Ivy Style contributing writer Matthew Moskowski is a student at The Catholic University of America. Matthew is enthused with bringing prep to campus. He is studying business management and philosophy and is an active member of the campus community. Matthew serves as Vice President of the Student Body, Vice President of the Dean’s Student Advisory Council, and President Emeritus of the Business & Philosophy Club.
Matthew Moskowski
Finding myself now in my third year of university, I can safely say that I have established a style unique to myself and truly representative of my character. I firmly believe that the way a man dresses is a service both to himself and the world. It is an expression of who you are as well as how you want to be perceived. Now, from the beginning, I ought to make it clear that I do have certain prejudices against types of clothing, and that I’m not a sartorial relativist.
While many are arbitrary, according to my general immature vice of rejecting things at face-value, there are some objective standards one ought to be aware of if he wishes to take some genuine care in picking out appropriate vêtements:
1. No polyester. Ever.
The Graduate (1967) – good advice for business, bad advice for clothing
2. Try not to buy anything new. There’s plenty of waste in the world already. Plus, what has lasted until now has the survivorship bias of lasting longer in the future. Be timeless!
Ralph Lauren Vintage
3. Never wear brand logos. You’re not a billboard.
This GAP hoodie is a definite “no” – it simply advertises the brand.
4. Don’t mix metals or leathers (e.g. wear a brown belt with brown shoes and a gold watch with gold belt. The exception lies in a gold signet ring, which ought to be worn universally).
Gold signet ring from the author’s alma mater
5. Never wear black leather with anything but gray or navy fabric. You’d be surprised how often I’ve seen khaki trousers paired with black oxfords. You’re not a British soldier.
Tropic Twill Carry-On Jacket and Pant from Buck Mason. The brown shoes are the appropriate color for the khaki outfit.
6. Get a good pair of leather-soled shoes for God’s sake. Avoid at all costs the modern insult to nature that is the hybrid of ‘leather’ uppers with white rubber soles.
The Cromwell Penny Loafer in dark brown suede from Jay Butler. The shoe has a durable full leather sole that can be resoled or recrafted.
7. Have a constant mental image of the colour wheel. Don’t wear too many things of the same value or family (cool vs. warm).
These gentlemen look great in their navy blazers and Nantucket Reds. But just imagine if the blazers were the same color . . .
8. Don’t be afraid to dress casually. It took me a long time to be free in this sense (now I happily write wearing a button-down shirt with jeans, magenta socks, and penny loafers). Prep is meant to be a bit sloppy, you can get away with some stylish convenience.
Casual cool epitomized by Paul Newman
9. Limit yourself to one statement piece at a time, e.g. don’t wear a Winchester shirt with tartan trousers, or a bold pocket square with a loud tie.
Only one item of clothing here is a statement piece. The rest is about understatement.
10. Don’t be afraid of sticking to what is simple; a crisp white shirt never fails. It’s better to stick to the blandness of the menswear uniform [gray trousers, navy blazer] and be expressive with the fit and fabrics than to be chintzy and loud.
Senator Prescott Bush looking dapper in a grey three-piece suit, white shirt, and repp tie
11. That brings me into my next point: fit and fabric are everything. Get trousers that drape properly and barely break over the top of your shoe. Cuffed hem if you can manage. For brownie points (and maximal comfortability as well as height perception) find a mid-to-high rise that fits firmly around your navel. Make sure your jacket covers your ass and reaches just about the first or second knuckle of your hand when they lay by your side. Avoid shoulder pads.
J. Press tan cotton poplin suit. Three button sack model with natural shoulders. A classic Ivy League staple.
12. Prioritize a wardrobe of essentials–gray flannel trousers, a navy blazer, white and blue-stripe shirts, a navy and gray suit, simple rep ties, tan chinos–before investing in specialty items which ought to be worn less often. It’s perfectly acceptable to go out and acquire seersucker trousers or a tweed sports coat, but these things ought to come after you’ve already established yourself. Plus, they stand out and as such cannot be worn very often. Don’t be the guy who thinks he’s an academic because he always wears the same ratty tweeds.
