Dress for Success: The Retro Look

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/)


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  • Thank for you this article. It’s good to see some focus put on lawyers’ dress. A few comments:

    I disagree with the notion that a DB suit is necessarily retro – they’re never really gobe away, but haven’t been popular as single breasted suits for at least half a century (with a small exception in the 80s with the Armani power suit look, as seen in American Psycho).

    I also disagree that a DB suit isn’t proper for portly men. This is an oft-cited “rule” that has little grounding in reality. Many larger men look great in DB suits or in three pieces; what matters is the cut of the suit.

    Regarding hats: don’t lump all brimmed hats under the category “fedora.” While some men look great in them, others loot better in a porkpie, or a trilby. For summer, a straw panama hat is likely your best choice to keep the sun away. Try on several different styles (The Art of Manliness has an excellent article on hat selection) to determine what you like best.

    Lastly, I’d be wary of whatever GQ has to say about men’s clothing. It’s a fashion magazine whose aim is to advertise for and sell whatever the latest trend in men’s clothing happens to be. Too often, their models in skin-tight pinned suits look absolutely ridiculous and wholly unsuited for the courtroom.

    If I might recommend, those men who wish to dress elegantly and classically should consider reading Alan Flusser’s “Dressing the Man” for some tips. Additionally, there are some excellent web resources out there, specifically Styleforum’s Men’s Clothing forum, which is devoted almost wholly to tailored menswear.

  • Love the comments about men’s style and secondhand shopping, and the comment about GQ. The fashion mags are fun but it’s important to keep in mind that their goal is to get you to buy, buy, buy.

    It’s refreshing to read what men who enjoy fashion have to say.

  • I love this post! Thank you for recognizing that a classic look for men is particularly classy and being aware of “dressing for success” goes a long way toward making an impression. Not only is it important for lawyers and other professionals to be educated about looking suave, but let’s don’t forget to educate our clients about how to dress in court. It never hurts to go above and beyond, and the nostalgic throwbacks of a fedora and pocket square not only polish a person’s look, but let others know that you are serious business and to be reckoned with. I commend you for your commendation of this look.

  • “Some suggestions in retro dressing for men: Suave 1930?s Gentleman look – Assemble a fedora hat, large necktie and drape cut London aristocratic suit together and you got it made at the office or during board meetings. John Travolta “Grease” look – a very simple casual assembly using tight jeans, tight t-shirt and a leather jacket. The icing on the cake is the well gelled hair to give a “greased hair” effect. Metal 80?s look – Sometimes called heavy metal fashion. All you need are ripped jeans and band t-shirts. You can add acid washed denim jackets with sunglasses as accessories. This is the classic punk rock look for guys.”

    • Wow, until you mentioned it, I never realized how much like a lawyer John Travolta’s look from Grease — or Brett Michaels’s look from his 80s Poison concerts — could be.