Vintage Wonderland: How to Rock A Retro Look This Winter

Vintage Wonderland: How to Rock A Retro Look This Winter

If you're looking for a unique way to stand out this winter, why not try rocking a retro look? Vintage fashion is making a comeback, and it’s the perfect way to make a statement this season. From classic silhouettes to bold prints, there are countless ways to incorporate vintage-inspired styles into your everyday wardrobe. In this article, we'll explore how to rock a retro look this winter, from tips on sourcing vintage pieces to styling advice. Read on to learn how to make a vintage fashion statement this season.

Winter is well underway, bringing all of the traditional cold weather and holiday cheer along with it. Now is the time of year when t-shirts and shorts have been packed away, making room for sweaters and flannel jammies instead.

Don't worry though, just because it is too cold for your strappy sandals and sleeveless dresses doesn't mean you have to hang up your sense of fashion for the season. Winter is the perfect time to show off your collection of vintage apparel! Harken back to some of the most iconic looks of all time while keeping toasty warm this winter.

Katharine Hepburn Loved Wearing Slacks

Vintage Wonderland: How to Rock a Retro Look This Winter

Connecticut Historical Society

In the days when women's style was synonymous with skirts and dresses, Katherine Hepburn dared to be different by wearing slacks at almost every opportunity. She proved that you didn't need to wear a dress to look gorgeous; paired with the right blouse and killer shoes a pair of wide legged trousers could look just as glamorous as the most delicate ball gown.

Besides being incredibly comfortable, a pair of long pants is going to be infinitely warmer in the winter than any skirt! Pair a long-sleeved top with a pair of trousers under a full length coat to pay homage to the inadvertent style queen of the 30's and 40's.

Bogie's Iconic Trench Coat

How to Rock a Retro Look This Winter: Trench Coats


Everybody needs a fantastic coat to protect them from the cold and there is no coat more famous than Humphrey Bogart's classic trench coat. Made an indelible part of his image in Casablanca and The Maltese Falcon, you could no more picture Humphrey Bogart without his trench coat than you could picture Abe Lincoln without his stove pipe hat.

Take advantage of this historic look by pairing a trench coat with a classic pair of wing tips or, if you are feeling especially vintage, a fedora. A full-length trench coat is an amazing way to keep warm while evoking the feeling of a romantic melodrama while you are out and about in the snow.

Louise Brooks and Her Beret

Vintage Wonderland: How to Rock a Retro Look This Winter


If a hat is necessary to keep your head warm in the icy weather, why not wear something with a little bit of style? Silent film star Louise Brooks helped popularize several looks, including the bobbed haircut that became synonymous with the flapper. One of the looks that made it big because of her influence was the beret, a cap perfectly designed to keep her head warm while showing off her stylishly short hair.

If you are looking to frame an amazing bobbed 'do this winter you simply can't go wrong with a beret. Pair it with some smoky eye make-up and a set of pearls to complete that 1920's chic look.

Nancy Sinatra's Boots

How to Rock a Retro Look This Winter: Calf Boots are a Must!


If you want to keep your legs warm this winter you might consider walking in Nancy Sinatra's footsteps and putting on a pair of fabulous boots. In 1966 Nancy quickly became known the world over for her feminist message and her legendary calf-length boots, made famous by her song These Boots Are Made For Walking.

If you truly want that vintage Nancy Sinatra look, match the color of your boots to your outfit and throw on a pair of tights or sheer panty hose to complete the image. 

Jackie O. and her Pillbox Hat

Vintage Wonderland: Pillbox Hat and Tweed

The Telegraph

If ever there was a woman who understood the value of completing an outfit with a hat, it was Jaqueline Kennedy Onassis. Pairing a tweed jacket with a matching pillbox hat was so classically Jackie O. that they still make Halloween costumes of her based on that look! Always stylish and gorgeous, she was a fashion icon who inspired an entire generation of women's couture.

Topping off your winter wear with a pillbox hat is an excellent way to add a vintage twist to your look. If you want to be true to Jackie's style make sure to match your hat to your coat.

Lucille Ball's Hidden Pants

Vintage Wonderland: Pants under Dresses


From her feedbag dress turned runway look to her stint as the world's most sunburnt fashion model, television's Queen of Comedy was known as a bit of a fashionista. No matter what else she might have worn, slacks under a dress was a look that is quintessentially Lucy. In fact, when the Franklin Mint and Mattel made collectible Lucy figures, this was the outfit she was wearing! Known as the Hostess Set look, a gorgeous skirt gave the outfit a feeling of elegance while a pair of slacks underneath was the ultimate in comfort.

This seminal look was brought back in a big way at the 2016 Oscars by none other than Lady Gaga, so clearly this is a trend whose time has come again. If you want to put a bit of a modern spin on this look, consider a pair of leggings or yoga pants under a dress with a funky print.

What is your favorite vintage look this winter? Tell us in the comments below!

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About the Author

Rachael Brennan