Repp ties from The Andover Shop
13. Socks. Never white athletic socks with dress shoes. Match your socks with the colour of your trousers when wearing a suit. If dressing more casually, patterns like argyle, stripes, or even small decorative icons are acceptable, just don’t be excessively loud. Socks can be gone without when wearing boat shoes or loafers in the summer, but you should probably always wear socks when you’re wearing trousers.
Argyle socks
I have no doubt that I am missing plenty in attempting to give this brief overview of the standards by which I dress. Frankly, my current expression of style is due to change in some ways over the course of my life. I’d advise that, as I did, you look to some role models. For more traditional tailoring and suits I always prefer the looks of Cary Grant
or Gregory Peck.
Cary Grant in publicity shot for the Alfred Hitchcock thriller North by Northwest (1959)Gregory Peck in To Kill a Mockingbird (1962)
When accessing the casual but refined look emanating from my New England sensibilities, it’s always JFK. Humbly I remind myself often that this is not something I was raised with, but chose for myself. I don’t come from money (or particularly good taste…), but nevertheless I’ve found my way.
President John F. Kennedy
What’s most important with choosing your own style is that it’s genuine. Be true to yourself and never deceive the world by trying to fit in. I’ve never much respected those who make such an exhausting effort to avoid standing out. On the other hand, there are those so excessively and obviously boastful of their adequate sartorial knowledge that they brag by the very fact of walking into the room with some second-hand cordovan or distressed denim. For one, you ought never to feel nor appear as if you’re wearing a costume. What’s more, you ought to be subtly expressive, such that the clothes are a mere gateway to your far more interesting self.
Matthew Moskowski
I hope that with this summary I have provided some helpful direction. When in doubt, play it safe and simply ask what the Royals would do (King Charles a supreme example himself of balancing esteem and ease). When people notice your wonderful taste in tailoring or footwear, simply give a polite nod and ‘thank you’ without drawing attention to your sources or bragging about how rare a find such and such article was.
The British Royal Family
Many will be sure to admire your style, even if they cannot name the exact thing that ties it together. If there’s anything to remember most of all, it’s that you ought to be real. Costumery and bullshit are very easily detectable, and edifying for neither party. Best of luck to you in your various endeavours as you enter into this exciting world of great taste. I’m glad I could be a source of interest, and maybe a little bit of help.
Yes, this is a fine primer. My only quibbles are that this is really about Ivy or collegiate as it existed before Love Story, not prep, certainly not prep as (if?) it exists today; repp has two Ps; and, although we know what chinos are, I prefer to call them khakis. These are all excellent observations, but I send up special thanks for the inclusion of casual with the bottle of Heineken and the comment regarding a bit of sloppiness. The pictures selected are terrific.
Tim, agreed that this is about classic collegiate style which predates Love Story. Matthew’s excellent summary would have been considered good sartorial advice circa 1950. Despite the modern concept of “prep” – which seems to be based on the idea that anything goes – The Official Preppy Handbook (1980) provides detailed descriptions of men’s clothing which match up rather perfectly with what we call Ivy. Side note: my grandfather, Harvard MBA who lived in Westport back in the days when Paul Newman was also a resident, always had Heineken on his sailboat. He resembled Newman in this photo much more than, say, Thurston Howell III.
I really do not have a recollection of “statement pieces” in the early fifties, but in the mid-fifties, I recall the fad of charcoal and pink. In the late fifties the world seemed to think red socks were a good idea. The earliest statement pieces I recall would be in the mid-sixties when muted Madras was overtaken by brighter colors and tartan pants and vests crept into holiday wardrobes, mercifully one or the other. Following up on my earlier reference to khakis, the only chinos I recall were polished cotton, and they never caught on with my classmates.
“Prep” at a *Catholic* institution? There was a time when that was considered a contradiction in terms. No more, of course, and that’s as it should be.
