Rat Pack Fashion

Frank Sinatra’s style was equally as impressive as his singing and acting credits. The crooner knew how to dress and carry himself with the utmost confidence and class as only a true gentleman could. Perhaps one of the best eras of men’s fashion, revamp your wardrobe with these pieces that demand attention and bring some sophistication to modern day attire.


Was it a fedora or a trilby? Either way, Frank Sinatra knew how to wear a hat and it was undoubtedly his most hallmark style. According to Sinatra, it takes two hands to put on a hat the right way: the back brim should be curled up, and the front tugged down to a couple of inches above the right brow.

This Classico Wool Felt Fedora by brand Scala retails for $46 at Nordstrom.


Sinatra has been quoted many times saying that for him, “a tuxedo is a way of life,” and that every man should have one. Not just a rental for a wedding or black tie affair, invest in a tuxedo that is well-suited and well-fitted to your body’s size, shape and height. Make sure it is an appropriate color (black is always a safe bet), and that you pair it with a vest over a cummerbund.

Get this Hugo Boss Black Trim-Fit Tuxedo for $795 at Macy’s.

Three-piece suits

Three-piece suits come in a range of styles and cuts, but all include a jacket, vest and pants of the same material. Seersucker suits (which look like period pieces thanks to their prominent pastel colors), are popular in the summer, but it’s the dark or gray solid or plaid patterned three-piece suit that was worn often by men.

Try the Regent Fit Three-Piece Flannel 1818 Suit (on sale for $778) from Brooks Brothers on for size.


These days, unless you are going to a black tie affair or appearing as the groom at your own wedding, cufflinks seem to be a thing of the past. Bring them back, but with a classic style. Stay away from the tacky cartoon shapes and bright colors and don’t go over the top with big statement pieces. Instead, opt for sleek shapes like a circle or square in stainless steel, silver, gold plated or rhodium finishes.

These Gunmetal Square Tartan Cufflinks are available for $95 at www.cufflinks.com.

Silk ties and pocket squares

Ol’ Blue Eyes loved his ties. A fan of the conservative yet dapper silk tie, Sinatra also wore pocket squares with his suits as well (his favorite color was orange). The pocket square must be perfectly folded and should complement the tie it is paired with. Since today’s patterns are a bit more daring, it is OK to mix prints and solids, just keep it tasteful.

Pictured, the Debonair Solid tie in Royal Blue ($19) and the Persian Manor pocket square ($10) are both available at www.tiebar.com.

Check out more from LIW‘s Frank Sinatra theme issue:

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Anton Media Staff
In addition to its arts and entertainment publication Long Island Weekly, Anton Media Group publishes 16 community newspapers, several magazines, specialty publications and websites. With brands dating back to 1877, Anton has a commitment to deliver trusted and relevant content to the communities it serves.

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