Buying into Preppy/Ivy League Trad

Greetings, I am a 37 y/o minimalist social worker in Los Angeles, CA with a pretty open budget. Everything I own works together so most of my mornings are very straight forward and linear. I recently realized that Ivy NE Nantucket has one of the most versatile systems and have taken a strong liking for its ability to fit in most occasions. With that being said, many of the business casual basics brands haven’t held up over the years and am interested in what you might recommend. I am looking at: PRL, Brooks Brothers, JPress, LL Bean, Land's End, Pradagonia, Charles Tyrwhitt, Vineyard Vines, Crockett and Jones, etc. I'm just left thinking, “What would JFK do?”. Looking to start a wardrobe basically from scratch, from OCBDs to shoes, although I already have acquired some of the items. What would you recommend for a working professional needing basics and staples? Anything I’m missing or can remove? Thanks for your input and God Bless America! 1. Shirts 1. White Oxford Cloth Button-Down (OCBD) - Brooks Brothers 2. Light Blue OCBD - Brooks Brothers 3. Long-Sleeve Henley - J Crew 4. Black Shirt x 2 5. White shirt x 3 2. Sweaters 1. Mid-Grey Crewneck Sweater – LL Bean 2. Navy Shetland or Lambswool Crewneck – LL Bean 3. Trousers 1. Khaki Chinos – Lands End/BB 2. Stone Chinos - Lands End/BB 3. Grey Flannel Trousers – autumn/winter smart essential. ? 4. Dark Raw Denim – casual base. Levis 4. Jackets 1. Navy Blazer (Soft-Shouldered) – hopsack, worsted wool for year-round wear. 2. Sports Coat - Caruso 3. Tweed Sport Coat – brown/grey herringbone, fall/winter anchor. ? 4. Beige Harrington Jacket - Ben Sherman 5. Full Black Suite - Caruso or Bespoke Tailor 5. Outerwear 1. Waxed Cotton Jacket - Barbour 2. Dark Navy Top/Overcoat - Vintage Brioni, whatever on eBay 6. Footwear 1. Black Dress Shoes - ? 2. Cordovan Penny Loafers – works with all pants, year-round. Crockett and Jones, Alden 3. Dark Brown Oxford dress shoes - AE, 4. White Sneakers - Oliver Cabell
15 Replies
Clark'sDesertBot
Hi @Mr Khan I Presume! For better answers, include: - Reference pictures - Budget in numbers - Specific measurements - Openness to buying secondhand and/or online - Location: country/continent is fine - Timing/urgency
Holfram
Holfram2mo ago
Alright. Personally I don’t think it’s great to think of fashion or style as a checklist, but you do you. I also think Ivy is much more multifaceted than this. I’d recommend you check out the book “Take Ivy” - it even has a checklist in the back, if you’re into that. Anyways, going over the list a few things stand out: -what is a long sleeve Polo Henley? A rugby? -Black Shirts are not usually part of an “Ivy” wardrobe -White shirts are the exception rather than the rule most of the time - oxfords in different colors are usually preferred (pink, green, yellow) -get your OCBDs from J. Press, they’re big, they’re made in the US, they have the flap pocket -get your shaggy dog shetlands from J.Press - good place to add pops of color (yellow, red etc.) -lands end is a good place to get chinos from what I heard - your grey flannel trousers are ideally the second pair of trousers that come with your grey flannel suit that you will get instead of a black one, possibly also from J.Press or O’Connels -Levi’s is not a great place to get raw denim, you could maybe try one of the copious Japanese Brands -sports coat? What kind of sports coat? Whatever it is you’ll be able to get it second hand on eBay along with your navy blazer and your tweed sports coat. -Harrington jackets are Baracuta - the older, wider fit (waistband and jacket have a different shade in this one) -get a Gloverall Dufflecoat instead of an overcoat -black dress shoes could possibly come from Allen Edmonds -rethink cordovan if you’re looking for something summery, it’s incredibly dense -your brown dress shoes might as well be derbies, you don’t need 2 pairs of oxfords probably -just get your white sneakers from sperry What’s “missing”: -where are the shorts? -where are your boat shoes/camp mocs/ranger mocs? -where are your fun options? -where are the more casual options, such as sweatshirts or T-shirts? I’d like to end with some general, non list based