Can I serialize nested properties to my class in one operation with Json.net?

You can do it with the following converter:

public class MyModelConverter : JsonConverter
{
    [ThreadStatic]
    static bool cannotWrite;

    // Disables the converter in a thread-safe manner.
    bool CannotWrite { get { return cannotWrite; } set { cannotWrite = value; } }

    public override bool CanWrite { get { return !CannotWrite; } }

    public override bool CanConvert(Type objectType)
    {
        return typeof(MyModel).IsAssignableFrom(objectType);
    }

    public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
    {
        var obj = JObject.Load(reader);
        obj.SelectToken("details.size").MoveTo(obj);
        obj.SelectToken("details.weight").MoveTo(obj);
        using (reader = obj.CreateReader())
        {
            // Using "populate" avoids infinite recursion.
            existingValue = (existingValue ?? new MyModel());
            serializer.Populate(reader, existingValue);
        }
        return existingValue;
    }

    public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
    {
        // Disabling writing prevents infinite recursion.
        using (new PushValue<bool>(true, () => CannotWrite, val => CannotWrite = val))
        {
            var obj = JObject.FromObject(value, serializer);
            var details = new JObject();
            obj.Add("details", details);

            obj["size"].MoveTo(details);
            obj["weight"].MoveTo(details);
            obj.WriteTo(writer);
        }
    }
}

public static class JsonExtensions
{
    public static void MoveTo(this JToken token, JObject newParent)
    {
        if (newParent == null)
            throw new ArgumentNullException();
        if (token != null)
        {
            if (token is JProperty)
            {
                token.Remove();
                newParent.Add(token);
            }
            else if (token.Parent is JProperty)
            {
                token.Parent.Remove();
                newParent.Add(token.Parent);
            }
            else
            {
                throw new InvalidOperationException();
            }
        }
    }
}

public struct PushValue<T> : IDisposable
{
    Action<T> setValue;
    T oldValue;

    public PushValue(T value, Func<T> getValue, Action<T> setValue)
    {
        if (getValue == null || setValue == null)
            throw new ArgumentNullException();
        this.setValue = setValue;
        this.oldValue = getValue();
        setValue(value);
    }

    #region IDisposable Members

    // By using a disposable struct we avoid the overhead of allocating and freeing an instance of a finalizable class.
    public void Dispose()
    {
        if (setValue != null)
            setValue(oldValue);
    }

    #endregion
}

And then use it like this:

[JsonConverter(typeof(MyModelConverter))]
public class MyModel
{
    [JsonProperty("name")]
    public string Name { get; set; }
    [JsonProperty("size")]
    public string[] Size { get; set; }
    [JsonProperty("weight")]
    public string Weight { get; set; }
}

public class TestClass
{
    public static void Test()
    {
        string json = @"{
            ""name"" : ""widget"",
            ""details"" : {
                ""size"" : [
                    ""XL"",""M"",""S"",
                ],
                ""weight"" : ""heavy""
            }
        }";
        var mod = JsonConvert.DeserializeObject<MyModel>(json);
        Debug.WriteLine(JsonConvert.SerializeObject(mod, Formatting.Indented));
    }
}

The ReadJson() method is straightforward: deserialize to a JObject, restructure the appropriate properties, then populate the MyModel class. WriteJson is a little more awkward; the converter needs to temporarily disable itself in a thread-safe manner to generate a “default” JObject that can be then restructured.