Some say that the television show "Mad Men" changed the world of style. Men started the millennium with a specific fashion sense. It was a little messy and a little rock n' roll. Then Don Draper appeared, looking like a more dapper version of your father, and men's fashion took on an entirely new character. Draper’s fedora has become an icon. On the show, it is often paired with well-tailored suits. Now it's memorialized in the Smithsonian's National Museum of American History along with other Mad Men costumes. Other characters personify 1960s fashion with distinctive hats.
Grab a cocktail and sit back as we deconstruct the hats of "Mad Men". These styles can upgrade your fashion sense or help you win a best costume nod at your next theme party.
Draper’s FedoraDon Draper sets the tone with his signature fedora hats. Throughout the series, he wears several different trilby hats. All of them are made from high-quality felt.
The pinched crown prevents the accessory from making his head look like a rectangle. The hat tapers at the top, mimicking the shape of Jon Hamm’s chin and strong jawline. This creates a balanced, symmetrical effect that highlights Draper’s meticulous grooming.
Draper’s hat brings back one of the most important rules of 1960s mens fashion. Instead of calling attention to itself, the hat accentuates his handsome face.
Roger Sterling’s fedora similarly calls attention to his striking features. However, Roger’s hat is a little rounder at the top, complementing his more delicate features. Whereas Draper wears brown or gray hats, Roger dresses in a black fedora. The stark color shows off his flashier
style. Draper and Sterling both wear their fedoras at a no-nonsense straight angle. They’re serious about their power and influence. If you want to look a little jauntier in a fedora, tilt it to the back or to the side. You’ll look a little more carefree.
Although Draper would never be caught dead in a newsboy cap, Jon Hamm is often photographed in flat caps. Now that he doesn’t have to keep up a clean-shaven appearance, the actor dons a hip look with a beard and a driving cap.
Peggy’s Pillbox HatThe women of Mad Men didn’t ignore one of the era’s most prominent accessories. Peggy’s signature style involved versions of cloche and pillbox hats. In the first episode, Peggy feels awkward in an elevator full of men. Perhaps it’s her awkward mustard-colored hat that chips away at her confidence.
Although some pillbox hats are so tiny that they’re considered fascinators, the one that Peggy wore on the show was more practical. In another elevator scene, Peggy wears a large white pillbox that wraps around her head. By the end of the series, Peggy transitions into 1970s fashion with her crocheted beanie and military-inspired dress.
The women in Sterling’s lives also sport the pillbox style from time to time. In season 2, episode 9, Sterling’s wife, Mona, wears a sleek silver version with a tidy bow to a dinner party. She sheds the pillbox for a dramatic black Audrey Hepburn hat when she visits her now-estranged husband to discuss their daughter’s wedding plans later in the series. By that time, their daughter, Margaret, has adopted the pillbox style.
Meghan’s Straw Sun HatDraper wears his suit and fedora at the pool in the season 4 finale, but Meghan shows her fresh, young side with a floppy sun hat. The crown is smoothly molded, and the wide, gracefully undulating brim frames her face perfectly.
She and Draper’s son both demonstrate that sun protection hasn’t changed much in the past 50 years. The bucket hat that Robert Draper wears in that episode is similar to the cotton sun hats worn by kids today. When she goes to Hawaii with Draper, Meghan also protects her skin with fashion in a white sun hat with a textured scalloped pattern.
How To Wear Mad Men HatsWhether you’re trying to upgrade your day-to-day look or putting together a costume, remember to choose a hat that gives prominence to your features. Do you want people to notice you or your hat?
The iconic mens hat styles from the series make you look a little mysterious. Paired with your everyday wardrobe, it can look more contemporary and less like a uniform from a particular decade. Grab a colorful pillbox to set off a modern preppy look. Throw on a straw sun hat to keep your skin from aging and show off your sprightly side. Wearing a hat can hide messy hair and make you look a little more elegant without changing your entire wardrobe.