How do I sort strings alphabetically while accounting for value when a string is numeric?

Pass a custom comparer into OrderBy. Enumerable.OrderBy will let you specify any comparer you like.

This is one way to do that:

void Main()
{
    string[] things = new string[] { "paul", "bob", "lauren", "007", "90", "101"};

    foreach (var thing in things.OrderBy(x => x, new SemiNumericComparer()))
    {    
        Console.WriteLine(thing);
    }
}


public class SemiNumericComparer: IComparer<string>
{
    /// <summary>
    /// Method to determine if a string is a number
    /// </summary>
    /// <param name="value">String to test</param>
    /// <returns>True if numeric</returns>
    public static bool IsNumeric(string value)
    {
        return int.TryParse(value, out _);
    }

    /// <inheritdoc />
    public int Compare(string s1, string s2)
    {
        const int S1GreaterThanS2 = 1;
        const int S2GreaterThanS1 = -1;

        var IsNumeric1 = IsNumeric(s1);
        var IsNumeric2 = IsNumeric(s2);

        if (IsNumeric1 && IsNumeric2)
        {
            var i1 = Convert.ToInt32(s1);
            var i2 = Convert.ToInt32(s2);

            if (i1 > i2)
            {
                return S1GreaterThanS2;
            }

            if (i1 < i2)
            {
                return S2GreaterThanS1;
            }

            return 0;
        }

        if (IsNumeric1)
        {
            return S2GreaterThanS1;
        }

        if (IsNumeric2)
        {
            return S1GreaterThanS2;
        }

        return string.Compare(s1, s2, true, CultureInfo.InvariantCulture);
    }
}

Just pad with zeroes to the same length:

int maxlen = sizes.Max(x => x.Length);
var result = sizes.OrderBy(x => x.PadLeft(maxlen, '0'));

And, how about this ...

string[] sizes = new string[] { "105", "101", "102", "103", "90" };

var size = from x in sizes
           orderby x.Length, x
           select x;

foreach (var p in size)
{
    Console.WriteLine(p);
}