Head to Toe: Casual Ivy
Crafting Casual Ivy: A Deep Dive into Starter Wardrobe Staples
On the last episode of my podcast, I received the question: 'Can you cover a head-to-toe/starter staples wardrobe for a casual/relaxed Ivy style?'
I really liked this question but wanted to revisit it and explore it in more depth.
There are lots of guides out there, and if you’re reading this, you’re probably already somewhat acquainted with how to dress in Ivy style. To be honest, it’s not really my thing to dictate how you should be doing it. Rather than setting rules for you to follow, this is more of a guide to some of the pieces I’d recommend.
Obviously, it’s up to you how you dress. How formal you want to be is entirely your choice. However, for many, a more casual option may be more suited to their lifestyle.
So, here you go: my personal take on some labels I’d recommend for crafting an everyday casual Ivy wardrobe.
1. Caps
Ebbets Field Flannels
Ebbets Field Flannels started back in 1988 when founder Jerry Cohen set out to recreate authentic, vintage baseball jerseys and caps from forgotten teams and leagues, like the Negro Leagues and the Pacific Coast League. The name comes from Brooklyn’s iconic Ebbets Field, home of the Dodgers until 1957, and reflects the brand’s dedication to capturing the spirit of baseball’s golden era. What began as a small passion project has grown into a beloved brand for anyone who appreciates the history and style of old-school sportswear.
I bought an Ebbets hat second-hand from Vinted for a fraction of the price they usually go for. They’ve got loads of brilliant designs, but this one has always caught my eye, so when it popped up, I had to get it. It’s for the New York Black Yankees.
Smathers and Branson
Smathers & Branson was founded in 2004 by two college friends, Peter Smathers Carter and Austin Branson, who saw an opportunity to bring classic needlepoint craftsmanship into modern accessories. The brand started with handmade belts and quickly expanded to include a range of products, from wallets to key fobs, all featuring their signature needlepoint designs.
The one below here is one with the Princeton college shield. Again, this one was bought second hand. All Blues Co did stock these a few years ago, but not at the moment. I’d love to see these return to UK shelves again!
Smathers and Branson also produce hats for J. Press by incorporating their signature hand-stitched designs into classic cap styles.
These are good enough a reason for me to return to New York and pick one up.
2. Shirts: Oxford Cloth Button-Downs (OCBDs)
Kamakura Shirts
Now, we all know the obvious ones—Brooks Brothers, I’m looking at you! But it’s brands like Kamakura Shirts that bring something extra to the table, blending Japanese craftsmanship with timeless, Ivy-inspired style.
Kamakura Shirts was founded in 1993 by Yoshio Sadasue and his wife Tamiko in Kamakura, Japan. With a commitment to creating high-quality dress shirts at an affordable price, the brand quickly became known for its blend of traditional Japanese craftsmanship and Ivy League-inspired style. Yoshio Sadasue's experience with VAN Jacket, the iconic Japanese brand that introduced Ivy style to Japan in the 1960s, played a key role in shaping Kamakura's aesthetic.
There are plenty of differing opinions on Kamakura shirts online, but I find they fit me particularly well. It just seems to work for me. Not every brand is going to be right for everyone, but Kamakura certainly does the job for me.
Pictured below are the ones I have in my collection, including a corduroy option (bending the rules of an OCBD, I know!).
3. Rugby shirts
Barbarian Rugby Shirts.
Barbarian Rugby Shirts started in Canada back in 1981 and quickly gained a reputation for their tough, heavyweight cotton construction. They’re the kind of shirts that look great on or off the field, combining classic rugby style with a bit of casual flair.
You either love or hate rugby shirts—I definitely fall into the love camp! I’ve mentioned it before, but they’re such a versatile piece, sitting somewhere between a sweatshirt and a long-sleeve T-shirt. I’d say they’re the perfect garment for autumn, providing just the right amount of warmth while still looking effortlessly stylish.
