How Not to Dress Like a Douche

Off Topic
1

I have problems finding clothes and need advice on how to widen my wardrobe and not look like a douche in the process.

Some background:

  1. I am very tall and borderline emaciated-looking at 275lbs. Yes, that tall and that skinny.

  2. I may be an engineer and geologist by training, but I am a cowboy at heart and literally have a barn in my backyard with horses. I like jeans, work boots, button down shirts or t-shirts.

  3. I wear Carhart flame-resistant clothes to work even though I am mainly in the office. I’ve been known to spray down old Carharts with scotch guard and go skiing in Aspen and leave my North Face at home because I don’t give a shit.

  4. I have suits and sports coats made that I will wear for special occasions. So dressing up is not the problem.

  5. Where I fall apart is dressy-casual clothing. My bride, while she loves horses, is a city-slicker. She wears Burberry, LaCoste, etc. She has attempted to dress me in this crap, but I look like a total Jersey Shore douchebag in it. Too tight, too short, too whatever.

  6. Her family likes to do social events in places like Nantucket, which is pretty WASPy for a bunch of Jewish people, but they like it. I stand out, literally, as the darkest-skinned guy on the island besides a couple of token NBA players who married white girls and look at lost as I do. I would like to blend in a little bit more.

Any advice besides PIIHB? I don’t care for the smell of shit.

2

I am in a similar situation. Barn in the back yard. Horses in two different locations. Always doing something horse related in my spare time. Wife is a preppy horse girl. I am a professional and I have to wear a suit, or at least a tie, every single day. I hate “business casual”. I would rather be at one extreme or the other. That in between stuff is where I have problems. My solution is one of our local Ralph Lauren outlets. You can wear a Polo button down with jeans and boots almost anywhere on the weekend and look like a damn boss. I prefer the white fitted dress shirts with the blue pony. They are cut bigger in the shoulders than most other off the rack shirts.

3

First thing is to find yourself a great tailor. Not someone that just replaces buttons and hems pants. Probably the best way to find a good tailor is to visit the high end suit shops in the area. Often these shops farm out all or at least some of their alterations. You want the guy who can make an off the rack Canali fit like it was cut and sewn just for you. Then visit the tailor and have a talk. He will tell you what to look for in off the rack dress shirts, golf shirts and pants of every type.

Tell him you want a working relationship with a tailor that can and will completely deconstruct and reconstruct any piece of clothing you bring him. If he is game, it won’t be cheap. But if he has the skills, it will be worth whatever he charges. Have him measure you top to bottom and write down everything.

Once you know your basic measurements - ie waist, rise and inseam for pants, neck, shoulders, chest, arms - both length and circumference at the bicep/tricep while relaxed and flexed and ideal length, then it is time to go hunting. Find shirts that fit in the shoulders, chest, and sleeve length and are long enough for your torso - tucked or untucked, depending on what you want. Find pants that are in the neighborhood for waist/rise/length. Start with a pair of pants, a couple of dress shirts and a couple of polo shirts in solid colors.

Take your finds back to the tailor and try on each item for him so that he can mark, pin and measure. I bring my tailor 3 dress shirts I find on sale that fit neck and sleeve and he will completely break them down and reconstruct for $100. Pants are about the same. He will also take in/taper golf shirts for about $20 each.

Once you have gone through the process a couple of times, it becomes a lot less painful to shop for clothes. More like root canal with novacaine, rather than without it.

4

I can only speak to what I do.

Almost every day I wear collared button down shirts. Most of them are either Geoffrey Beene or Banana Republic, and most are striped with a few solid. I’ve avoided the plaids. All of them are nice enough to wear with nice pants and a jacket. Mostly blues, greys, a few green, and then whatever color stripes: black, grey, green, maroons.

Then I have a couple pairs of subtly-patterned grey and black lightweight wool pants, that fit well. These I’ll wear when I need to be a bit more dressy. Also a pair of khaki colored pants.

The rest of the time I wear lightly washed jeans, a few lighter, a few darker. They’re neither tight nor loose. Brands that have worked for me are Lucky, J Crew, Buckle, American Eagle. Not all are the highest quality manufacturing, but they have acceptable style at an acceptable price.

I also have two pairs of shorts that actually fit well; one khaki, one grey. With a nice button down shirt, sleeves rolled up or not, these can pass wherever people are wearing shorts. I usually wear jeans in those situations, but I’ve made a few exceptions.

I swap out shoes depending on circumstances. Dress shoes work with the jeans, as do flip-flops.

In order of formality, with the same shirt for all of them:
flip flops and shorts; sleeves rolled up or down
flip flops and jeans; sleeves rolled up or down
“casual” shoes (loafers, boat shoes, driving shoes, nicer tennis shoes) and lighter jeans; sleeves rolled up
casual shoes and darker jeans; sleeves rolled down
dress shoes and darker jeans; sleeves rolled down
dress shoes and darker jeans; sleeves rolled down; jacket/sportcoat
dress shoes and wool pants; sleeves rolled down
dress shoes and wool pants; sleeves rolled down; jacket/sportcoat

I can, and have, worn the same shirt to go from dicking around on the beach early in the day, to a formal dinner that evening with my girlfriend in a nice dress, just by changing shorts/pants and footwear (and a little ironing).

5

[quote]kineticj wrote:
First thing is to find yourself a great tailor. [/quote]

I’ve got this. Suits, dress shirt, slacks, etc., are all custom.

It’s the business casual and “resort wear” that has me screwed.

