This season’s outerwear trend is one of America’s best-loved fashion exports. From high school to high fashion, the iconic varsity jacket has been embraced by a variety of style subcultures over the years. And, now, it’s making a massive mainstream comeback.



What Is a Varsity Jacket?

Also known as the letterman, baseball or letter jacket, this effortlessly cool outerwear essential is sportier than the bomber jacket but preppier than the track jacket. Traditional designs feature two or more contrasting colours with a collarless, wool and button-through body and leather sleeves.

A Short History of the Varsity Jacket

The varsity jacket was first donned by young athletes in 1865, when the coach of Harvard University’s baseball team decided to reward his key players by emblazoning a huge letter ‘H’ on their woollen sweaters. Subsequently, dubbed ‘the letterman’, this wearable status symbol was later adopted by the university’s football team. The letterman soon became the sweater to be seen around campuses across America, with schools and colleges proudly branding both their elite male and female athletes with their prestigious initials.

In the early 1900s, these exclusive sweaters got an upgrade when the letterman sweater was joined by the more substantial letterman jacket. Both woollen garments were highly coveted in collegiate circles throughout the first half of the 20th century. By the 1950s, the varsity or letterman jacket had become a fashion must-have off-campus too, popularised by several icons of the era, including James Dean and Elvis Presley.

Varsity jackets in pop culture

By the 1980s, you no longer had to be an American jock to rock the varsity jacket. The letterman was embraced as a fashion staple on both sides of the Atlantic, rising to peak prominence when Michael Jackson donned an iconic red design for his infamous Thriller video

How are varsity jackets styled today by male celebrities

The classic varsity jacket remains a cult favourite amongst celebrities today, with contemporary artists such as Jay-Z, Kayne West, Drake, P Diddy, Justin Bieber and Zac Efron all recently pictured rocking varsity styles.

This season, however, the all-American uniform of high-school football players and their cheerleader girlfriends has been given a fashion makeover. For 2020, the versatile varsity jacket has a little less bulk and a little more structure, with flattering cuts and a range of stylishly muted pastel colourways to choose from. From sporty to preppy, retro to classic, here are our top tips for layering up with this season’s coolest jacket.

How to Wear a Varsity Jacket for Guys?

how to wear a varsity jacket men_letterman jacket guys

Go for a slim fit

Proving you no longer have to be a buff athlete to work the varsity jacket, today’s designs aren’t quite so bulky or overtly macho as yesteryear. Contemporary letterman jackets deliver a subtler, fitted and more flattering silhouette that pairs easily with a wider variety of trousers and bottoms. Shorter guys should still opt for a minimalist, slim fit design that won’t add disproportionate bulk to the upper half. Keep the balance with tapered or slim fit trousers, but add some punch with graphic stripes on the shoulders, cuffs or neckline.  

Choose a monochrome piece for an easier approach

If you’re new to the varsity trend, there’s no need to dive straight in with a flashy red Michael Jackson number. Stick to simple black and white designs for an understated jacket that won’t overwhelm the rest of your wardrobe and that can take you from day to night without any thought at all. For a casual yet stylish combo, layer your white varsity jacket over a plain grey or black tee, add a pair of distressed jeans and finish the look with some classic canvas kicks. Or, for a slimming, streamlined silhouette, keep your tee and jeans black and choose a varsity jacket with a black body and white or cream sleeves.

Try a varsity jacket in pastels to freshen up your look

Pastel tones are everywhere this season. And, with a varsity jacket in peachy pink or dusty lavender, you can easily combine two trends in the one outfit. These soft and extremely wearable tones will add a pop of contemporary colour to your wardrobe and will ensure your varsity jacket remains the main attraction of your outfit, but without overpowering it. Layer over a neutral-toned tee and combine with your favourite pair of distressed denim jeans.

Dress it down with denim and hi-top trainers

Modern varsity jackets in light greys, whites, creams and pastels work well with all shades of denim and make for a modest yet stylish look. These contemporary takes on the letterman classic have a softer and more relaxed vibe that’s best suited to daytime attire. Team with hi-top trainers in similar tones for a casual outfit that’ll become your go-to for match day, dinner dates or drinks at the pub.   

Dress it up with a shirt, tapered trousers and brogues

Keep it casual but classy with a monochrome or neutral-toned varsity jacket and layer over a crisp button-down on top, paired with tapered trousers down below. Smarten up your ensemble further by throwing a pair of classic brogues into the mix, and you’ll have an outfit that’s smart enough for the office but not too corporate to take to those after-work drinks.

What to Wear with a Varsity Jacket?

how to wear a varsity jacket men_letterman jacket guys


  • A white tee
  • Skinny black jeans
  • Chinos
  • High-top trainers

The varsity jacket and navy jeans combo is a classic pairing that’s stood the test of time. For a laidback look that’s right on trend this season, ditch the primary colours and choose a design in softer, pastel combos such as teal and white, peach and cream or lavender and grey. Pair with skinny black jeans or casual chinos and opt for simple, sporty footwear such as high tops, Converse or your favourite pair of trainers.


  • A graphic tee
  • Black jeans
  • A leather basketball cap
  • A metallic belt
  • Hi-top trainers

The varsity jacket really lends itself to the cool, urban aesthetic of modern streetwear. Go for sporty designs that evoke ’80s nostalgia and team with black jeans in relaxed or skinny fits. If you want to add a little extra edge, consider a varsity jacket design that features prominent embroidery in primary colours on the left breast, wrists or waist. Layer over a graphic tee and add a leather baseball cap, metallic belt or high-top sneakers for a look that’s both sporty and street. 

Smart casual

  • A button-down shirt
  • Charcoal grey or navy chinos
  • Gold accessories
  • Aviator sunglasses
  • Chelsea boots or monk strap shoes

Give your after-work outfit an edge by throwing a two-toned varsity jacket over your shirt and tie. Remember that the letterman jacket is casual by default, so balance it out with smart trousers underneath to avoid looking sloppy in the office. Choose a design in cool, monochrome colours, add a button-down shirt underneath and pair with charcoal grey or navy chinos. Dress it up with gold accessories, a pair of aviator shades and either smart Chelsea boots, leather double monks or a pair of white canvas low-tops.

Take-Home Message

how to wear a varsity jacket men_letterman jacket guys

The letterman jacket’s wide-reaching appeal has endured for an incredible 150 years. This fashion favourite owes much of its popularity to its ability to lend itself to a wide variety of outfits and occasions, pairing well with both casual separates and smart work pieces. Dress it up or down to achieve classic, urban or even slightly fancy looks this season. Whether your go-to look is sporty, retro or smart, the versatile varsity is once more the jacket to be seen in. 



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