How to Wear the Preppy Ivy League Style

How to Wear the Preppy Ivy League Style

February 13th, 2019

Without a doubt, the menswear trend of the season is the Ivy League look. From crisp tailoring to retro-inspired athletic pieces, the mid-century style is back in action. Think rugby shirts, coloured pants, stripes, and suede bombers.

You don’t have to be headed to college (or even college aged) to get the collegiate flair. We’ve blended preppy, nautical garden party style with the dressier New England approach for a refined, contemporary look that can be worn at any age. Here’s how to look the part.

3 ways to wear the Ivy League style

1. The Ivy League Alumnus

The blue blazer is the cornerstone of Ivy League style. Choose a sport jacket with soft shoulders and a mid-grey linen trouser for a relaxed silhouette, rather than the uptight vibe that can sometimes accompany the Ivy League outfits. This is the right look for the office or for dinner events.

Updated take: Rather than a solid blue or white shirt, opt for bold stripes. It freshens things up while staying true to the nautical theme. Short cropped trousers create an up-to-date silhouette.

2. The Game Day

Ralph Lauren’s iconic rugby shirt is an obvious choice here, with bold blue stripes and a crisp white collar.  The coral jeans are reminiscent of the GTH pants of the mid-20th century, and should be worn with gusto. Wear this to a garden party, lunch with the family, or for any of your weekend errands.

Updated take: A denim jacket over the rugby adds a layer of 2019 casual style to what is otherwise a quintessential ‘60s look.

3. The Saturday Suede

A suede bomber is a must-have for the season. When worn with a knit t-shirt or polo and light wash jeans, it takes on the preppy East Coast vibe while still maintaining the rugged bomber silhouette. This is a look that you can wear to patio parties, pub nights, coffee dates, or any casual event.

Updated take: While the boat shoe will always remain a classic, we chose a leather sneaker instead. Simple yet refined, it lends a more current style to this otherwise timeless outfit.


Ivy style will always be timeless, but we’re really looking forward to the more contemporary take that this season is bringing in. Make sure to tag us on Instagram if you decide to embrace the Ivy League look.

Easy Returns

We understand that things don't always work out. We offer easy returns in-store or by mail.

See it in-store

Come see the product up close at our Flagship Store.

Pickup in store

For local orders, in-store pickup is available for no cost.

Lifetime Service

Your clothing should always represent you well, whether you bought it yesterday or 5 years ago.

The Helm Clothing

The Flagship

Our brand new flagship store in Edmonton, Alberta is now open to serve you! In our mission to provide Edmonton with an elevated experience, our vision for this store was something spanning multiple floors with a unique experience on every level.