Ask Alan - Spring 2007

We often hear about stylish stars from the past. Which of today’s celebrities and public figures best exemplify superior style?

This is a question that goes to the heart of what I term the “paradox of modern fashion.” If the likes of David Niven or Cary Grant are your style benchmarks, I’m afraid Hollywood’s current crop of leading males could not even tie their shoes. I cannot think of one contemporary movie star (or public personality, for that matter) whose tastes in clothes, on- or off-camera, projects either an individually transcendent or tutorially valuable sense of personal style. For me, the more provocative–and, therefore, more illuminating–question is, “Why?”

I like the look of a pocket square in suit jackets and sport coats, but I have no idea how to make it work for me. Any tips?

Anyone interested in male breast pocket decor has yet another reason to peruse my book–Dressing the Man: Mastering the Art of Permanent Fashion. There you’ll discover the mechanics of folding and wearing a pocket square. Here are some related thoughts:

1. The first step in pocket decor is learning how to wear a white, hand-rolled handkerchief well. It’s the least expensive way to give a mediocre suit a more expensive look.

2. Like a good haircut, the best-worn squares should not call attention to themselves. Don’t go overboard in an attempt to make a flashy statement.

3. While the necktie usually influences the choice of the pocket decor, the pocket square should never “match” anything–especially the tie.

4. The necktie and pocket square need to be related, but they shouldn’t be so studied that the eye bounces from one to the other, distracting all attention from the face. Winning combinations include a silk tie and linen hank; a solid necktie and a printed foulard; and a patterned necktie with a solid (or unsold) hank in one of the necktie’s colors.

5. Want to see pocket squares worn with aplomb? Look at old photos of Fred Astaire, Cary Grant, Gary Cooper and the Duke of Windsor.


–Taken from Menswear Magazine Spring 2007