6

[quote]thethirdruffian wrote:

[quote]kineticj wrote:
First thing is to find yourself a great tailor. [/quote]

I’ve got this. Suits, dress shirt, slacks, etc., are all custom.

It’s the business casual and “resort wear” that has me screwed.[/quote]

You can get jeans and khakis custom made. Probably corduroys and other casual pants too. I know you can have great casual button downs cut and sewn. Not cheap, but quality that should last. Might have to go to LA/Chicago/NY for the truly custom casualwear. I have several pairs of cords and casual pants that have been drastically altered. But I am only 6’2" so it has to be infinitely harder for you to find things that come even close to fitting.

I keep picturing you as a native american Jeff Goldblum trying to squeeze himself into a secondskin Lacoste polo.

7

I find that people who worry about what they wear end up looking like douche’s. Dress the way you want and don’t be a douche.

8

[quote]Rockscar wrote:
I find that people who worry about what they wear end up looking like douche’s. Dress the way you want and don’t be a douche. [/quote]

dude wears camp dry sprayed carharts to ski. I don’t think he is THAT worried about what other people think of his wardrobe. He just needs casual clothes to fit his lankyassed self.

9

[quote]thethirdruffian wrote:

Any advice besides PIIHB? I don’t care for the smell of shit.[/quote]

it’s all in your timing - mornings are no bueno, and right after dinner is bad.

about 3:15am and drunk as shit works best.

my $.02~

10

White t’s, comic book t-shirts, v-necks, and if it’s a fancy event I’ll wear a polo.

Haha, but seriously as long as you wear clothes that fit and take it easy on the accessories you’ll be fine.

11

[quote]kineticj wrote:

[quote]thethirdruffian wrote:

[quote]kineticj wrote:
First thing is to find yourself a great tailor. [/quote]

I’ve got this. Suits, dress shirt, slacks, etc., are all custom.

It’s the business casual and “resort wear” that has me screwed.[/quote]

You can get jeans and khakis custom made. Probably corduroys and other casual pants too. I know you can have great casual button downs cut and sewn. Not cheap, but quality that should last. Might have to go to LA/Chicago/NY for the truly custom casualwear. I have several pairs of cords and casual pants that have been drastically altered. But I am only 6’2" so it has to be infinitely harder for you to find things that come even close to fitting.

I keep picturing you as a native american Jeff Goldblum trying to squeeze himself into a secondskin Lacoste polo.
[/quote]

Thanks. There is a company called Willis and Walker that Saks carries for men between 6’6" and 7’7" so I’m right in their wheelhouse. I go to Houston periodically, so I will check.

Re: Goldblum – not hairy, not curly headed, and not ugly. Just tall.

But — I tried on a specialty size 10 “Tall” Lacoste Tennis shirt. It fit me like a half shirt — tight on shoulders and baggy around the middle, expose my navel. Dumbest thing I’ve ever seen.

Nike Golf allegedly has stuff, too.

12

I think a pair of well fitted jeans and a vneck tee shirt can look classy and comfortable. Maybe I am showing my age but if I can find a sports jacket that fits right, I think its a great look (jeans, solid color tshirt and jacket) . I also like a fitted henley and jeans as well. To me these styles are classic, never go out of style and works for any body type.

But I also wish I can wear sweatpants and a thermal tshirt everyday

13

Wait…how tall are you? I am having a hard time picturing anybody looking emaciated at 275lbs.

15

Wear what you think you look good in or is comfortable. Second choice wear what everybody else in the immediate vicinity is wearing. Problem solved

16

Most Native Americans I know have super wide feet which is problematic sometimes…

Try Van’s classic slip on shoes, big variety, not flashy unless you go for those colors/patterns, and they are squat shoes.

Jeans, your junk doesn’t need to be plastered to your legs when you wear them. Try 2-3 waist sizes larger than you are used to cowboy, keep the length the same or one inch longer.

Shirts, you should still wear button downs just different materials and patterns, short and long sleeves. Roll your sleeves to change it up/ show off the guns or whatever. The third style of rolling stays put, little harder but they wont roll down. 3 Ways to Roll Up Your Shirt Sleeves - YouTube Try unbuttoning the top button or two…

Try to wear shit that feels comfortable and you will look it in your clothes.

17

I wear button downs and jeans a lot. I live in Florida and with two or three buttons undone and the sleeves rolled up it’s more comfortable than t-shirts. It’s right at the dressy-casual thing you’re looking for and you seem to like stuff like that anyway. If you want to get WASPier go for some Polo stuff. I’m white and trust me, Polo drives white people crazy.

18

If you can’t beat them join them.

19

[quote]thethirdruffian wrote:

[quote]kineticj wrote:
First thing is to find yourself a great tailor. [/quote]

I’ve got this. Suits, dress shirt, slacks, etc., are all custom.

It’s the business casual and “resort wear” that has me screwed.[/quote]

Resort wear:

Khakis, I like bonobos boot cut not sure about your size being available though?

Button down polo

Driving moccasins or boat shoes no socks

Business casual:

Same khakis, or any business casual pant just avoid pleats

button down shirt, I avoid wearing shirts with logos showing in a business casual environment.

a stripped down business shoe, but with more of sole compared to the boat shoes and moccasins. With socks

20

You are a 7 ft Apache.

You will stand out no matter what.

If you tone it down or try to blend in it will be painfully obvious.

If cowboy is your style just go with rich Texas cattle rancher if the situation warrants it, that way you dont disrespect their venue but you are what you are what you are.