How To Dress Vintage This Winter

December 1, 2022

Some would argue that it is easier to dress in a vintage style throughout winter, as you can add as many layers as you want and include vintage pieces from top to bottom. The vintage clothing men wear is often more likely to be outerwear such as harrington or monkey jackets, whereas women might choose vintage pieces such as pencil skirts or dresses which are better suited for summer. 

If you want to learn how to dress with flawless vintage style this winter, be sure to keep reading.

Use key vintage pieces to complete your look 

Dressing in a vintage style does not necessarily mean you have to buy a whole new wardrobe, it is possible to purchase a few carefully selected pieces that will give your look a polished, vintage aesthetic without breaking the bank. 

Especially for vintage mens clothing, choosing a nice harrington jacket or a classic parka coat will automatically give your look a vintage feel without being too obvious. The main benefit to these jackets is that they can be worn over pretty much anything, already matching the majority of your wardrobe. Each coat sends a different message, so consider which vintage style you want to go for before you make a purchase. 

For example, a parka coat will give connotations of Oasis or The Beatles with its long khaki design and fishtail detailing at the back. A bomber jacket will reference the skinhead culture in the 60’s, and look great with a pair of straight leg jeans and Dr Martens boots. 

A Crombie coat is a great choice for those who want to look smart and have a look they can wear for all sorts of formal occasions. The long length and dark appearance add a sense of mystery and authority, a vintage style that is very popular among men even in the modern day. 

Shop at reputable vintage stores

When looking to purchase vintage clothing, it is important to choose a vendor who is either selling high quality garments or second hand, authentic vintage pieces.

There are plenty of high street stores who have been replicating original vintage styles for decades, but these are often of low quality and do not create the same look that authentic items do. 

For example, bomber jackets have been adopted by high street retailers and adapted to all sorts of shapes and styles, often losing their original shape and made using different materials. As a result, the jacket does not carry a vintage aesthetic look and will not achieve the style you are after. 

Refer to vintage style icons

If you do not currently have any vintage items in your wardrobe and are not sure where to start, referring to the style icons of the 60s and 70s is a great way to decide on your favourite styles so you can make purchases around that. 

Perhaps the most iconic of all is The Beatles, who created a whole new style of their own in the 1960s. John Lennon was famous for having his car covered in a paisley print, and the whole group were known for wearing paisley suits and accessories. They often covered up with long khaki fishtail parkas, a piece which is still popular today. 

Another band that helped revive mod culture are The Who, famous for pairing jeans with desert boots and redefining the union jack for young people who were adapting a more liberal identity. 

Do not forget to shop second hand for authentic vintage items

One way to wear authentic vintage clothes, often at a better price and less cost to the environment is to shop second hand. For items such as leather jackets, which can cost thousands of pounds when bought new, buying second hand is a great way to get beautiful, quality pieces that look even better than new designs.

While jackets are often found in second hand stores, jeans are another great item to thrift. When purchased new, Levi’s Jeans are often hundreds of pounds due to their high quality and world-renowned reputation, but these can often be found in second hand stores for a fraction of the price. These trousers are a staple in every vintage-lovers wardrobe and will make any outfit seem well-polished and retro. 

Another great item to buy when searching for vintage clothing for men and women are cardigans. Before hoodies and sweatshirts were popular, cardigans were a great way to keep warm and add an extra layer to your outfit and are very reminiscent of fashion in the 1900s. Vintage style cardigans made with real wool, as opposed to polyester pieces you might find in high street stores today, are much better for keeping you warm in the winter as well as better for the environment. 


In the summer, vintage style can be as simple as throwing on a polo shirt with some jeans and boots, or choosing a floral or paisley shirt. In the winter, you can layer to your heart’s content, starting with a smart vintage jacket all the way down to your shoes. The best thing about vintage clothing for men is that it is wearable year after year, and you need only buy one or two pieces each season to top up your wardrobe. Simple, stylish and high quality, there is no doubt that vintage is the only style that never goes out of fashion. 

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Andi Perullo de Ledesma

I am Andi Perullo de Ledesma, a Chinese Medicine Doctor and Travel Photojournalist in Charlotte, NC. I am also wife to Lucas and mother to Joaquín. Follow us as we explore life and the world one beautiful adventure at a time.

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