The Best Vintage Men Styles For Fall/Winter 2021

  As the heat of summer dwindles down, and colder weather approaches, it is time to start breaking out the long pants, hats, and jackets to dress for the coming frigid seasons.

image for article The Best Vintage Men Styles For Fall/Winter 2021

As the heat of summer dwindles down, and colder weather approaches, it is time to start breaking out the long pants, hats, and jackets to dress for the coming frigid seasons. Sometimes we walk into stores and just feel like we see the same lifeless winter coats over and over.

However, with vintage clothes, it’s possible to remain comfortable, warm, and have an utterly unique style all through the fall and winter. 

The best part of shopping vintage is that the style options are practically endless. There is plenty of variety in the ways to style vintage clothes, especially for those approaching colder days. 

Read on to learn about our favorite vintage styles to wear this upcoming fall and winter season. 

Find a Reliable Jacket

The most crucial piece of the fall and winter uniform is a good, reliable jacket. Luckily, there is no shortage of stylish vintage coats and jackets readily available, so the next step is to find the style of jacket that works best for you and your individual style. 

There are all kinds of jacket styles, so in order to find the perfect jacket for you, it is important to weigh your options.

Below are some of our favorite kinds of vintage jackets to consider.

A Vintage Jean Jacket

Jean jackets are classic and will therefore never be out of style. Denim is always a great choice because it matches with most things and can be dressed up or down. To dress up the denim jacket, pair it with tweed pants and suede loafers. For a more casual day, throw on your favorite band tee and sunglasses.

Another positive about vintage denim jackets is that they can come in a variety of styles. Denim jackets might be lined with flannel or leather, they might have patchwork on them, and they can even come in a variety of colors, like black or gray. If the denim look is for you, there are plenty of great options to explore. 

Blazers and Sports Jackets

This fall and winter, you might want to opt for a more fancy attire; or perhaps you are looking to channel the 1860 Duke of Norfolk, who originated the sports jacket (the original influencer). Either way, you will look amazing this winter season donning a vintage sports jacket. 

Like any other kind of jacket, there is a wide variety of colors to choose from. For a bolder look, you might consider a sports jacket with a beige checkered pattern or remain classic with a solid color.

In addition to colors, play with lapel widths to channel different vintage eras every time. 

Leather Jackets

Another great option to look stylish this fall and winter is to find yourself a vintage leather jacket. Leather jackets are bulky and warm while maintaining that classic, vintage look. It is a great way to look stylish in the colder weather, and there is an abundance of vintage leather jackets ready to find a home. Leather jackets can range from the ‘40s era of aviation to ‘90s grunge. 

You do not have to limit yourself to just the kind of jackets listed above. The different styles are endless. Find a jacket that best compliments your style, and you’ll be well on your way to looking amazing this winter and fall. 

Sweater Weather

Colder weather means it is officially sweater weather (and no, not the 2013 hit song by The Neighborhood). ‘Tis the season to bundle up, but one of the best ways to remain warm and stylish is by grabbing a vintage sweater or two. 

Sweaters are a very versatile article of clothing. They can be worn casually, practically, or fancily. Regardless of the kind of style you have, there will be a vintage sweater to match your fashion sense. 


Cardigan sweaters are a wonderful option for those who tend to dress more classically. A solid-colored cardigan can be dressed up with a blazer or sport coat or worn more casually around the house.

But even if you have a more eclectic style, there is still a cardigan for you. Pick up a red cardigan to honor everyone’s favorite TV dad, Mr. Rogers, or a letterman sweater to channel Grease vibes.

Vintage Prints

Vintage print sweaters, in general, are a great way to make your style a little more playful as the weather gets colder. For instance, a crewneck sweater with geometric patterns is a great option if you want to wear more neutral colors but play around with patterns. 

Or perhaps you are into loud patterns and bright colors. Then, you might consider wearing a ’90s V-neck sweater with a cacophony of bright colors and abstract patterns. 

Cable Knit

For the most frigid days, the best kind of sweater to own is a thick cable knit sweater. Originating in Ireland, cable knit sweaters are designed to withstand rough weather but can also serve to be a fashionable statement piece in your wardrobe. Owning a vintage cable knit sweater will keep you warm and prepared for the harsh winter climate while maintaining a great sense of fashion. 

Sweaters are an integral part of the chilly weather attire, so find yourself a few vintage sweaters, and you’ll be warm and stylish this autumn and winter. 

Boots For The Season

Once cold weather approaches, it is time to retire the sandals and sneakers and bust out a pair of boots to wear. Boots are a necessity, especially if you live in a climate with regular snowfall. Though wearing boots is a matter of practicality, you can still remain stylish while dressing sensibly for the weather with these vintage styles. 

One of the more iconic boot styles, especially for snowy climates, are duck boots. Duck boots have a rubber sole to protect the feet from any precipitation one might encounter while still being comfortable and stylish. They go with anything and are extremely practical, so snag a vintage pair of duck boots for this winter season. 

Hiking boots are another practical but subtly stylish option to consider. Like duck boots, they serve a practical purpose as they protect the feet from any inclement weather but come in a variety of colors, sizes, and even patterns. Though they are best suited for a more casual look, they are a great choice of shoewear for chilly weather. 

Black vintage combat boots can also be a fun winter look. They will keep your feet warm and protected, they match with most things, and they just look very cool. It can be an extra fun challenge to add them to a more formal look to let out just a little bit of rebellion. 

Look Cool and Stay Warm

With these vintage styles, it has never been easier to look fashionable and be practical for the season. Check out Thrilling for a great variety of vintage jackets, sweaters, shoes, and more to accompany your personal style, sourced from the best indie businesses.

Being practical and stylish is more than possible with these vintage styles. Bundle up and shop vintage this fall and winter season.


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