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items of clothing that make you cringe

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Red trousers on men, boat shoes (except on boats), bright madras, shorts worn with blazer ... basically most of what is called Preppy nowadays. Love the 1930s collegiate look though.

Red trousers.


A British summer staple for a man of a certain age and sporting persuasion.

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Smithy

I'll Lock Up
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5,139
Location
Norway
Cricket jumpers on people who don't play cricket.

And bowties for day wear. Whilst brilliant for evening and dinner attire, its obnoxious daytime cousin is basically how to look like a complete stuffed shirt or a total prat in one easy gesture!
 

GHT

I'll Lock Up
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9,796
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New Forest
Barefoot in open toed Jesus sandals. Worse, calf height wollen socks, worn with open toed Jesus sandals.The acronym FCUK. Frogmouth pockets on trousers. Polyester, although to be fair, the jury is still out on this one. Mixed with cotton it gives a durable and crease resistant look to shirts, and, mixed with wool, does something similar with trousers. This one might be at odds here: Contrasting laces on spectator shoes.
 

LizzieMaine

Bartender
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33,763
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Where The Tourists Meet The Sea
On men: pants worn below the natural waistline, especially if said man has a paunch.

On women: T-shirts with slogans announcing the wearer's availability.

I like bow ties fine, as long as they aren't big '70s ones that make the wearer look like a featured vocalist on the Lawrence Welk Show. However, they must be worn sincerely, never ironically.

I own and wear a baseball cap on occasions of great state, such as visits to Fenway Park,or pilgrimages to visit the World Series trophy. It's a regular regulation-colored team cap, however -- no novelty prints or colors should ever be worn.
 
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Sharpsburg

One of the Regulars
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240
Location
Maryland
Oh, come on. A kilt can be quite wonderful on a brough (sp?) young lad! I will not ever accept anyone over the age of 3 wearing pajamas in public in any way, shape or form!!!
 

Metatron

One Too Many
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1,536
Location
United Kingdom
There is a certain combo that seems to be popular on the sartorialist right now,
massive jacket with loud print, skinny trousers and shoes with huge soles.
It makes the wearer look like some kind of prehistoric bird...
 
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