How to Wear a Letterman Jacket?

When it comes to styling Letterman jackets, there are numerous options available, depending on personal preference and the occasion. The classic varsity look is always a safe bet—you can achieve it by pairing the jacket with jeans or chinos and a simple T-shirt or polo. For a more casual streetwear vibe, opt for distressed jeans and sneakers, or consider swapping the traditional jacket for a bomber-style version. Adding extra layers like a hoodie or flannel shirt brings depth and texture to the outfit.

What is Letterman Jacket?

Let's start by clarifying the proper name of this piece. Thanks to a Harvard baseball coach, sweaters worn by the team's best players began featuring the school's initial sewn onto them. Eventually, these sweaters evolved into jackets — hence the name: “Letterman” (from the English words letter and man), also known as varsity jackets or baseball jackets.

The Letterman jacket is a key element of the preppy and athletic (especially baseball-inspired) style. It's a bold statement piece that can easily anchor a stylish outfit, even when paired with the most basic wardrobe staples.

Despite its many names, the overall look of the jacket has remained virtually unchanged for decades. It's still a short, high-contrast jacket typically made of thick wool with leather sleeves, a relaxed fit, and snap-button closures. The signature detail? A large chenille letter or number on the left chest — plush, oversized, and instantly recognizable.

This is already a piece of history.

It all began in 1865. The letter "H" (for Harvard) was a mark of distinction, signifying that a player had achieved notable success on the university's baseball team. At first, the letter was sewn onto sweaters issued to all team members — but only the top players were allowed to keep them.

Everyone else had to return their sweaters to the coach at the end of the season. Other schools soon adopted this tradition, and it expanded beyond baseball to include other sports.

Eventually, Harvard's football team followed suit, embroidering the letter “H” on their uniforms. Players who took part in major games — particularly high-stakes matches against Yale and Princeton — were allowed to keep their sweaters. And so, an unofficial club of Letterman sweater holders was born.

The Transition to the Modern Look

In 1930, a major shift in the tradition occurred. Sweaters were replaced by jackets — and from that moment on, the design has remained largely unchanged: a wool body, leather sleeves, snap buttons, and large varsity letters. Additional insignia were sometimes stitched over the chest letters or even on the back.

The reason behind this transformation was simple: athletes needed warmer outerwear for playing in colder weather. Around this time, a new name for the garment emerged — the Varsity Jacket.

The tradition gained momentum and soon spread throughout all the Ivy League universities — America's most prestigious institutions: Harvard, Yale, Princeton, Cornell, Columbia, Brown, the University of Pennsylvania, and Dartmouth College. Over time, the Varsity Jacket found its way into the wardrobe of nearly every student-athlete across the United States.

The Fashion of the Letterman – Varsity Jacket

Over time, varsity jackets gained popularity far beyond the walls of schools and universities. The trend slowly made its way into mainstream pop culture. By the 1980s, you no longer had to be part of a sports team to wear one.

The jacket became a staple of fashion trends in both America and Europe. One of its most iconic moments came in Michael Jackson's music video for Thriller, where he wore a bright red varsity jacket with gold sleeves and a large embroidered “M.”

The Letterman jacket even made its way into the wardrobe of Princess Diana. In 1991, she was spotted wearing a silver and green varsity jacket from the Philadelphia Eagles — a gift from Jack Edelstein, the team's former stat manager and a friend of Grace Kelly.

Today, the varsity jacket has not lost its relevance. The Letterman remains a global fashion favorite, with fans including celebrities like Kanye West, Drake, Justin Bieber, and Jay-Z.

How to Wear Your Old Lettermans Jacket?

Classic Collegiate Style

Letterman jackets have been around for over a century and are more popular than ever. Originally created for high school and college athletes to showcase their achievements, these iconic jackets have evolved into a fashionable staple for style-conscious individuals.

