The Contender

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HOUSE STYLE: TRUSTED COUNSEL


The Contender deals with a variety of esoteric topics, including my traumatic experiences with the Minnesota Vikings, which are not going well. But, if we’re honest, many of us are here for the clothes. And more than just clothes, but theories, rules and advice. So let’s get down to it, lads.

Naturally, there are no iron-clad rules in dressing, but never show your toes anywhere you can’t swim. Here are some guidelines that might help clear your mind. I’m generally wary of trends or any wide-ranging scheme espoused in a magazine. They’re trying to sell you something and trying to do it many times a year. I like things that outlast the temporary high of newness. I wouldn’t buy something I couldn’t wear five years from now. That keeps you out of the fluctuation of the overheated ideas that will quickly be discarded by the very people who popularized them. People who are trying to get you to buy clothes every three months do not have your enduring interests in mind. And before you take any advice from a sneaker expert ask them to show you a photo of what they were wearing five years ago. That should put things in perspective.


Some thoughts, in no particular order.

1/ You don’t need words on your clothes.

2/ A pink oxford is easier to wear than you think.

3/ Small collars only flatter the proportions of slightly built men. 

4/ Large collars balance out the proportions of the rest of us. 

5/ Wear anything three times before you abandon it (unless it’s shiny). 

6/ Never buy a hat or glasses without trying them on first. 

7/ A good overcoat? Definitely. And keep it.   

8/ If something doesn’t fit get it altered, otherwise give it away. 

9/ Don’t look for a dress shirt when it’s the evening in question.

10/ Your build dictates the fit of your clothes, not a prevailing trend. 

11/ No social situation is improved by being the worst-dressed man in the room. 

12/ Better to not wear a pocket square than to look like it landed on your coat against your will.  

13/ Don’t be remotely underdressed at a wedding. 

14/ If your sport coat arrived with a pin in the lapel remove it at once. 

15/ You shouldn't look like you’re wearing anything for the first time. 

16/ A stiff-collared dress shirt should be buttoned up all the way. 

16a/ If you want to keep your collar undone get a shirt with an unlined, soft collar, like an oxford. 

17/ A well-tailored double-breasted coat is the best shortcut to looking put together. 

18/ Don’t experiment on the big night. 

19/ Clothes shouldn’t be funny. 

20/ No Windsor knots, please.


House Style is a regular series of guidelines to dressing well.