But let’s just insert a historical parenthesis here and remember that, aside from the Kennedys and the Buckleys and a few other families whose extreme wealth managed to provide them with at least partial, with-an-asterisk access to the world of “prep,” that world was pretty much closed off to Roman Catholics.
As far as religious affiliation was considered, the choices were Episcopalianism or Episcopalianism, full stop.
Yes indeed! I have earned degrees at five colleges. My undergraduate institution, Trinity College, was founded by Episcopalians. I hold master’s degrees from Harvard and Yale, both founded by Puritans whose descendants often joined the Episcopal Church. I also attended two Catholic institutions, Fairfield University (Jesuit) and Salve Regina University (Sisters of Mercy). On Thursday I will attend the graduate commencement ceremony at Salve for my Ph.D. program. My doctoral dissertation “Dreaming Spires” focuses on the impact of Episcopalians on Collegiate Gothic architecture.
Looking sharp in your two photographs, Matthew! Please come speak to the male students, staff, and faculty at my Upper Midwestern institution. We need your guidance. Desperately.
And hear, hear to #6! Those pedal abominations kill me! Is it a shoe? Is it a sneaker? They’re the best way to ruin a good ensemble. They look like something Del Boy would flog down the market along with cat figurines that sing “how much is that doggie in the window”.
I could not agree more, M_K. Brown leather uppers with white rubber soles look ridiculous, and yet I see them everywhere, sometimes even worn with a coat and tie. I make an exception for Topsiders and other boat shoes, of course, which are an entirely different matter.
Mr. Moskowski – Excellent advice all around. Please continue to set a great example.
He’s basically mastered Ivy Style. Whilst it is a personal style, I wouldn’t call this a 100% authentic style, and I think the author would agree. But it’s a damn good execution of Ivy style, he’s basically perfected all of the basics and has good grooming. There’s still room to really personalise things and work more on the minutia but it’s basically done. Well done sir, your making the world a more stylish place!
Actually, I think my dad wore black shoes with his tan summer uniform. It had a short sleeve, open collar (almost like a camp collar) shirt with identical colored pants. It was crucial for the San Antonio heat.
You look well put together. My only suggestion is a smaller pair of eye glass frames. The pair you are wearing are too large for your face. Look for a frame size of less than 50mm.
Good job, Matthew. To single out just one bit of good advice, “Avoid at all costs the modern insult to nature that is the hybrid of ‘leather’ uppers with white rubber soles.” Absolutely! Where did this hideous fad come from? I see it everywhere.
Several excellent points listed here. Point #2 is one I have firmly believed in for years. Used quality, timeless articles of clothing are not only a great value, but they each have a story to tell.
Mr. Moskowski: Congratulations on this article. I will go ahead and apologize for my lengthy reply, but I have a few comments.
Firstly, I am always encouraged when a young man chooses to preserve the traditions and vetements of the Ivy League, and its first cousin, the southern collegiate style. And as you imply, the vetements should include not only clothing, but accoutrements as well, the total package: belts, socks, wristwatches, eyewear, ties, pocket squares, rain gear and umbrella, and for the women, the handbag, scarves, jewelry, etc.
Secondly, I draw a distinction between the Ivy League style of the late 1950’s/60’s and its later iteration, the Preppy style, which came along in the late 1970’s/80’s. In my opinion, the Preppy phenomenon is a spin-off or sequel to old Ivy. As they say in the merchandising and marketing department, Preppy is a totally different customer.
Here are some comments on your numbered points.
1. No polyester. Ever. – Sound advice! Having said that, I admit that I have occasionally worn trousers made of a wool and Dacron blend. But I am one of the few men my age who can honestly say that he never owned a garment made of polyester double knit or wore bell-bottom trousers or owned a pair of white patent leather loafers or boots.
