pathy.ApiVerificationTests/ApprovedApi/pathy.netstandard2.0.verified.txt b/Pathy.ApiVerificationTests/ApprovedApi/pathy.netstandard2.0.verified.txt
@@ -4,7 +4,7 @@ namespace Pathy
     [System.ComponentModel.TypeConverter(typeof(Pathy.ChainablePathTypeConverter))]
     [System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
     [System.Text.Json.Serialization.JsonConverter(typeof(Pathy.ChainablePathJsonConverter))]
-    public readonly struct ChainablePath : System.IEquatable<Pathy.ChainablePath>, System.IFormattable
+    public readonly struct ChainablePath : System.IComparable, System.IComparable<Pathy.ChainablePath>, System.IEquatable<Pathy.ChainablePath>, System.IFormattable
     {
         public Pathy.ChainablePath Directory { get; }
         public bool DirectoryExists { get; }
@@ -26,6 +26,8 @@ namespace Pathy
         public static Pathy.ChainablePath New { get; }
         public static Pathy.ChainablePath Null { get; }
         public static Pathy.ChainablePath Temp { get; }
+        public int CompareTo(Pathy.ChainablePath other) { }
+        public int CompareTo(object? obj) { }
         public Pathy.ChainablePath FindParentWithFileMatching(params string[] wildcards) { }
         public bool HasExtension(string extension) { }
         public bool HasName(string name) { }
@@ -46,6 +48,10 @@ namespace Pathy
         public static Pathy.ChainablePath operator +(Pathy.ChainablePath leftPath, string additionalPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, string subPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath? leftPath, string subPath) { }
+        public static bool operator <(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator <=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
     }
     public static class ChainablePathExtensions
     {
@@ -70,6 +76,15 @@ namespace Pathy
         public override object? ConvertFrom(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object value) { }
         public override object? ConvertTo(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object? value, System.Type destinationType) { }
     }
+    public sealed class PathComparer : System.Collections.Generic.IComparer<Pathy.ChainablePath>, System.Collections.Generic.IEqualityComparer<Pathy.ChainablePath>
+    {
+        public static Pathy.PathComparer Default { get; }
+        public static Pathy.PathComparer Ordinal { get; }
+        public static Pathy.PathComparer OrdinalIgnoreCase { get; }
+        public int Compare(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public bool Equals(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public int GetHashCode(Pathy.ChainablePath obj) { }
+    }
     public static class StringExtensions
     {
         public static Pathy.ChainablePath ToPath(this string path) { }

diff --git a/Pathy.ApiVerificationTests/ApprovedApi/pathy.netstandard2.1.verified.txt b/Pathy.ApiVerificationTests/ApprovedApi/pathy.netstandard2.1.verified.txt
@@ -4,7 +4,7 @@ namespace Pathy
     [System.ComponentModel.TypeConverter(typeof(Pathy.ChainablePathTypeConverter))]
     [System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
     [System.Text.Json.Serialization.JsonConverter(typeof(Pathy.ChainablePathJsonConverter))]
-    public readonly struct ChainablePath : System.IEquatable<Pathy.ChainablePath>, System.IFormattable
+    public readonly struct ChainablePath : System.IComparable, System.IComparable<Pathy.ChainablePath>, System.IEquatable<Pathy.ChainablePath>, System.IFormattable
     {
         public Pathy.ChainablePath Directory { get; }
         public bool DirectoryExists { get; }
@@ -27,6 +27,8 @@ namespace Pathy
         public static Pathy.ChainablePath Null { get; }
         public static Pathy.ChainablePath Temp { get; }
         public Pathy.ChainablePath AsRelativeTo(Pathy.ChainablePath basePath) { }
+        public int CompareTo(Pathy.ChainablePath other) { }
+        public int CompareTo(object? obj) { }
         public Pathy.ChainablePath FindParentWithFileMatching(params string[] wildcards) { }
         public bool HasExtension(string extension) { }
         public bool HasName(string name) { }
@@ -48,6 +50,10 @@ namespace Pathy
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, System.Range range) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath leftPath, string subPath) { }
         public static Pathy.ChainablePath operator /(Pathy.ChainablePath? leftPath, string subPath) { }
+        public static bool operator <(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator <=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
+        public static bool operator >=(Pathy.ChainablePath left, Pathy.ChainablePath right) { }
     }
     public static class ChainablePathExtensions
     {
@@ -72,6 +78,15 @@ namespace Pathy
         public override object? ConvertFrom(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object value) { }
         public override object? ConvertTo(System.ComponentModel.ITypeDescriptorContext? context, System.Globalization.CultureInfo? culture, object? value, System.Type destinationType) { }
     }
+    public sealed class PathComparer : System.Collections.Generic.IComparer<Pathy.ChainablePath>, System.Collections.Generic.IEqualityComparer<Pathy.ChainablePath>
+    {
+        public static Pathy.PathComparer Default { get; }
+        public static Pathy.PathComparer Ordinal { get; }
+        public static Pathy.PathComparer OrdinalIgnoreCase { get; }
+        public int Compare(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public bool Equals(Pathy.ChainablePath x, Pathy.ChainablePath y) { }
+        public int GetHashCode(Pathy.ChainablePath obj) { }
+    }
     public static class StringExtensions
     {
         public static Pathy.ChainablePath ToPath(this string path) { }

