How to Wear The Varsity Jackets With Style

How to Wear The Varsity Jackets With Style

Men’s letterman or if you prefer, varsity jackets, have come a long way since their origins as jocks’ sportswear in American high schools. So, we’re heading back to school for a lesson on how to style them.

Fashion Letterman Jackets

So, what’s changed since the 1930s? The basic elements are still there, but they’ve lost most of their practical function as representing your sporting prowess and allegiances. Fortunately for many of us, this means you don’t have to be a sporting god to wear one. Also, there are now more choices in style and color; some don’t even feature the bold traditional letters.

One of the main differences between traditional and modern varsity jackets is the material. You can still buy thick cotton jackets but they now also come in a wide variety of materials; leather, silk, nylon, suede, and so on. The move away from cotton means that most new varsity jackets have lost the heavy box silhouette.

The growing popularity of athleisure wear for men has resulted in the varsity jacket taking on many new styles and while more options are great; they also lead to a lot more fashion choices. Here’s a guide to different varsity jackets and how to wear them.

RELATED: How to Wear a Leather Jacket For Men In Style

How to Wear the Varsity Jacket Style

Men’s varsity jackets have become so popular though-out the years, to the point they even have their own style tribes. Here are a few to hopefully get you on the varsity bandwagon and find one that suits you.

Preppy Men’s Letterman Jacket Look

Got team spirit? Even if you don’t, the preppy look is a classic option for styling varsity jackets as it plays on their origins in US colleges. How preppy you decide to go is up to you but here are the best letterman designs for the look. Go for a jacket that plays up the varsity jacket’s unique points; the leather sleeves, contrasting cuffs, collar, and waistband, and, of course, choose one with a letter. Stick with the classic cotton body and avoid monotone jackets. Instead, try a bright color that’s more reminiscent of college colors and will stand out against the white leather sleeves.

Complete the look with a pair of classic chino pants, or if you’re really feeling preppy, why not try a colored or patterned trouser. This is easiest to pair with a navy varsity jacket because navy’s a very tonal color. If you go with brightly colored trousers choose a simple subtle top; a white shirt will keep the look crisp and preppy. Polos and plaid shirts will help you get the preppy look, plus you can layer up in winter with a thick woolen cardigan.

A preppy look consists of more than just black

Sporty Varsity Jacket Look

The sporty look is what the varsity jacket does best; it’s a great and very easy way to add a sporty, yet casual vibe to your outfit. A classic varsity jacket with all the key elements is one of the most wanted varsity jackets available. With a strong silhouette and choice of two colors, this jacket works well even if you don’t play any sports! You’ve just now got to figure out what to wear it with.

Like varsity jackets, joggers started as just sportswear but now have a firm place in men’s street style; making them the perfect combo. Joggers will keep the outfit casual and naturally have an ease about them that will make you look like you were born with style and just threw the outfit together. Dark or light joggers will work, but keep them simple and avoid bold patterns. Publish and Champion have a great selection to choose from.

To keep the look sporty, stick to basic T-shirts, or wear a casual sweatshirt. If you’ve gone for a brightly colored letterman, keep your top simple and go for a darker color that will balance out against the jacket. You can wear any color top with dark joggers, but if you’re wearing light-colored tracksuits go for a darker top or try a T-shirt with a pattern. Finish the look with some trainers or plimsolls.

Sporty Varsity Jacket Look

Color Matching Your Varsity Jacket

Now we’ve looked at the two key style tribes, it’s time to look at the different types of men’s varsity jackets. The easiest way to look at them is in color since there are so many different combinations on the market. Color matching your jacket is important as the jacket usually works as the focal point of your outfit

  • The Red and White Varsity Jacket For Men – This is probably one of the most iconic colorways of the varsity jacket. The red and white jacket easily blends into your wardrobe. Try wearing it with dark denim on the bottom, this means your jacket will be the statement piece.
  • The Blue Varsity Jacket (or Chelsea Varsity Jacket Style) – The blue varsity jacket is less common but looks great in the summer or through to spring. With this style, you can wear dark jeans or light blue jeans. Color matching an element of your trainers will anchor the style together.
  • The Black Varsity Jacket – The black varsity jacket is a fashion favorite. Usually made in leather or suede for the luxury market, it is a versatile piece. Just like any black jacket you can get away with wearing it with almost anything. However, a black jacket and a dark blue jeans combination are always a favorite.
  • The Black and Grey Varsity Jackets – Black and grey varsity jackets have been making their rounds on the blogs recently. They’re an updated version of the black leather jacket and are really easy to style.