2. Try not to buy anything new. – Easier said than done! Not all of us are a perfect 40-Long. I cannot even walk into a fine clothier today (except for perhaps O’Connell’s) and find a three button, natural shoulder, center hook vent, non-darted suit, navy blazer or Tweed sport coat in a 46-Extra Long – much less find one in a thrift store.
3. Never wear brand logos. – Good for you! I also refuse to be a walking, talking advertisement for a clothing manufacturer or retailer.
4. Don’t mix metals or leathers. – Wholeheartedly agree!
5. Never wear black leather with anything but gray or navy fabric. – Sound advice!
6. Get a good pair of leather-soled shoes. – Only one pair? Caveat on the shoes with white rubber soles. Allbirds (mesh uppers with white soles) are comfortable and look great with khakis or blue jeans, an OCBD and off-white socks. But not with coats and ties, please!
7. Have a constant mental image of the color wheel. OK, no problem, but after a while the appropriate selection of complementary colors just becomes automatic or second nature.
8. Don’t be afraid to dress casually. Sound advice! But really? Magenta socks? Sorry, you lost me there.
9. Limit yourself to one statement piece at a time. – Sound advice!
10. Don’t be afraid of sticking to what is simple. No problem with that!
11. Fit and Fabric are everything. I question your assertion that trousers should “barely break over the top of your shoe.” My view is –- and this is based on the advice of a number of Ivy aficionados -– that there should be NO BREAK at the top of the shoe and the trousers should always have 1¾” cuffs. And as you may or may not know, long rise trousers are few and far between these days. Clothing manufacturers seem to have jumped on the “one size fits all” bandwagon.
12. Prioritize a wardrobe of essentials – gray flannel trousers, a navy blaze, etc. – I agree.
13. Socks: never white athletic socks with dress shoes. – You are absolutely correct. However, there is one nuanced permutation which occurs when you throw a pair of Wigwam off-white 100% wool socks in the washing machine with a little Clorox. The socks turn a beautiful shade of golden/beige. When these are worn with Weejuns® and khakis, it is a great “look” from the early 1960’s. I agree entirely that “no socks” with boat shoes or loafers” are OK, but never with lace-up shoes. That makes no sense whatsoever!
By the way, you mention King Charles III and his sartorial splendor. Honestly, even I would look good in a £5000 bespoke suit from Savile Row and a £400 shirt from Turnbull & Asser.
Mr. Moskowski, I am considerably older than you. (I was wearing Weejuns®, khaki pants, an OCBD’s with a regimental striped tie and a navy blazer sixty years before you grew out of your first Winnie-the-Pooh onesie.) Even still, I agree wholeheartedly with almost all your points. I hope to hear more from you on Ivy Style going forward. – James H. Grant
loved #9 with Paul Newman. Nothing better then to wear on those Summer mornings is a old frayed collared OCBD in light blue unbuttoned all the way and sleeves rolled up, with navy t shirt under it ,a pair of Nantucket red shorts and sperry top siders
Excellent summary, Matthew! Keep up the good work.
Yes, this is a fine primer. My only quibbles are that this is really about Ivy or collegiate as it existed before Love Story, not prep, certainly not prep as (if?) it exists today; repp has two Ps; and, although we know what chinos are, I prefer to call them khakis. These are all excellent observations, but I send up special thanks for the inclusion of casual with the bottle of Heineken and the comment regarding a bit of sloppiness. The pictures selected are terrific.
Tim, agreed that this is about classic collegiate style which predates Love Story. Matthew’s excellent summary would have been considered good sartorial advice circa 1950. Despite the modern concept of “prep” – which seems to be based on the idea that anything goes – The Official Preppy Handbook (1980) provides detailed descriptions of men’s clothing which match up rather perfectly with what we call Ivy. Side note: my grandfather, Harvard MBA who lived in Westport back in the days when Paul Newman was also a resident, always had Heineken on his sailboat. He resembled Newman in this photo much more than, say, Thurston Howell III.
