Como classificar uma coluna por dados de outra coluna no JTable

Outra opção é criar um JTableque contenha uma Filecópia de cada coluna de dados. Dessa forma, você precisaria alterar o TableCellRendererpara exibir o tipo de arquivo, nome do arquivo ou data de criação do arquivo a partir do Filedependendo da coluna, mas os comparadores para cada coluna seriam capazes de obter o tipo de arquivo e a data de criação do arquivo a partir do Fileao mesmo tempo.

import java.awt.*;
import java.io.File;
import java.io.IOException;
import java.nio.file.Files;
import java.nio.file.attribute.BasicFileAttributes;
import java.nio.file.attribute.FileTime;
import java.text.DateFormat;
import java.text.SimpleDateFormat;
import java.util.Arrays;
import java.util.Collections;
import java.util.Comparator;
import java.util.List;
import java.util.Optional;
import javax.swing.*;
import javax.swing.table.DefaultTableCellRenderer;
import javax.swing.table.DefaultTableModel;
import javax.swing.table.TableModel;
import javax.swing.table.TableRowSorter;

public class GroupDirectoriesFirstComparatorTest {
  private Component makeUI() {
    String[] columnNames = {"Type", "Filename", "Date"};
    DefaultTableModel model = new DefaultTableModel(columnNames, 0) {
      @Override
      public Class<?> getColumnClass(int column) {
        return File.class;
      }
    };
    JTable table = new JTable(model);
    table.setAutoCreateRowSorter(true);
    table.setDefaultRenderer(File.class, new FileCellRenderer());
    RowSorter<? extends TableModel> sorter = table.getRowSorter();
    if (sorter instanceof TableRowSorter) {
      TableRowSorter<? extends TableModel> rs =
          (TableRowSorter<? extends TableModel>) sorter;
      for (int i = 0; i < model.getColumnCount(); i++) {
        rs.setComparator(i, new GroupDirectoriesFirstComparator(table, i));
      }
    }
    JButton button = new JButton("Choose directory");
    button.addActionListener(e -> {
      JFileChooser chooser = new JFileChooser();
      chooser.setFileSelectionMode(JFileChooser.DIRECTORIES_ONLY);
      int ret = chooser.showOpenDialog(button.getRootPane());
      if (ret == JFileChooser.APPROVE_OPTION) {
        model.setRowCount(0);
        File[] files = chooser.getSelectedFile().listFiles();
        if (files != null) {
          Arrays.stream(files)
              .map(f -> Collections.nCopies(3, f).toArray())
              .forEach(model::addRow);
        }
      }
    });
    JPanel p = new JPanel(new BorderLayout());
    p.add(new JScrollPane(table));
    p.add(button, BorderLayout.SOUTH);
    return p;
  }

  public static void main(String[] args) {
    EventQueue.invokeLater(() -> {
      JFrame frame = new JFrame();
      frame.setDefaultCloseOperation(WindowConstants.EXIT_ON_CLOSE);
      frame.getContentPane().add(
          new GroupDirectoriesFirstComparatorTest().makeUI());
      frame.pack();
      frame.setLocationRelativeTo(null);
      frame.setVisible(true);
    });
  }
}

class FileCellRenderer extends DefaultTableCellRenderer {
  private final DateFormat dateFormat = new SimpleDateFormat("yyyy.MM.dd");

  @Override
  public Component getTableCellRendererComponent(
      JTable table, Object value,
      boolean isSelected, boolean hasFocus,
      int row, int column) {
    Component c = super.getTableCellRendererComponent(
        table, value, isSelected, hasFocus, row, column);
    if (c instanceof JLabel && value instanceof File) {
      JLabel l = (JLabel) c;
      l.setHorizontalAlignment(LEFT);
      File file = (File) value;
      switch (table.convertColumnIndexToModel(column)) {
        case 0:
          l.setText(file.isDirectory() ? "DIRECTORY" : "FILE");
          break;
        case 1:
          l.setText(file.getName());
          break;
        case 2:
          l.setHorizontalAlignment(RIGHT);
          try {
            BasicFileAttributes attr =
                Files.readAttributes(file.toPath(), BasicFileAttributes.class);
            l.setText(dateFormat.format(attr.creationTime().toMillis()));
          } catch (IOException e) {
            throw new RuntimeException(e);
          }
          break;
        default:
          break;
      }
    }
    return c;
  }
}

class FileComparator implements Comparator<File> {
  private final int column;

  public FileComparator(int column) {
    this.column = column;
  }

  @Override
  public int compare(File a, File b) {
    switch (column) {
      case 0: return getWeight(a) - getWeight(b);
      case 2: return Long.compare(getCreationTime(a), getCreationTime(b));
      default: return a.getName().compareToIgnoreCase(b.getName());
    }
  }

  public int getColumn() {
    return column;
  }

  public static int getWeight(File file) {
    return file.isDirectory() ? 1 : 2;
  }

  public static Long getCreationTime(File file) {
    BasicFileAttributes attr;
    try {
      attr = Files.readAttributes(file.toPath(), BasicFileAttributes.class);
    } catch (IOException e) {
      throw new RuntimeException(e);
    }
    return Optional.ofNullable(attr)
        .map(BasicFileAttributes::creationTime)
        .map(FileTime::toMillis)
        .orElse(0L);
  }
}

// https://java-swing-tips.blogspot.com/2011/11/jtable-group-directories-first-sorting.html
class GroupDirectoriesFirstComparator extends FileComparator {
  private final JTable table;

  public GroupDirectoriesFirstComparator(JTable table, int column) {
    super(column);
    this.table = table;
  }

  @Override
  public int compare(File a, File b) {
    int v = getWeight(a) - getWeight(b);
    return v == 0 ? super.compare(a, b) : v * getSortOrderDirection();
  }

  private int getSortOrderDirection() {
    int dir = 1;
    List<? extends RowSorter.SortKey> keys = table.getRowSorter().getSortKeys();
    if (!keys.isEmpty()) {
      RowSorter.SortKey sortKey = keys.get(0);
      if (sortKey.getColumn() == getColumn() &&
          sortKey.getSortOrder() == SortOrder.DESCENDING) {
        dir = -1;
      }
    }
    return dir;
  }
}

Você precisa criar um comparador (deve ser uma classe não estática em ou com acesso ao seu modelo de tabela) para definir em seu RowSorter, como

class MyComparator implements Comparator<date> {
  if (row1.column1 = "DIRECTORY" && row2.column1 != "DIRECTORY) {
    return -1;
  }
  else if (row2.column1 == "DIRECTORY") {
    return 1;
  } else {
    return MyDateComparator.compareTo (row1.column4, row2.column4);
  }
}