Dress Like A Man: The Anti-Douchesuit

I have had a lot of interns ask me where I get my clothes. This isn't surprising, since I look great all the time. I tell them, "I don't get all my clothes in one place, idiot." And then I tell them some version of the following:

If you're a male in his early 20s who wants to look good right out of the gate at his first real job, you probably need help, since the vast majority of young men either don't give a fuck or think that dressing the same way they did at fraternity semi-formals is appropriate. From now on, sorry to say, you've got to save that shit for the golf course.

You need a white button-down, and not just any white button down you find at a church bazaar. It needs to fit you. Not like this:

Like this:

Get 10 of these and wear them in a constant rotation. To keep the pits fresh, use baking soda, hydrogen peroxide and salt.

Wear a white v-neck underneath. I recommend Alternative Apparel, but whatever you do, just don't get Hanes. There will come a time when you spill something on your shirt and need to remove it immediately to begin spot treatment. You don't want to be caught in a ratty rag that your grandfather or a homeless person would wear.

There will be those who disagree, and of course they're wrong, but I think a trim fit suit is the best way to go. For people like me who have rippling biceps and jacked thighs, there are tailors, but the overall purpose of the suit's cut will be the same: to look like you belong in this century. You have a phone that fits on the inside of your coat; you don't need Gordon Gekko pants.

I wear this most of the time:

Along that same logic, don't wear a hat. Just don't do it. Internet memes have ruined every type of full brim hat there is. You'll look like a douche. If you're running out of hair, shave your head and grow a beard.

Shoes: one pair black, one pair brown. No weird leathers. Wingtip oxfords and you'll be fine. Resist the temptation to wear a penny loafer. Never wear sandals. If you think I mean just in the office, I don't think you will benefit from this post. Never wear sandals in life.

You socks should be a Polo argyle, with the understanding that people shouldn't notice them. If they do, your pants are too short.

I understand that not everyone is an Adonis who can wear clothes effortlessly. If you're a plumper older man, that can work to your advantage in a way it never could for a broad. Wear a suit that fits you and carry yourself with brash privilege.

If you're a plumper man and you're still in your 20s, however, you can (and should) lose weight easily. Stop drinking beer, join a gym, and suppress all the memories of your childhood that cause you to binge on Kit-Kats in a Xanax-induced somnambulent stupor. That should do it.

Oh, and you aren't a child anymore, so get a Rolex.

 

For more casual days (weekends not at the office) I suggest going to Kohls.

I have these $10 V Neck type shirts which are super comfortable and cheap. I have one in each color.

"It is better to have a friendship based on business, than a business based on friendship." - Rockefeller. "Live fast, die hard. Leave a good looking body." - Navy SEAL
 

I prefer comfort, minimalism and style over just throwing money at things personally. A $10 shirt does the same thing as a $100 shirt when I'm walking around downtown at the dog park.

"It is better to have a friendship based on business, than a business based on friendship." - Rockefeller. "Live fast, die hard. Leave a good looking body." - Navy SEAL
 

Rolex's are fine, just you have to ditch the metal bracelet and get yourself a high quality leather strap.

Follow the shit your fellow monkeys say @shitWSOsays Life is hard, it's even harder when you're stupid - John Wayne
 

I know it isn't a huge deal at that price point, but if you are someone who lives an a hot area and you sweat or you rest your wrist on the counter, you will blow through straps like nothing. Shit aint cheap.

...
 

Most of this can be remedied if you quit buying off the rack. A good tailor will walk you through all of this. I know some of you are on a budget, look at Suit Supply, Indochino, Black Lapel, Thick as Thieves, etc...they are all generally comparable made to measure for around $500-$1000. Step up to a better brand when you get through that first or second year.

 

Well we can put you in the boring person category. Also you need more that 2 pairs of shoes, period. At minimum one per work day.

Follow the shit your fellow monkeys say @shitWSOsays Life is hard, it's even harder when you're stupid - John Wayne
 

Shoe game seems limited. Only wing-tipped oxfords?

Personally, I think you should avoid wearing brogued shoes to the office (edit: if you work at a bank, fund, or any other place with a more formal/conservative dress code), given that it may be a tad informal in case you have a surprise meeting with heavy-hitters..

Get yourself a pair of:

Cap-toe oxfords in brown and black

Long-wing/Wingtip oxfords, with no broguing, in brown and black:

And of course, a nice pair of double monks, in brown and black. Cap toed-double monks (as in the picture) work very well for the office. Wholecut ones are great too:

Guide to what I mean with toe-styles: http://104.131.48.255/wp-content/uploads/2014/03/dress_shoe_guide_gm_to…

Brown shoes would look great with the outfits the OP posted. Choco brown/Dark Tan double monks or cap toe oxfords would be perfect for that navy suit.

"Be the Disruptor, not the Disrupted" - Clayton Christensen
 

Eh, used to be cover Equities at a fund with a buttoned down culture. Moved to a VC with a similar dress code.

Also I work in Asia (and not an early stage VC), we're not all soylent-drinking, college-hating, brogue-wearing Bay-Area dwellers.

"Be the Disruptor, not the Disrupted" - Clayton Christensen
 

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