Following the answer of @Even Mien I have tried to go a bit further and make it Generic, I seem to be almost there but one case still resist and I probably can simplify my code a bit.
I post it here if anyone see how I could improve and especially make it works as I can't assign it from a string

So Far I have the following results:

 Console.WriteLine(TestEnum.Test1);//displays "TEST1" bool test = "TEST1" == TestEnum.Test1; //true var test2 = TestEnum.Test1; //is TestEnum and has value string test3 = TestEnum.Test1; //test3 = "TEST1" var test4 = TestEnum.Test1 == TestEnum.Test2; //false //TestEnum test5 = "string"; DOESN'T compile .... :(:( 

Where the magics happens :

public abstract class EnumType<T> where T : EnumType<T> { public string Value { get; set; } protected EnumType(string value) { Value = value; } public static implicit operator EnumType<T>(string s) { if (All.Any(dt => dt.Value == s)) { Type t = typeof(T); ConstructorInfo ci = t.GetConstructor(BindingFlags.Instance | BindingFlags.NonPublic,null, new Type[] { typeof(string) }, null); return (T)ci.Invoke(new object[] {s}); } else { return null; } } public static implicit operator string(EnumType<T> dt) { return dt?.Value; } public static bool operator ==(EnumType<T> ct1, EnumType<T> ct2) { return (string)ct1 == (string)ct2; } public static bool operator !=(EnumType<T> ct1, EnumType<T> ct2) { return !(ct1 == ct2); } public override bool Equals(object obj) { try { return (string)obj == Value; } catch { return false; } } public override int GetHashCode() { return Value.GetHashCode(); } public static IEnumerable<T> All => typeof(T).GetProperties() .Where(p => p.PropertyType == typeof(T)) .Select(x => (T)x.GetValue(null, null)); } 

I only then have to declare this for my enums:

public class TestEnum : EnumType<TestEnum> { private TestEnum(string value) : base(value) {} public static TestEnum Test1 { get { return new TestEnum("TEST1"); } } public static TestEnum Test2 { get { return new TestEnum("TEST2"); } } }