Anna Wintour’s Take On Valentine’s Day And Dating

Great gift ideas from the fashion icon herself

Editor-in-chief of Vogue magazine and fashion icon, Anna Wintour, gives some great gift advice along with her best and worst date stories in celebration of Valentine’s Day.

When it comes to Valentine’s Day gifts Wintour thinks if you’re in a new relationship then you should get them a gift that isn’t too serious and gives off a sense of humor. She suggests cooking them dinner and she recommends recipes from the cooking publication Bon Apetit with her personal favorite being the squash carbonara.

Looking for a gift for a long-term relationship Wintour suggests something that is a gift for both partners such as bracelets from Scosha, a handcrafted fine jewelry store in Brooklyn, or rings from the iconic New York fine jeweler, Tiffany & Co. If you’re looking for a more fashion-oriented gift she recommends matching sweaters from Loverboy which is designed by Charles Jeffrey from London or for those on a bigger budget she recommends Prada.

One successful Valentine’s Day gifts for men are tickets to a sporting event like football or golf. Wintour also says that you should focus on giving something that someone really wants but wouldn’t dare to try themselves, one of her friends always wanted to try tap dancing so she gifted her some lessons and her friend loved it.

Wintour says that the most romantic gift she’s ever received is from her daughter and daughter-in-law created beautiful wedding albums after both their weddings for her. Though she thinks that her choice wouldn’t qualify as being only “romantic,” but in her mind, they were very personal and thoughtful which is what made it so special for her.

Anna Wintour celebrates Valentine’s Day by revealing her best and worst dates. She says her best date was going to the theatre with her daughter or attending a tennis match with her son.

Now we get to the juicy part, Anna Wintour’s worst date ever. Back in the 1970s, Wintour was interested in this young man she knew who happened to be an activist writer which would lead to him often getting arrested or going to jail, also resulting in getting a lot of bad press and publicity for it.

It just so happens that at the time she was seeing this young man, Wintour’s father was the editor of a newspaper and never showed any interest in the men she dated but decided he wanted to the writer she was dating. Wintour says when they met for the first time it was an “uncomfortable exchange” but at the end of the meeting, her dad says to the young man, “I know you’re interested in politics. Would you like to go to America and cover the upcoming election campaigns?”

The young man didn’t want to pass on the opportunity and said yes, leaving the next day for the U.S. and Wintour never saw him again after that. Wintour thinks that her father was being cunning and most likely wanted to separate them.