advice. A list does not a good wardrobe make, I’ve been there. You’ll need to build something coherent, both in look and in fit that doesn’t necessarily fit into a specific style, but something that’s authentic for you. Wear your clothes, be comfortable in them, don’t let your clothes wear you. That is what gives, specifically Ivy style, its appeal. Look at inspo pictures, get familiar with silhouettes, how tops, bottoms and shoes play together in the style that you want to try out. And don’t buy everything at once. Who knows if you’ll like it. And fwiw many of the brands that do good Ivy Staples these days will be Japanese. Though tbh the best route is to just scour eBay for some of the old stuff. Don’t think “What would JFK do?” (The answer is likely “have an affair”), think “What would I do?”. Not to toot my own horn here, but I post an inspo album every week and most of it is pretty Ivy, so you can just search the inspiration folder for that. Then check out fits by @artvandelayimporting , @zeometer ૮₍ 𝁽ܫ𝁽 ₎ა, @Dexter , @LeisurelyLoafing @Shrimp my Ride and others that I forget.
Holfram
Holfram2mo ago
Lastly here’s the Checklist from Take Ivy if you want to stick to a list:
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Holfram
Holfram2mo ago
And some guidelines from the satirical official preppy handbook from the 80s that kind of turned into a somewhat iconic guide
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Holfram
Holfram2mo ago
You’ll likely notice that much of this isn’t for you. And that’s a good thing. Dress Ivy-ish, by all means. But don’t think of dressing as something that works by going off a list, unless you plan on getting 12 ties and wearing them too. Oh and also please be aware that dressing a certain way might come with certain negative associations that I can’t speak to, because I’m not American. ✌🏻
Mr Khan I Presume
Mr Khan I PresumeOP2mo ago
I greatly appreciate your time and thoughtfulness. I find it invaluable to receive advice on more formal attire, although it is quite late in the United States, so I will thoroughly review this tomorrow. As a minimalist, it be very difficult to have a work uniform that doesn’t dominate the weekend wear so developing a style that works for both is my goal. Attached below is my whole wardrobe, so streamlining everything means the world to me. Thanks again!
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Holfram
Holfram2mo ago
So fwiw Ivy is not minimal at all. Ivy loves lots of stuff, and many Ivy wardrobes are seriously big!
Mr Khan I Presume
Mr Khan I PresumeOP2mo ago
Just inspired, that’s all:) I am looking forward to the official preppy handbook and thank you for the screen grabs!
Holfram
Holfram2mo ago
There’s a pdf of it floating around that you can get with a bit of googling
Mr Khan I Presume
Mr Khan I PresumeOP2mo ago
Ty!
grandpacore
grandpacore2mo ago
Oh hey is that a timex easy reader. I love that watch
zeometer
zeometer2mo ago
holfram had an excellent list of suggestions and cautions but i'll ask, which is more of a priority to you: - finding a minimal or optimized number of clothes - adhering to the aesthetic principles of ivy or preppy style the text suggests it might be the former and as holfram said, ivy doesn't lend itself to minimalism since people are dressing for four seasons amongst other things if you have aesthetic inclinations towards it, great! i think seeing some of the ways in which people/brands combine items may be inspiring if it's simply versatility then honestly i'd take a closer look at your specific needs. how often you do laundry, what kind of work environment (specifically), what kind of occasions do you dress for? - but also what you like visually.
LeisurelyLoafing
Needs some refreshing but should be a decent jumping off point
du☆
du☆5w ago
seeing as you are based in LA I would pause and consider what parts of the wardrobe could be applicable to you even purely from weather alone. NE is a completely different beast especially when it snows in particular the fall and spring seem brief, so the ivy wardrobe recs won’t necessarily be focused on that, while LA winter may as well be fall in NE

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