diff --git a/Pathy.Specs/ChainablePathSpecs.cs b/Pathy.Specs/ChainablePathSpecs.cs
@@ -1,6 +1,8 @@
 using System;
+using System.Collections.Generic;
 using System.Globalization;
 using System.IO;
+using System.Linq;
 using System.Reflection;
 using FluentAssertions;
 using Xunit;
@@ -33,6 +35,33 @@ public void Can_build_from_an_absolute_path()
         path.IsRooted.Should().BeTrue();
     }
 
+    [Fact]
+    public void Can_sort_paths_by_segments()
+    {
+        var paths = new[]
+        {
+            ChainablePath.From("a/b/c"),
+            ChainablePath.From("a-b"),
+            ChainablePath.From("a/b")
+        };
+
+        paths.OrderBy(path => path, PathComparer.Ordinal).Should().Equal(
+            ChainablePath.From("a/b"),
+            ChainablePath.From("a/b/c"),
+            ChainablePath.From("a-b"));
+    }
+
+    [Fact]
+    public void Can_compare_paths_with_an_explicit_case_policy()
+    {
+        var upper = ChainablePath.From("folder/File.txt");
+        var lower = ChainablePath.From("folder/file.txt");
+
+        PathComparer.Ordinal.Equals(upper, lower).Should().BeFalse();
+        PathComparer.OrdinalIgnoreCase.Equals(upper, lower).Should().BeTrue();
+        new SortedSet<ChainablePath>(new[] { upper, lower }, PathComparer.OrdinalIgnoreCase).Should().ContainSingle();
+    }
+
     [Fact]
     public void Can_build_from_a_string()
     {

diff --git a/Pathy/ChainablePath.cs b/Pathy/ChainablePath.cs
@@ -27,7 +27,7 @@ namespace Pathy
     [JsonConverter(typeof(ChainablePathJsonConverter))]
 #endif
     [global::System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
-    public readonly record struct ChainablePath : IFormattable, ISpanFormattable
+    public readonly record struct ChainablePath : IFormattable, ISpanFormattable, IComparable<ChainablePath>, IComparable
 #else
     [global::Microsoft.CodeAnalysis.Embedded]
     [global::System.Diagnostics.DebuggerNonUserCode]
@@ -36,7 +36,7 @@ namespace Pathy
     [JsonConverter(typeof(ChainablePathJsonConverter))]
 #endif
     [global::System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
-    internal readonly record struct ChainablePath : IFormattable, ISpanFormattable
+    internal readonly record struct ChainablePath : IFormattable, ISpanFormattable, IComparable<ChainablePath>, IComparable
 #endif
 #else
 #if PATHY_PUBLIC
@@ -45,7 +45,7 @@ namespace Pathy
     [JsonConverter(typeof(ChainablePathJsonConverter))]
 #endif
     [global::System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
-    public readonly record struct ChainablePath : IFormattable
+    public readonly record struct ChainablePath : IFormattable, IComparable<ChainablePath>, IComparable
 #else
     [global::Microsoft.CodeAnalysis.Embedded]
     [global::System.Diagnostics.DebuggerNonUserCode]
@@ -54,7 +54,7 @@ namespace Pathy
     [JsonConverter(typeof(ChainablePathJsonConverter))]
 #endif
     [global::System.Diagnostics.DebuggerDisplay("{DebuggerDisplayValue,nq}")]
-    internal readonly record struct ChainablePath : IFormattable
+    internal readonly record struct ChainablePath : IFormattable, IComparable<ChainablePath>, IComparable
 #endif
 #endif
     {
@@ -357,6 +357,52 @@ private static bool EndsInDirectorySeparator(string path)
             return From(leftPath.ToString() + additionalPath);
         }
 
