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Mad Men: The Main Characters’ Most Iconic Looks

Mad Men: The Main Characters' Most Iconic Looks

The characters in Mad Men were sharp dressers and their looks reflected their personalities, whether it was a bold, shapely dress or a grey suit.

Mad Men is one of the most stylish television shows of all time, and with all its slick suits and 60s dresses, the characters on the show really got to dress the part. While not every moment saw the characters looking their best, with Pete Campbell’s tennis shorts and Betty Draper’s infamous pink dressing gown reflecting this, for the most part, the characters always looked good.

Being set in the 1960s and running up to November 1970, the clothing that the characters wore was obviously all from this era. And while some of the outfits may not seem like the height of fashion now, some iconic pieces just can’t be forgotten by fans of the show.

Roger Sterling – His Blue Jacket

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Roger Sterling is one of the sharpest dressed characters throughout the series, always looking the part. He prides himself on looking good and this really makes him stand out as a character. He has some fantastic suits during the show’s run, but his blue jacket is his most iconic.

It’s something he wears quite a lot throughout the series, and it allows him to look good when he is out meeting different clients, attempting to secure business for the company. His sole job is to bring in business by taking them out for meals, therefore picking out a jacket like this simply allowed him to stand out from the start.

Megan Draper – Her Black Dress

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Megan Draper is a very stylish character, and she is someone who brings a slightly modern twist to her clothing in comparison to some of the other characters. This suited her personality as one of the younger people on the show, symbolizing the change she was ushering in as a character.

She wears some brilliant outfits throughout the series, but the best of the bunch was the black dress that she wore for Don’s birthday party. Megan went all out for the night and clearly wanted to look good for her husband, and considering her singing scene is so iconic, it only made this dress even more memorable. With the entire party being stunned at her appearance and Don showing no interest, it summed up their relationship in one outfit decision.

Sally Draper – Her Sparkly Dress

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Sally Draper was a fan of Megan and her style and she influenced the way Sally wanted to dress. Their relationship came at the time when Sally was growing up and she wanted to showcase this with a change in dress sense.

Sally wears some great outfits over the course of the series, but this is by far the most memorable and it really marks the turning point for her as a character, where she becomes more mature and starts to grow into a young adult.

Pete Campbell – His Blue Suit

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

While Roger Sterling might stand out wearing his blue jacket, he doesn’t go all the way with a full blue suit. This look is typically reserved for Pete Campbell, who often wears entirely blue numbers. This is a smart choice by the writers, as it allows Pete to look a little more modern than the rest of the characters.

He’s slightly younger than the rest of the main characters, and the fact he wears more modern colors showcases this. Pete aims to look as good as possible in order to impress, and his blue suits are the best way of doing that. He always wants to have an edge on everybody, and this color choice certainly provided that for him.

Joan Holloway – Her Red Dress

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Joan Holloway always looks great, and her fashion sense is a big part of her character. Joan always wears outfits to ensure she appears as professional as possible, while still looking good. Throughout the show, Joan wears some brilliant outfits, whether it’s at work or at social events.

Her most iconic look comes during an office Christmas party when she wears a form-fitting three-quarter length sleeved red dress that has her shining. She looks incredible in the dress and it certainly became a memorable style for her. The bold color makes her stand out and that is something she does throughout the show, which goes along with her confident personality.

Harry Crane – His Hollywood Look

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

At the start of the series, Harry Crane dresses like everyone else, in a normal suit and tie. However, once he forms the media role for himself, Harry decides to dress in far more eccentric suits in order to make a scene anytime he appears. Harry liked to think he was better than everybody else, and his outfits spoke to this.

He was very smug about his ability to meet different people in Hollywood, and he truly believed that he was ‘in’ with that crowd. The fact that he dressed so differently from everyone else at Sterling Cooper went along with his own self-inflated ego.

Bert Cooper – His Brown Tweed Suit

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Bert Cooper always dressed his very best, which is no surprise due to the fact he is one of the founding partners of Sterling Cooper. He has to look good as he is the boss, and throughout the show, he does, often wearing his brown or tweed suit to showcase his style.

His look is often a little more old-school with regards to the cut of his suit and the colors, to go along with his age. Of course, it never really mattered what Bert Cooper wore though, as the most iconic part of his look was the fact he never wore any shoes, and he always walked around in just socks. It’s part of his eccentric personality and added more mystery to his character, as well.

Betty Draper – Her Valentine’s Day Outfit

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Betty Draper is a very glamorous person who wears some fantastic outfits during the course of the show. Because she gets to attend a lot of events alongside Don, she wears some amazing dresses, but the best comes during her Valentine’s Day date with Don.

She makes a major entrance in this episode, as she walks down the stairs slowly revealing her stunning dress. Betty looks brilliant and it even takes Don back, reminding him exactly what he has for a brief moment. The dress worked perfectly here because it was Betty’s way of showcasing her beauty, making a point to her husband, and doing so on a Valentine’s Day date was the right time to do it.

Peggy Olson – Her Bold Outfit When She Left

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

Peggy Olson goes through the biggest change in character throughout the series, and while that’s clear in her personality, her style also changes a lot as well to reflect this. She learns to dress for the job and totally changes the type of clothes she wears from the start.

The most iconic of her outfits comes when she is strutting out of the office in total confidence with all of her belongings in a box, her sunglasses on, and a cigarette in her mouth. The outfit is sleek, bright, and looks fantastic with its bold primary colors. This new and empowered Peggy is a total contrast from the Peggy that starts the show, who was very timid.

Don Draper – His Classic Grey Suit

Mad Men: The Main Characters' Most Iconic Looks
Mad Men: The Main Characters’ Most Iconic Looks

When it comes to Don Draper, he always looks the part. It’s very rare that Don is shown with even a slight hair out of place, as he takes pride in his appearance, and a classic grey suit is his most iconic look. Sometimes, he will have a fedora hat on, depending on the location, and it was also a staple in his wardrobe.

Don wears a variety of suits throughout the show, as he has the finances to do so. However, a solid grey number is one that he often goes back to, and while it adapts as the show goes on in terms of design, it’s a color he uses the most. It’s a staple look for the time and something that was considered classic, which is very much in line with Don’s personality and how he presents himself to people. When looking at it deeper, grey is a muted color that blends in and doesn’t reveal much about one’s personality, which was in line with how Don lived his life with regards to the secrets he was keeping about his identity and his past.

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