This article is an in-depth style guide to help you achieve that coveted American Ivy League Old Money look.
With over three decades of experience in the fashion industry, we’ve seen countless trends come and go, but the Ivy League style has remained a timeless classic.
So, let’s explore how you can incorporate this refined aesthetic into your wardrobe and elevate your style game.
American Ivy League Style Origins
The American Ivy League style is rooted in the early 1900s uniforms of prestigious Northeastern United States preparatory schools and universities, such as Harvard, Yale, and Princeton.
Inspired by traditional British preparatory school attire, this style has evolved into a conservative yet refined way of dressing that reflects the Preppy subculture’s elitism and affluent lifestyle.
It’s all about embracing classic pieces, paying attention to detail, and exuding an air of sophistication.
Ivy League Wardrobe Essentials
To nail the Ivy League look, you must understand the wardrobe essentials: clothing, footwear, and accessories.
Royal Navy Blazers
A three-button, single-breasted navy blazer is quintessential in any Ivy League wardrobe.
Opt for a well-fitted Old Money style blazer from brands like Brooks Brothers or Ralph Lauren for a polished appearance.
Wear it to corporate meetings, job interviews, or academic presentations to make a lasting impression.
Oxford Shirts (OCBD)
The American adaptation of the traditional British polo shirt, the Oxford shirt is made from thick cotton Oxford cloth and features a button-down collar.
Pair it with a blazer for a classic Ivy League ensemble, or wear it independently for a more casual look.
Brands like Gant, Tommy Hilfiger, and Ralph Lauren offer excellent office settings and business casual dinner options.
Chino Pants
Straight-legged, flat-front trousers made from twill fabric are a staple in the Ivy League style.
Look for a versatile and comfortable option for chinos from brands like J.Crew or Gant.
Wear them to business-casual office events, weekend errands, or family gatherings for a put-together appearance.
Penny Loafers
Slip-on leather shoes with a distinctive slot on the front and penny loafers are a must-have for any Ivy League enthusiast.
G.H. Bass and Sperry offer excellent options that will complement your outfit perfectly.
Wear them to academic settings, semi-formal dinners, or business-casual office environments to add a touch of sophistication to your look.
Cable-knit Sweater
Wool or cashmere sweaters woven in ‘cable’ patterns – a raised, textured surface – are available in V-neck and button-up cardigan styles.
Brands like Ralph Lauren and Lacoste offer high-quality options for layering over an Oxford shirt during autumn gatherings, casual Fridays, or holiday dinners.
American Ivy League Style Example
Michael, one of my clients, a young entrepreneur, was invited to a prestigious business conference.
We worked together to create an Old Money look inspired by the Ivy League to help him make a lasting impression at the event.
I got Michael to wear a perfectly tailored double-breasted navy blazer from Brooks Brothers, a crisp white Oxford shirt from Gant, khaki chinos from J.Crew, and a pair of brown penny loafers from G.H. Bass.
For an extra touch of original preppy style, I accessorised Michael’s Ivy League outfit with a subtle repp tie from Ralph Lauren.
The result was nothing less spectacular as Michael’s confidence (and look) landed him a significant business deal and many valuable connections.
Styling Tips
Having a well-curated selection of Ivy League staples in your wardrobe, you’ll be prepared for any event that comes your way.
However, you should consider some extra styling tips when infusing your Ivy League attire with a classic, old-money feel.
Occasion is Important
When crafting your Ivy League-inspired outfits, it’s crucial to consider the occasion.
While wearing a full double-breasted suit might be appropriate for a formal event or a job interview, you can opt for a more relaxed look for a casual Friday at the office or a weekend outing.
Fit is Critical
Ensure that your clothing fits well, as the Ivy League style is all about looking polished and put together.
Invest in tailoring to achieve the perfect fit, as ill-fitting clothes can ruin the overall aesthetic.
Wear a Classic Color Palette
Opt for neutral colours like navy, white, khaki, and olive green, with occasional pops of colour in your accessories.
This will help you create a versatile, timeless capsule wardrobe that exudes old-money sophistication.
Use Layering
Combine a blazer, Oxford shirt, and sweater for a sophisticated, multi-dimensional look.
This is especially effective during colder months or for more formal occasions.
Subtle Accessories
A repp tie, needlepoint belt, or argyle socks can add a touch of personality to your outfit without going overboard.
Brands like Brooks Brothers and Ralph Lauren offer accessories that perfectly complement the Ivy League style.
Wear Quality Clothes
The Ivy League style involves investing in high-quality, timeless pieces that will last for years to come.
Don’t be afraid to splurge on well-made garments from reputable brands.
They will form the foundation of your old-money wardrobe.
Style Like A True Gentleman
Before we say goodbye, here’s one of the best-kept secrets in men’s styling circles, a secret that only a few expert image consultants know or are willing to share.
First and foremost, professional styling requires knowing your unique body shape and seasonal colour palette – paramount factors in choosing perfectly fitting clothes in colours that complement your skin, eyes, and hair.
Only then can a stylist engage in styling by occasion, location, season, and time of day, with garments, footwear, and accessories from stylistically relevant heritage fashion brands to depict high confidence and success.
Best part? You can find your body shape, seasonal colour palette, and ideal fashion style in less than 5 minutes by yourself, for free, thanks to our four simple steps:
1. Find Your Body Shape
Different garments flatter different silhouettes, so knowing your body shape is the first step in dressing like a confident man.
To find out your unique body shape, take our free body shape quiz for men.
Once you know your unique body shape, take the second free quiz to discover your unique colour palette.
2. Find Your Unique Colour Palette
Remember, the garments that compose your outfits come in various colours, and you must ensure that each hue complements your natural colour.
To do that, you have to find out your seasonal colour palette, and you can do it by taking our free seasonal colour quiz for men.
3. Find Your Ideal Fashion Style
By now, you should already know your body shape and unique colour palette; the next step is to discover your ideal personal fashion style.
The fastest and simplest way is to take our free fashion style quiz for men; it includes your ideal style, outfit ideas, relevant fashion brands, and much more.
4. Professional Image Consultancy with The VOU
And if you want to style like a professional, by occasion, location, season, and time of the day, you can always ask our expert image consultants and fashion stylists for help.
Our styling services for men are the most comprehensive and detailed on the market, backed up by leading stylists who will guide you step by step in creating looks that communicate affluence, elegance, and endless accomplishments.
Remember, wearing luxury brands isn’t enough; to look stylish, confident, and successful, you must first know your body shape, colour palette, and ideal personal style, and only then style by occasion, location, season, and time of day.
Contact us today to save headaches, time, and money – it’s time to dress like a confident, successful gentleman of exquisite fashion taste –Â the first styling assessment is on us!