+        /// <summary>
+        /// Compares two paths using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public int CompareTo(ChainablePath other)
+        {
+            return PathComparer.Default.Compare(this, other);
+        }
+
+        /// <summary>
+        /// Compares this path with another object using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public int CompareTo(object? obj)
+        {
+            if (obj is null)
+            {
+                return 1;
+            }
+
+            if (obj is ChainablePath other)
+            {
+                return CompareTo(other);
+            }
+
+            throw new ArgumentException($"Object must be of type {nameof(ChainablePath)}", nameof(obj));
+        }
+
+        /// <summary>
+        /// Determines whether one path sorts before another using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public static bool operator <(ChainablePath left, ChainablePath right) => left.CompareTo(right) < 0;
+
+        /// <summary>
+        /// Determines whether one path sorts after another using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public static bool operator >(ChainablePath left, ChainablePath right) => left.CompareTo(right) > 0;
+
+        /// <summary>
+        /// Determines whether one path sorts before or equal to another using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public static bool operator <=(ChainablePath left, ChainablePath right) => left.CompareTo(right) <= 0;
+
+        /// <summary>
+        /// Determines whether one path sorts after or equal to another using <see cref="PathComparer.Default"/>.
+        /// </summary>
+        public static bool operator >=(ChainablePath left, ChainablePath right) => left.CompareTo(right) >= 0;
+
         /// <summary>
         /// Gets a value indicating whether the current <see cref="ChainablePath"/> instance is equal to <see cref="ChainablePath.Null"/>.
         /// </summary>

diff --git a/Pathy/PathComparer.cs b/Pathy/PathComparer.cs
@@ -0,0 +1,74 @@
+using System;
+using System.Collections.Generic;
+
+namespace Pathy;
+
+/// <summary>
+/// Compares paths by their individual segments.
+/// </summary>
+public sealed class PathComparer : IEqualityComparer<ChainablePath>, IComparer<ChainablePath>
+{
+    private readonly StringComparer segmentComparer;
+
+    private PathComparer(StringComparer segmentComparer)
+    {
+        this.segmentComparer = segmentComparer;
+    }
+
+    /// <summary>
+    /// Gets an ordinal, case-sensitive path comparer.
+    /// </summary>
+    public static PathComparer Ordinal { get; } = new(StringComparer.Ordinal);
+
+    /// <summary>
+    /// Gets an ordinal, case-insensitive path comparer.
+    /// </summary>
+    public static PathComparer OrdinalIgnoreCase { get; } = new(StringComparer.OrdinalIgnoreCase);
+
+    /// <summary>
+    /// Gets the platform default path comparer.
+    /// </summary>
+    public static PathComparer Default { get; } =
+#if NET5_0_OR_GREATER
+        OperatingSystem.IsWindows() ? OrdinalIgnoreCase : Ordinal;
+#else
+        Environment.OSVersion.Platform == PlatformID.Win32NT ? OrdinalIgnoreCase : Ordinal;
+#endif
+
+    /// <inheritdoc />
+    public int Compare(ChainablePath x, ChainablePath y)
+    {
+        string[] leftSegments = GetSegments(x);
+        string[] rightSegments = GetSegments(y);
+        int length = Math.Min(leftSegments.Length, rightSegments.Length);
+
+        for (int index = 0; index < length; index++)
+        {
+            int comparison = segmentComparer.Compare(leftSegments[index], rightSegments[index]);
+            if (comparison != 0)
+            {
+                return comparison;
+            }
+        }
+
+        return leftSegments.Length.CompareTo(rightSegments.Length);
+    }
+
+    /// <inheritdoc />
+    public bool Equals(ChainablePath x, ChainablePath y) => Compare(x, y) == 0;
+
+    /// <inheritdoc />
+    public int GetHashCode(ChainablePath obj)
+    {
+        int hash = 17;
+        foreach (string segment in GetSegments(obj))
+        {
+            hash = unchecked((hash * 31) + segmentComparer.GetHashCode(segment));
+        }
+
+        return hash;
+    }
+
+    private static string[] GetSegments(ChainablePath path) =>
+        path.ToString().Split(new[] { '/', '\\' }, StringSplitOptions.None);
+}