When some things are gone, they are gone forever. See generally, pogs, Beanie Babies, and Arrested Development. But when it comes to fashion, the retro look is extremely popular right now. The double-breasted suit, pocket square, and fedora are all great pieces to have in your wardrobe. So step into this week’s Dress for Success to find out the best way to pull off these looks and unleash your inner Don Draper.

The Double-Breasted Suit

This suit is a classic look. Picture Humphrey Bogart in pretty much any movie, and you’re imagining the right look. Instead of the popular single-breasted suit, the double-breasted has the two sides of the jacket overlap. I have yet to see one of these suits worn properly in court. The people I see wearing them either have suits that are too big, too small, or just not properly tailored. But in the May issue of GQ, style writer Simon Spurr talks about this classic look. If you have the right body for it and the suit is properly tailored, these suits look good.

If you have a big stomach, this suit is not for you. Just move on and get a great looking two-button suit. The beauty of the double-breasted suit is that it really emphasizes your chest and shoulders. But in order to properly do that, the jacket has to be tailored snugly around the middle. Otherwise you will look like you are wearing your father’s hand-me-down. Spurr points out that a “double-breasted jacket should be shorter than a single-breasted. You should be able to see your crotch.” No need for the fingertip rule here. Keep it short and snug with well-fitting pants and you’ll successfully rock this classic look.

Pocket Squares

According to The Art of Manliness, a pocket square can add a touch of panache to really complete an outfit. I agree completely. The pocket square is a great opportunity to showcase your understanding of fashion by picking a color and pattern that goes with your suit, shirt, and tie to make the whole outfit come together.

To be clear, when I say “go with” I do not mean match. A pocket square should never identically match anything else on your person. I know what you’re thinking. You’ve seen those little boxes they sell with a tie, a pocket square, and cuff links that all have the exact same pattern. Those tend to be good deals. If it’s a fun pattern then go ahead and buy it. But never wear more than one item from that box at a time.

After you pick an appropriate pocket square, you need to learn how to fold it. Luckily, YouTube exists to walk you through the process. Now pop it in your jacket pocket and go wow a few people.


Hats used to be all the rage. Then John F. Kennedy, amongst others, stopped wearing hats and their popularity waned significantly. Fast forward almost fifty years and hats are making a resurgence. The fedora is particularly popular. You can wear a more formal cloth version, or a casual straw fedora for weekends or the golf course. Make sure the fedora fits properly. It should not come down over your ears, and it should not leave any red marks on your head from being too tight. When picking a style, go with something universal. Grey can work with pretty much any color suit, so it is the most versatile. Watch out for complex patterns around the rim. These can clash with the rest of your outfit if they are too bold.

Your fedora will look best if it’s cocked a little to one side and tipped forward slightly. It will look the worst if you put a feather in it. You’re not Robin Hood.

(photo: http://www.flickr.com/photos/momentsnotice/2863332595/)