Dressing appropriately

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So first off, I hate wearing shoes. They make me feel claustrophobic, so I wear flipflops. Same with tight clothes or suits; I prefer oversized t-shirts and baggy jeans for everything.

My problem is I am starting to get to a point in my career where I can't get away with that anymore. I need to buy clothes and casual shoes.

I hate malls, they are loud and stressful, but I don't live somewhere with online clothes shopping. So my question is how do men know how to dress themselves? It seems like NT types are born with this innate sense of fashion that I just don't have. I've had most of my tshirts and jeans for over 12 years but I need to start replacing them.

Any suggestions? Or a good website to learn how to plan outfits?

No idea. Many of my clothes are handmedowns or come from charity shops, or they are purchased new but are cheap prices. I rarely buy clothes. I have not had much of an income the last decade.
I mostly wear those drawstring type bottoms and plain teeshirts where nearly all of them I remove the labels. I rip the labels out.
pants I wear one or two sizes too big foe me and socks are an issue if the tops are too tight. I will wear them but not for long.
Shoes. I am a bit particular with shoes. I wear for comfort and prcticality. For around my immediate countryside local area I wear wellies which are budget ones but comfortable. I do have walking boots but they are a little claustrophobic. I tend to wear yjem on rare occasions when needed.
I have shoe type walking boots... They look a bit like a cross between a modern walking boot and a trainer. They are comfortable and practical. I wear tnese almoat all the time or my wellies.
I do have a pair of budget trainers my brother bought for me. He bought them when he didn't have the money. I was soo greatful for them. I have really good brothers.
Somewhere I have black shoes but they are very rarely used. I used them for funerals. They are stiff and hard through lack of use.
Oh. I do have cyxling shoes which used to have SPD 's on them, but as I never got on with SPD's as I cycle at an angle, I've gone back to toe clips and straps several years ago. One can't get cycling shoes these days without those horrible SPD inserts!

Go to YouTube and search for some videos on how to dress fashionably. You should be able to find some recent videos that will guide you in your quest. I found some there that helped me getting myself presentable casually for some volunteer activities.

I like to walk around inside my house barefoot. I wear shoes outside the home. I don't like shoes that pinch my feet. Shoes come in "normal" size and then "wide". So when I buy shoes that are wide, they allow my feet to breath and feel comfortable. I also found some style of shoes to be better. Thirty years ago they had a style of shoes called Earth Shoes. They were a revolutionary design but they don't make the exact same style today. There are some brands that are constructed better and last longer. One style is called Clark. They are good.

As far as clothing I tend to let my wife pick it. I am color blind, so I have a great disadvantage in color coordinating what I wear. So you might request some help from a girlfriend, mother, wife. Women are a little bit ahead of the game in this area.

I hate to interfere with your work on finding a good "look" but if this helps then it has been worth it.


Sounds like you need to get a more "businesslike" wardrobe...this is tough.

If you hate tight clothes you're not alone. I can't stand them. So what I do is wear a lot of vintage-replica stuff (I know, talked it to death) but men's clothing from 1920-1930 will have a nice straight-line appearance that fits a lot of people just fine.

Go to Darcy Clothing (a website you may like) and check out their poplin dress shirts, white, attached collar (apparently in the 1800s collars were removable.) It is a replica of a 1950s dress shirt, not a slim fit and not a huge baggy Oscar Wilde-style Victorian one. Classy as can be.
I wear their "cricket shirt" which lacks a pocket and has a very floppy soft collar, even though it is extremely heavy cotton cloth for a white shirt. It's basically Edwardian sporting casual. Extremely high quality stuff.

Regarding your pants...baggy jeans are a lot of fun in their way. Perhaps you will want to switch to a pair of high-waisted trousers. They are not as prone to cramping and they drape nicely. There are a few companies (Darcy, Old Town, maybe Luxire but I don't remember?) that will fix you up with a pair. Be aware that they went out of style in the 1920s and must be held up by a pair of button-on suspenders. You will need to also take them to a tailor and have the bottoms hemmed up to fit your regular length--this lets you customize a little bit, and get the look you want. It's super cheap and easy. I can do it myself on my antique Singer sewing machine so basically anyone can get this for you. Also, if you get afternoon wood instead of morning wood then it might help hide that. Sorry for the extra information.

Now you will need a jacket and/or vest. Most jackets from the 1970s on (barring the boxy, 3-button craze of the 1990s) have a tendency to cramp. My brother described them as being like the shell of a bug. So you will want to get a vintage-style one, preferably a sack coat.

Try to find an unlined one if you don't like that bulky feeling.

Confession time here--I cut up a 1990s woolen suit, probably an $800 one all handmade, to make a replica 1930s/1940s suit out of it. The pants are now high-waisted trousers with no belt loops anymore and the jacket is a 3-button sack coat without pads in the shoulders instead of the low-necked linebacker look with 2 buttons popular in the nineties. But once I half-line the top and get the sleeves figured out I shall continue looking like an extra from a silent movie--and loving it because the clothes are super comfortable and fit me.

Accessories--try getting a nice necktie, not too long. Vintage ties are cool but there are some mighty nice modern ones out and about. Pocket squares have a dumb name and a terrible look. Fountain pens are to be carried on the inside pocket of the suit, never outside, unless you are a seedy realtor with a fake Mont Blanc (I carry a Conklin self-filler these days so there's no point in showing off with a brand no one ever heard of.)

Watches--nobody is forcing you to wear a big ugly watch that looks like a manhole cover. You can wear whatever you want that is professional. Digital watches come and go, analog watches tend to stay in style, and pocket watches have never been made illegal...hint hint. An antique pocket watch is the perfect fit for Aspies.

With all this I must suggest you a hat. I don't know what you look like. Your username makes me think you'd be quite dashing in a tam. So here you go--

No neckbeard hats
No straw boaters or Panama hats after September 22nd until mid-May next year
Please don't buy a hat from a mall.
Top hats never looked good on anyone.
Flat caps are amazing but get the 8-panel kind, the puffier sort. They can be pulled down nearer the ears in cold weather. Also, they can look formal one minute and casual the next.
If you don't like hats, skip it! It's 2019 anyhow.
Also if you wear hats inside, please do not. Even if it is 2019 we have no excuse for ill manners.


Good luck! Hope you can develop a new look soon!

How formal do your work clothes need to be from now on? If really formal, then just having a few identical suits usually does the trick for men. However, if it's that line between really casual and very formal where a suit would be "too much", then that's a little trickier. As far as I know, bright colors and picture and/or text prints are not part of dressing formally. Some kind of pants and jacket of good material, collared, one colored shirt (remember to iron them if they have wrinkles) and neutral shoes... that's about it, isn't it?