Colour Matching You Varsity Jacket

Modern Street Style

More street than sport! Lots of modern varsity jackets are barely reminiscent of their sportswear predecessors and now have an edgier urban look that can be dressed up or left casual. Here’s how to get the look.

How to Wear The Varsity Jackets

If you’re going for a cool urban look, choose a simple black varsity jacket. Black is a popular color for modern letterman jackets as they have an edge to them that’ll give an urban vibe to an outfit. Keep your outfit slick with skinny black jeans, or alternatively, go for a looser-fitting look with some black chinos. Choosing trousers that crop at the ankle will give your outfit a modern look.

A white shirt is a great way to finish the look as it’s simple but contrasts against the dark varsity jacket and trousers. Alternatively, just throw on a simple T-shirt or jumper under your varsity jacket.

How to Wear a Leather Varsity Jacket

The black varsity is a must-have for your men’s wardrobe

READ: Men’s Dress Codes Guide For All Occasions


We all need a jacket that we can easily throw with anything when heading out to the pub, shops, or wherever we’re heading. You’ve hopefully caught on by now that varsity jackets basically go with everything and are really easy to style to suit your personal look, making them the ideal go-to casual jacket.

While you could go for a varsity jacket that has a distinctly preppy, sporty, or urban look; there are also a lot of simple letterman jackets out there that are super easy to throw on with jeans and a casual top. If you want a varsity jacket for all outfits, go for a darkly colored letterman. Navy or dark burgundy is a good choice for a casual varsity jacket.

History Of The Varsity Jacket

Let’s end this post with a quick history lesson. As the name would suggest, the varsity jacket came out of the American college system, specifically the prestigious Ivy League, Harvard University. Sports have always had a prominent place in American colleges and in 1865, Harvard decided they needed a way to distinguish their star baseball players from the rest of the student body. They did this by giving their top jocks a fabric letter ‘H’ to sew onto the center of their uniforms; hence the name letterman.

Initially, the honor of sporting the ‘H’ was strictly monitored and letters would be taken away if you didn’t maintain your standard of play. The best players were then allowed to keep the letter and wear it off-season and around campus.

A decade later, the ‘H’ was given to Harvard’s best football players, and slowly but surely other sports teams and universities caught on and created their own letterman jumpers. Each college played around with the positioning of the letter until most decided on the left breast where they are still placed today.

History Of The Letterman Jacket

letterman jacket history

The first varsity jacket wasn’t a jacket at all, but a jersey: a jumper or cardigan to Brits. It wasn’t until the 1930s that the letterman jacket actually became a jacket. Traditionally, the style has a wool body with contrasting leather sleeves, ribbed cuffs, collar, and waistband and would feature your school’s colors; think Andrew Clark in The Breakfast Club.

Over the twentieth century, fashion designers broke school rules and turned the classic varsity jacket into a more fashionable, and less elitist; a staple of modern menswear that could be worn by jock and nerds alike.

How to Wear The Varsity Jackets

  • Get the fit right, a lot of people go wrong with varsity jackets and end up looking swamped, as it’s a key piece you need to look good.
  • A preppy letterman jacket will have you looking smart and casual so keep it neat and sharp.
  • If sporty is more your thing, you need to make the outfit look easy like you’ve thrown it together.
  • Street Style and letterman jackets go hand in hand so keep it simple; simple designs, and simple colors.

The Best Men's Varsity Jackets And How To Style Them

Varsity jackets may be over 150 years old but they’ve never been so fashionable or stylish. While many designer brands have kept the iconic elements of the classic jackets; others have abandoned their historical roots and updated them for the twenty-first-century guy. If you’re after the preppy look, definitely go for an old-school style letterman with leather sleeves and ribbed collar and cuffs. However, if you want a more sporty or urban look, choose one that has a simpler design and go for dark colors. You may not be a sports star in your letterman, but at least you’ll be the most stylish guy out there.

Stay up to date
Register now to get updates on promotions and coupons

Shopping cart