I have to also be loyal to one of my favourite brands out there—Trickett England. They made this one pictured below in Wimbledon colours to coincide with the 2024 games.
4. Layering: Sweatshirts
I’ll be showcasing two options here: a high-end sweatshirt from Eastman that highlights premium craftsmanship and a more budget-friendly choice from Uniqlo that delivers style and comfort.
Eastman Leather Clothing has been around since 1984, focusing on vintage-style flying jackets and accessories that aim for true authenticity. Their pieces are inspired by classic designs, originally made for function and protection in tough conditions. What sets Eastman apart is their commitment to detail—each jacket is crafted in the UK by skilled artisans who take pride in their work.
This sweatshirt is crafted using classic mid-20th century techniques and machinery, resulting in a fabric that’s truly top-notch. You can feel the premium quality as soon as you touch it, and the comfort is outstanding when worn.
Featuring a high waistband and cuffs that enhance both style and fit. Yes, it’s a navy sweatshirt, but it’s not just any navy sweatshirt.
Uniqlo, a more affordable option that definitely deserves your attention. Known for their stylish and functional basics, Uniqlo offers sweatshirts that combine comfort with great design. With a variety of colour options available, you can easily find the perfect piece to fit your personal style without breaking the bank. Whether you’re looking for something classic or a bit more vibrant, Uniqlo has you covered
5. Cold-Weather Option: Shaggy Dog Sweaters
Harley Of Scotland
Next up is Harley of Scotland and their classic Shaggy Dog jumpers. You can often picture Ivy Leaguers on the East Coast wearing their Shaggy Dog jumpers, especially during those cool autumn days. There’s a certain classic style to them that fits right in with the collegiate look.
Mine comes out the wardrobe as soon as the temperature drops. It’s like Christmas day.
6. Trousers: Chinos
Buzz Rickson's was founded in Japan in the early 1990s, inspired by vintage American military clothing. The name comes from a character played by Steve McQueen in The War Lover, adding a touch of cinematic history. Known for its authentic reproductions using original fabrics and techniques, Buzz Rickson's has earned a dedicated following among military apparel enthusiasts who appreciate quality and attention to detail.
These are based on the 41 U.S. Military standard issue, they feature a modified fit that offers a more tailored look while still being comfortable to wear. Made from durable 100% cotton chino cloth, they boast strong twin needle stitching and handmade pockets.
7. Socks: College Socks
Ivy Ellis
Ivy Ellis Socks started during the Covid lockdown of 2020, when the founders found themselves with extra time and a passion for vintage sportswear and the Ivy League style. What began as a few sketches at the kitchen table turned into a creative project that quickly grew beyond their initial vision. Balancing busy lives, they transformed their love for classic designs into a brand that celebrates that timeless Ivy aesthetic.
I’m a huge fan of Ivy Ellis; in fact, they fill the majority of my sock drawer!
8. Footwear: Penny Loafers
GH Bass was founded in 1876 by George Henry Bass in Wilton, Maine. The brand gained fame in the 1930s with the Weejun loafer, which combined comfort and classic style. I’ve been wearing GH Bass for years and appreciate how their designs have stood the test of time.
As well as Ivy Leaguers, jazz musicians also favoured the Weejun for its sleek look, further cementing its place in the culture of the time. The combination of these influences made GH Bass a go-to choice for students and artists alike, symbolising a laid-back yet sophisticated approach to style.
Redefining Ivy style doesn’t mean reinventing the wheel; it’s about adding personal flair and modern twists to classic staples. By understanding the history, exploring contemporary trends, and applying your own style, you can create outfits that are both timeless and uniquely yours. Embrace these essentials with a fresh perspective and let your wardrobe tell your story.
What are some of your favourite labels?
Thanks for reading,
Tom
Great post Tom! A number of brands here I need to check out. That Trickett rugby is 👌One of my favourite labels is Oliver Spencer; a modern spin on the classics with quality fabrics.