The enduring appeal of Ivy style clothing is its handsome simplicity. In the wrong hands this can translate to uniform dullness. In the right hands it is a smartly curated palette of classic items that can create an endless combination of outfits as timeless as they are traditional. This piece is as much a practical guide as an argument for Ivy’s unmatched casual elegance and versatility.
I expect that most people who embrace dressing in an Ivy style will be well on their journey before they realize that such a thing as a defined “Ivy Style” even exists. I grew up in Boston where the LL Bean Duck boots I borrowed from my parents were not “trad” but simply practical hand-me-downs. In Back Bay the Brooks Brothers flagship and Ralph Lauren ruled over Newbury Street, and J. Press and the Andover Shop were the most attractive and cozy menswear shops in Harvard Square. Those stores didn’t represent a subculture to me; they were simply my primary examples of what stylish men wore. Today I can recognize them as pillars of Ivy/Trad/Prep, but back then they had no mythos in my mind beyond “nice clothes.”
Which is all to say that I don’t expect anyone to create a capsule wardrobe from scratch in one go, nor would I encourage them to. Favoring one style of dress is likely a slow unintentional journey that you are well on your way towards before realizing that you began it. If you are new to this style it would be best to ease in with a few pieces before starting to obsess over the longest oxford collar points available.
In the future I will expand on this list (and many more items besides) with buying recommendations, histories, styling examples, and much more. But until then, I hope you’ll take some inspiration from this primer.
The Foundation
If you dress in an Ivy style and live someplace that has a semblance of seasonal changes, then the following wardrobe will get you through most of your days.
This list is not a buying guide, nor is it an attempt to create an Ivy fashion canon. It is a selection of items that are the backbone of my 2020s Ivy wardrobe. The individual items pictured are not necessarily the best, “the ultimate,” or the most traditional, rather they are all representative examples readily available from brands I like.
I have deliberately omitted suits, and for sanity’s sake I am not including underwear, socks, etc., nor purely practical clothing like athletic wear.
Shirts
Five or so oxford cloth button down shirts (OCBDs)
The indispensable workhorse of the Ivy wardrobe, perfect for the most casual of outfits up to odd jacket and tie. And the right suit. A tuxedo if you’re a maniac. Solid light blue and white are essential. University stripes in dusty blue and red come next. Then pink? Green? Reverse stripes? The world is your oyster pearl gray rear collar button.
Sweaters
One Shetland Sweater
There’s no reason to limit yourself to one sweater, but if I could only have one it would have to be a brushed Shetland sweater with a little white dog wagging its tongue on the label. Substantial, and available in a rainbow of colors, shetland sweaters should be your second skin in the winter.
One cotton sweater or plain crewneck sweatshirt
It’s easy to dismiss this as disposable hoody territory, but an upgraded cotton pullover should not be overlooked. Breathable and washable, cotton sweaters can be worn to the beach or the barbecue with no fear of saltwater or mustard. Like denim, they look even better broken in and faded.
Jackets
One tweed sport coat
You can’t go wrong with a nice herringbone tweed. But maybe add a subtle plaid, an overcheck, subtle flecks of orange in your murky browns and greens…Now things are getting exciting.
One navy blazer
Distinct from a navy suit jacket, an undarted, center vent, 3/2 roll navy hopsack blazer with patch pockets and gold buttons is something of the ultimate preppy jacket. I have one in my closet—and I hardly ever wear it. There’s always the risk of looking like a schoolboy, or like you’ve wandered off from the yacht club. The correct position in life (or styling) can mitigate this risk. So can swapping out the brass buttons for dark horn, but where’s the fun in that?
Pants
Two or three pairs of cotton khaki trousers
High rise, flat front, 100% cotton. The most boring item on this list. It’s very easy to do khakis wrong, or to do them adequately. However, great khakis do exist, with the same durable construction and detailed charms of an oxford shirt. I stick to earth tones, but the oxford’s color breadth is also available in trousers if one is determined to draw attention to their legs.
One pair of gray flannel trousers
Significantly increases the formality of an outfit, and I would argue, the comfort as well.
One pair of straight-leg jeans
Purists might recoil, but you need a pair of jeans. You most likely own multiple pairs. But how about a higher rise, generous legs, straight cut, lightening the wash? Tuck your shirt in.
Shoes
One pair of penny loafers
Dress them up. Dress them down. Once a good pair of loafers has molded to your feet you’ll forget that you’re even wearing them. Your most versatile color choices are dark brown or Color 8 (a dark reddish brown short of burgundy).
One pair of Suede Chukkas
These can be sleek and dressy to pair with tailoring, or rough hewn moc toes to go with jeans on the weekend. Suede shoes are very versatile and do not need to be babied (though some waterproofing spray doesn’t hurt). When in doubt, suede ankle boots will give you an edge on sneakers while remaining agreeably comfortable and casual.
One pair of white sneakers
A separate category from what you wear to the gym. Existing in a price range beneath $100, a comfortable yet handsome beater shoe to give your feet a break. Take inspiration from old school tennis, boating, or jogging with Dustin Hoffman.
Outerwear
One single-breasted mac raincoat
It’s important to have outerwear that can appropriately cover tailored clothing.But as much as I adore double breasted trench coats, they can be a bit much for daily wear unless paired with a suit and a leather briefcase. A single breasted trench coat or shorter Mackintosh rain jacket is infinitely more versatile and my primary outerwear yearound.
One Windbreaker or Anorak
Probably the broadest range of form, function and formality of any of these categories. I’m lumping Barbour jackets, windbreakers, and ponchos together in a category I would describe as thoughtfully practical. You need a water-resistant jacket with a zipper. Exactly what form it takes will depend on your climate, budget, and affection for excessive pockets.
Accessories
One striped repp tie
It’s just a striped tie. But buy the right one and you’ll have a great striped tie.
One knit tie
People who make cracks about wearing a tube sock around your neck just don’t get it.
(My dad told me that he did once wear an inner tube around his neck to meet the tie requirement of his prep school’s dress code. His teachers were not amused.)
