Monday Musings: Tommy Hilfiger

“I’m a designer of more than clothes. I am a designer of a very creative concept.”
-Tommy Hilfiger

While Tommy Hilfiger has been considered one of the best American designers for men, his preppy and tailored looks for women are perfect for the upcoming holiday season. Read on for more fun facts and outfits inspired by this iconic American brand.

Some Fun Facts about Tommy Hilfiger

  • Tommy was born on March 24, 1951 and was raised in Elmira, New York.
  • He is the second of nine children, in an Irish Catholic family.
  • At the age of 25 Tommy’s first store, ‘People’s Place’ went bankrupt.
  • After this bankruptcy he was offered designing positions at for various brands, such as Calvin Klein, but declined.
  • He then founded the Tommy Hilfiger Corporation in 1984.
  • His clothes are aimed to be for the people, as the name of his first store suggests. The designs are well tailored and classic and have appealed to a large audience.
  • His Tommy line includes everything from clothes to fragrances, belts, beddings and cosmetics.


You want to look fashionable and put-together, not like you hit every sale rack this season.
-Tommy Hilfiger

Tommy Hilfiger Inspired
This is such a fun and cute winter look! Starting with some black tights, over the knee lace up boots, a khaki skirt, pink silk shirt and topped off with a red blazer. This look is very preppy and holiday inspired which is a signature of Tommy Hilfiger!
“One of the most important things to me is to make things real, not have models who are perfectly groomed or clothes that are too perfect. It all has to have a twist because that’s how people live.”
-Tommy Hilfiger

This look is perfect for the holiday season! The red dress just screams ‘I’m fun and festive!’ This dress is from Modcloth, and to channel the Tommy look pair it with black tights, a tan cape, tan lace up ankle booties and a Tommy tan scarf. This look is fun because the dress is super polished while the boots give a rugged edge.
“Women were wearing the men’s button-downs so I added men’s touches into women’s shirts. They’re basically the same – just sexier. They’re reshaped to the female body.”- Tommy Hilfiger
This look is a fun way to wear sparkles or sequins in a casual, daytime way. The skirt mixes a variety of blue colors which adds a lot of dimension to the skirt, and channels snow in winter! For the top try an oxford button up shirt, with black tights and black lace up ankle booties. For accessories keep it simple, with light blue studs and blue purses.
Do you like Tommy Hilfiger’s preppy and cute looks? Which one is your favorite?

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