Gentlemen, we have to confront the elephant in the room which is that our preferred mode of dressing is increasingly anachronistic in a world of sweatpants, hoodies, and crocs. Perhaps if we are retired and our biological age is close to how long it's been since the heyday of the Ivy League Look, this is less of a concern. But for younger working age folks we face both situations where we'd like to stand out and where we'd like to blend in. Without capitulating to athleisure or skin-tight Italian caricatures, I think these are some concessions we can make that allow us to wear our favorite "trad" items as much as possible, while not standing out too much or be considered over-dressed by the hoi polloi.
The idea of "high/low" (which I read about from Simon Crompton) is purposely mixing items of different formalities. Presumably the original intent is to evince a certain cool/aristocratic nonchalance. But used differently, this can confuse the sartorially uninitiated and minimize getting asked "Dressed up for an interview?" when all we got is a striped oxford shirt and tucked in khakis. I find we can still preserve the Ivy uniform, if we substitute one piece for a decidedly working class (workwear) or athletic garment.
Jeans: As much rise as possible, and legs should be straight or fuller. Better if selvedge, as it is just a scooch more tasteful. With this you can wear with the dressiest shirt, sweater, overcoat, and even sport coat. You'd still be considered well-dressed in this day and age, but a bit more "normal". The tricky thing is so many shirts, sweaters, and blazers come in shades of blue or green, which IMO doesn't offer enough contrast with the pants. But on the other hand this allows for red, yellow, beige, pink tops to be worn with more frequency.
Patagonia fleece vest: Let's face it. Just a shirt tucked into proper slacks, or with a saddle-shouldered sweaters is considered old-fashioned and stuffy in 2022. A zip vest kills that sense by more than a half. If it allows me to look more normal taking out the trash or getting the mail, then Midtown Banker overtones be damned.
Rugby shirt: Good overall, but let's face it, not seen too often these days, and can be considered "weird" by the masses.
Western shirt: Theoretically a good choice to dress down an otherwise formal(er) outfit, but I don't own one at the moment. So can't speak from lived experience.
Zipper coats: Baracutas, Barbours, Filsons: I'll take them over Canada Goose and North Face any day. Also the Vietnam army field jacket (M-67?) when worn with otherwise formal ensemble (I think this is one of Simon Crompton's original examples) Truth be told they are getting rarer by the day, but they are the best I can come up with.
Ball cap (3 seasons) or beanie (winter): Not only casual and common, but handy if you can't be bothered to apply hair product during these WFH times.
Hawaiian shirts: I like popovers with button down collars, but this option seems to be summer-specific. Ditto tennis shirts and shorts.
Footwear: This is tricky if we wish to be traditional all the time (I say no running shoes unless actually running). I think suede is generally better than shiny (because if you have say calfskin you brush often and polish periodically right? that gives luster that sadly sticks out in 2022). I'm partial to dirty bucks (can look like white/beige tennis shoes from a distance), low-contrast saddle shoes entirely in suede or nubuck (easier maintenance is a plus too). Blue suede comes in handy with darker trousers. Not to leave out boat shoes, Bean blucher mocs, loafers and the ilk. Wear LL Bean hunting shoes whenever it's wet enough (they are comfy too with thick socks). Perhaps the Red Wing Moc Toe boot is also a good idea? But I doubt it, and I'm not interested in adding it to my collection.
To be honest it's hard not to stand out when others are wearing Nikes, crocs, flip flops, and lumberjack boots. But I think my choices above beat cordovan longwings and captoes, and hopefully people don't look down as often.
So these are just some thoughts in no particular order about strategies to ensure we can still wear heydey Ivy League clothes as often as we can, and not look too outlandish when "out and about" in public in 2022. Feel free to engage, flame, or glorify
The idea of "high/low" (which I read about from Simon Crompton) is purposely mixing items of different formalities. Presumably the original intent is to evince a certain cool/aristocratic nonchalance. But used differently, this can confuse the sartorially uninitiated and minimize getting asked "Dressed up for an interview?" when all we got is a striped oxford shirt and tucked in khakis. I find we can still preserve the Ivy uniform, if we substitute one piece for a decidedly working class (workwear) or athletic garment.
Jeans: As much rise as possible, and legs should be straight or fuller. Better if selvedge, as it is just a scooch more tasteful. With this you can wear with the dressiest shirt, sweater, overcoat, and even sport coat. You'd still be considered well-dressed in this day and age, but a bit more "normal". The tricky thing is so many shirts, sweaters, and blazers come in shades of blue or green, which IMO doesn't offer enough contrast with the pants. But on the other hand this allows for red, yellow, beige, pink tops to be worn with more frequency.
Patagonia fleece vest: Let's face it. Just a shirt tucked into proper slacks, or with a saddle-shouldered sweaters is considered old-fashioned and stuffy in 2022. A zip vest kills that sense by more than a half. If it allows me to look more normal taking out the trash or getting the mail, then Midtown Banker overtones be damned.
Rugby shirt: Good overall, but let's face it, not seen too often these days, and can be considered "weird" by the masses.
Western shirt: Theoretically a good choice to dress down an otherwise formal(er) outfit, but I don't own one at the moment. So can't speak from lived experience.
Zipper coats: Baracutas, Barbours, Filsons: I'll take them over Canada Goose and North Face any day. Also the Vietnam army field jacket (M-67?) when worn with otherwise formal ensemble (I think this is one of Simon Crompton's original examples) Truth be told they are getting rarer by the day, but they are the best I can come up with.
Ball cap (3 seasons) or beanie (winter): Not only casual and common, but handy if you can't be bothered to apply hair product during these WFH times.
Hawaiian shirts: I like popovers with button down collars, but this option seems to be summer-specific. Ditto tennis shirts and shorts.
Footwear: This is tricky if we wish to be traditional all the time (I say no running shoes unless actually running). I think suede is generally better than shiny (because if you have say calfskin you brush often and polish periodically right? that gives luster that sadly sticks out in 2022). I'm partial to dirty bucks (can look like white/beige tennis shoes from a distance), low-contrast saddle shoes entirely in suede or nubuck (easier maintenance is a plus too). Blue suede comes in handy with darker trousers. Not to leave out boat shoes, Bean blucher mocs, loafers and the ilk. Wear LL Bean hunting shoes whenever it's wet enough (they are comfy too with thick socks). Perhaps the Red Wing Moc Toe boot is also a good idea? But I doubt it, and I'm not interested in adding it to my collection.
To be honest it's hard not to stand out when others are wearing Nikes, crocs, flip flops, and lumberjack boots. But I think my choices above beat cordovan longwings and captoes, and hopefully people don't look down as often.
So these are just some thoughts in no particular order about strategies to ensure we can still wear heydey Ivy League clothes as often as we can, and not look too outlandish when "out and about" in public in 2022. Feel free to engage, flame, or glorify