If you're wondering how to best wear a Letterman jacket, we've got you covered. Here are a few tips on how to style this classic piece in different ways:

1. Classic Collegiate Style

The classic collegiate style is the most common way to wear a Letterman jacket. This look typically pairs the jacket with jeans or chinos, a simple T-shirt or button-down shirt, and sneakers. The jacket itself usually features a wool body, leather sleeves, and a large chenille letter patch on the chest representing the wearer's school or team.

To complete the look, you can add a beanie or baseball cap depending on your personal style. This outfit is perfect for casual outings or game-day events where you want to show off your team spirit.

2. Streetwear Style

Another popular way to style a Letterman jacket is by incorporating it into a streetwear look. This outfit pairs the jacket with more modern pieces like joggers, oversized hoodies, and high-top sneakers. The key to nailing this style is choosing a Letterman jacket with a contemporary twist—think slimmer cuts, bold color blocking, or unique detailing.

This style is perfect for those who lean toward trendier looks and want to make a fashion statement. It's ideal for concerts, casual hangouts, or just turning heads on the street.

3. Preppy Style

For those who prefer a preppy aesthetic, a Letterman jacket can easily fit into this polished look. Pair the jacket with slim-fit chinos, a collared shirt, and loafers or boat shoes. Opt for a Letterman jacket in more subdued colors like navy or black to maintain a refined appearance. You can also add a tie or bow tie to elevate the outfit further.

This style is perfect for semi-formal events such as weddings, graduations, or any occasion where you want to look sharp while still embracing a sporty edge.

4. Athleisure Style

The athleisure trend has been going strong for years, and a Letterman jacket fits right in. To achieve this look, pair your jacket with athletic wear like leggings, yoga pants, or joggers. Finish it off with a pair of clean sneakers, and you're good to go.

This style is perfect for running errands, heading to the gym, or just enjoying a relaxed evening out. It's all about comfort with a sporty, fashionable twist.

5. Layered Style

Layering is a great way to add visual interest to any outfit, and Letterman jackets work perfectly in a layered look. Start with a simple T-shirt or sweater, add a button-down shirt, and top it off with your Letterman jacket. You can also throw on a scarf or a beanie to add even more depth and personality.

This style is ideal for fall or winter when the temperature starts to drop. It's also a great option for those who enjoy playing with textures and patterns.

In conclusion, Letterman jackets are incredibly versatile pieces that can be styled in many different ways. Whether you lean toward a classic collegiate look, a streetwear vibe, or a polished aesthetic, there's a way to make a Letterman jacket work for you. So go ahead—experiment with different styles until you find the one that best reflects your personality and taste.

Vintage and Retro Outfits

If you're a fan of vintage and retro fashion, then Letterman jackets will definitely become an essential piece in your wardrobe. These jackets have been around since the 1800s and continue to be popular today, especially among those who love classic American style.

If you're wondering how to style Letterman jackets, you'll be glad to know there are plenty of ways to do it. Here are some vintage and retro outfit ideas that will look great with your Letterman jacket:

1. Rockabilly Look

The rockabilly style is a vintage vibe perfect for those who love rock 'n' roll. This look features bold prints, bright colors, and stylish accessories. To achieve it, pair your Letterman jacket with a graphic tee, high-waisted jeans, and Converse sneakers.

You can also add a bandana and cat-eye sunglasses to complete the outfit. This look is ideal for concerts or music festivals.

2. Hipster Look

The hipster look is a modern take on vintage fashion, perfect for those who want to look trendy and stylish. This style is all about mixing and matching different patterns, textures, and colors. To pull it off, wear your Letterman jacket with a plaid shirt, skinny jeans, and a pair of boots.

You can also add a beanie and a messenger bag to give the outfit a unique touch. This look is great for casual events like hanging out with friends.

In conclusion, Letterman jackets are versatile pieces that can be styled in many different ways. Whether you prefer a classic look, preppy style, rockabilly vibe, or hipster outfit, there's a style to suit your personality and taste. So don't be afraid to experiment with different outfits and have fun with your Letterman jacket!