I really do not have a recollection of “statement pieces” in the early fifties, but in the mid-fifties, I recall the fad of charcoal and pink. In the late fifties the world seemed to think red socks were a good idea. The earliest statement pieces I recall would be in the mid-sixties when muted Madras was overtaken by brighter colors and tartan pants and vests crept into holiday wardrobes, mercifully one or the other. Following up on my earlier reference to khakis, the only chinos I recall were polished cotton, and they never caught on with my classmates.
“Prep” at a *Catholic* institution? There was a time when that was considered a contradiction in terms. No more, of course, and that’s as it should be.
But let’s just insert a historical parenthesis here and remember that, aside from the Kennedys and the Buckleys and a few other families whose extreme wealth managed to provide them with at least partial, with-an-asterisk access to the world of “prep,” that world was pretty much closed off to Roman Catholics.
As far as religious affiliation was considered, the choices were Episcopalianism or Episcopalianism, full stop.
Yes indeed! I have earned degrees at five colleges. My undergraduate institution, Trinity College, was founded by Episcopalians. I hold master’s degrees from Harvard and Yale, both founded by Puritans whose descendants often joined the Episcopal Church. I also attended two Catholic institutions, Fairfield University (Jesuit) and Salve Regina University (Sisters of Mercy). On Thursday I will attend the graduate commencement ceremony at Salve for my Ph.D. program. My doctoral dissertation “Dreaming Spires” focuses on the impact of Episcopalians on Collegiate Gothic architecture.
https://digitalcommons.salve.edu/doctoral_dissertations/236/
Looking sharp in your two photographs, Matthew! Please come speak to the male students, staff, and faculty at my Upper Midwestern institution. We need your guidance. Desperately.
Kind Saturday Regards,
Heinz-Ulrich
Some nice bits of style advice, young Matthew. May your peers be inspired by your example.
Pax vobis!
And hear, hear to #6! Those pedal abominations kill me! Is it a shoe? Is it a sneaker? They’re the best way to ruin a good ensemble. They look like something Del Boy would flog down the market along with cat figurines that sing “how much is that doggie in the window”.
I could not agree more, M_K. Brown leather uppers with white rubber soles look ridiculous, and yet I see them everywhere, sometimes even worn with a coat and tie. I make an exception for Topsiders and other boat shoes, of course, which are an entirely different matter.
Mr. Moskowski – Excellent advice all around. Please continue to set a great example.
Good point number 4, on metals and leathers.
He’s basically mastered Ivy Style. Whilst it is a personal style, I wouldn’t call this a 100% authentic style, and I think the author would agree. But it’s a damn good execution of Ivy style, he’s basically perfected all of the basics and has good grooming. There’s still room to really personalise things and work more on the minutia but it’s basically done. Well done sir, your making the world a more stylish place!
One US Navy uniform pairs khaki with black shoes.
That’s the Navy for ya, says the Air Force brat.
In the fifties brown shoes were often allowed.
Actually, I think my dad wore black shoes with his tan summer uniform. It had a short sleeve, open collar (almost like a camp collar) shirt with identical colored pants. It was crucial for the San Antonio heat.
I’ve always thought that black oxfords were the best shoes with a Glen Plaid suit.
You look well put together. My only suggestion is a smaller pair of eye glass frames. The pair you are wearing are too large for your face. Look for a frame size of less than 50mm.
Good job, Matthew. To single out just one bit of good advice, “Avoid at all costs the modern insult to nature that is the hybrid of ‘leather’ uppers with white rubber soles.” Absolutely! Where did this hideous fad come from? I see it everywhere.
Please continue to set a great example.
Several excellent points listed here. Point #2 is one I have firmly believed in for years. Used quality, timeless articles of clothing are not only a great value, but they each have a story to tell.
The Army Air Corpse or Army Air Force changed the shoes from tan to black when they became the US Air Force in around 1949.
Mr. Moskowski: Congratulations on this article. I will go ahead and apologize for my lengthy reply, but I have a few comments.
Firstly, I am always encouraged when a young man chooses to preserve the traditions and vetements of the Ivy League, and its first cousin, the southern collegiate style. And as you imply, the vetements should include not only clothing, but accoutrements as well, the total package: belts, socks, wristwatches, eyewear, ties, pocket squares, rain gear and umbrella, and for the women, the handbag, scarves, jewelry, etc.
Secondly, I draw a distinction between the Ivy League style of the late 1950’s/60’s and its later iteration, the Preppy style, which came along in the late 1970’s/80’s. In my opinion, the Preppy phenomenon is a spin-off or sequel to old Ivy. As they say in the merchandising and marketing department, Preppy is a totally different customer.
Here are some comments on your numbered points.
1. No polyester. Ever. – Sound advice! Having said that, I admit that I have occasionally worn trousers made of a wool and Dacron blend. But I am one of the few men my age who can honestly say that he never owned a garment made of polyester double knit or wore bell-bottom trousers or owned a pair of white patent leather loafers or boots.
2. Try not to buy anything new. – Easier said than done! Not all of us are a perfect 40-Long. I cannot even walk into a fine clothier today (except for perhaps O’Connell’s) and find a three button, natural shoulder, center hook vent, non-darted suit, navy blazer or Tweed sport coat in a 46-Extra Long – much less find one in a thrift store.
3. Never wear brand logos. – Good for you! I also refuse to be a walking, talking advertisement for a clothing manufacturer or retailer.
4. Don’t mix metals or leathers. – Wholeheartedly agree!
5. Never wear black leather with anything but gray or navy fabric. – Sound advice!
6. Get a good pair of leather-soled shoes. – Only one pair? Caveat on the shoes with white rubber soles. Allbirds (mesh uppers with white soles) are comfortable and look great with khakis or blue jeans, an OCBD and off-white socks. But not with coats and ties, please!
7. Have a constant mental image of the color wheel. OK, no problem, but after a while the appropriate selection of complementary colors just becomes automatic or second nature.
8. Don’t be afraid to dress casually. Sound advice! But really? Magenta socks? Sorry, you lost me there.
9. Limit yourself to one statement piece at a time. – Sound advice!
10. Don’t be afraid of sticking to what is simple. No problem with that!
11. Fit and Fabric are everything. I question your assertion that trousers should “barely break over the top of your shoe.” My view is –- and this is based on the advice of a number of Ivy aficionados -– that there should be NO BREAK at the top of the shoe and the trousers should always have 1¾” cuffs. And as you may or may not know, long rise trousers are few and far between these days. Clothing manufacturers seem to have jumped on the “one size fits all” bandwagon.
12. Prioritize a wardrobe of essentials – gray flannel trousers, a navy blaze, etc. – I agree.
13. Socks: never white athletic socks with dress shoes. – You are absolutely correct. However, there is one nuanced permutation which occurs when you throw a pair of Wigwam off-white 100% wool socks in the washing machine with a little Clorox. The socks turn a beautiful shade of golden/beige. When these are worn with Weejuns® and khakis, it is a great “look” from the early 1960’s. I agree entirely that “no socks” with boat shoes or loafers” are OK, but never with lace-up shoes. That makes no sense whatsoever!
By the way, you mention King Charles III and his sartorial splendor. Honestly, even I would look good in a £5000 bespoke suit from Savile Row and a £400 shirt from Turnbull & Asser.
Mr. Moskowski, I am considerably older than you. (I was wearing Weejuns®, khaki pants, an OCBD’s with a regimental striped tie and a navy blazer sixty years before you grew out of your first Winnie-the-Pooh onesie.) Even still, I agree wholeheartedly with almost all your points. I hope to hear more from you on Ivy Style going forward. – James H. Grant
loved #9 with Paul Newman. Nothing better then to wear on those Summer mornings is a old frayed collared OCBD in light blue unbuttoned all the way and sleeves rolled up, with navy t shirt under it ,a pair of Nantucket red shorts and sperry top siders