Where do I begin?

figure out what fits you. fit is number one above everything else that is important in style. afterwards, figure out what you have in your closet that fits and that is stylish. donate the junk. start buying staples that fit right and will last a long time. shoes, slacks, blazers, ties, shirts and so on. good luck.

Wear a lot of light grey.

The first thing you should buy is Dressing The Man by Alan Flusser. Perhaps more than any book out there, it explains how clothes work, or don't work, and it will save you tons and tons of time and money as you embark on what can be a maddening, frustrating and, ultimately, rewarding experience.

The question you ask--where do I start--is both obvious and nearly impossible to answer, and answers are going to vary depending on your tastes and goals. It's easy, for example, to say "Start with a navy blazer," because that's a basic that every man needs. But what kind of navy blazer? There are slew of them out there, with varying lapel widths and cuts. You need to decide between double vented, single vented or ventless. Metal buttons or a more subdued tone? Sack or darted? How much suppression should it have?

Don't worry if you don't understand half of what I just wrote, but don't go out and buy a blazer until you do. For now, just understand that something that's allegedly simple can be complex, and something as basic as a navy blazer involves a lot of decisions that are based both on personal taste and your body shape. What you don't want to do is end up with eight blazers in your closet before you finally figure out the one that's right for you, and, making matters worse, there usually aren't any "right" answers because a lot of this is subjective.

This will be very difficult to do, but go slow. Resist the urge to fill your closet in six months, and that urge will be very powerful. If you succumb, you are bound to make a lot of mistakes that will suck both closet space and your bank account. Remember that no item of clothing is a bargain, no matter what it costs, if it's not right for you and you don't actually wear it.

Read lots, ask questions here and elsewhere (Ask Andy About Clothes can be a helpful forum), study what other men wear. Be VERY wary of salesmen in clothing stores. Most of them know next to nothing about clothes and care only about making money. There are exceptions, of course, and if you are fortunate enough to find a store with trustworthy sales associates who know their stuff and will tell you the truth, then you will be very lucky. Nothing beats a personal relationship with a reputable haberdasher, and a good tailor is also indispensable. Good tailors will teach you a ton about clothes as you take in things for alterations. If you find a good one, stick with him.

Good luck.

+1000 to what pnutpug said.

 

For basics, most people here love Uniqlo (available only at a brick-and-mortar store in NYC, or through Suddenlee.com if you don't live in New York).  American Apparel, Alternative Apparel, Lands End Canvass, and Banana Republic are also good places for basics like sweaters and tees, but beware of the gaudy things at BR.

 

Since you wear dress shirts and oxfords a lot, you should probably make sure that they fit well.  If they are blousy (too much fabric), take them to a tailor.

 

If you have the money, bespoke (custom-made) trousers from a reputable tailor will fit you better than anything off-the-rack, especially since you are so tall. 

 

Pay attention to your shoes - they are very important.  Cheap or mismatched shoes (relative the the whole ensemble) speaks poorly about a man.

 

Best advice I can give you is to post pictures of yourself in these threads:

http://www.styleforum.net/t/253842/waywrn-mc-casual-style/2535

http://www.styleforum.net/t/234255/hof-what-are-you-wearing-right-now-part-iii/21315#post_5134619

That way, you won't have to decide on your own if your shoes are ok, or if your shirts are too blousy.  Also, going through the threads and reading lots of posts will allow you to gain advice vicariously through previous posters, some of whom probably started out like you.

 

Best of luck to you!

Dressing is really not important at all, no one cares too much as most people dress horribly. People are on here because they see it as a hobby.

Also, please trash all your polo shirts unless you want to look like a best buy employee. No one looks good in them.

I mean no disrepect at all to CDHagg, but I would never buy anything at Banana Republic or Lands End or American Apparel. That does not mean that he's wrong and I'm right. It simply shows that his tastes are different than mine.

See how weird and complicated this can get? If folks could come to blows on the Internet, they would over such subjects as Joseph A. Bank, which some see as a legitimate place to buy clothes while others, including myself, wouldn't step in there to buy anything but shoe trees.

The suggestion that you post photos in WAYWT is an excellent one, and it is also an excellent thread to peruse to see what others wear and read critiques.

Again, most importantly, go slow. You've emptied your closets. That's a good start. Now, if I were you, I would not buy anything (except Flusser's book) for one month. Mark the date on your calendar and spend the next 30 days studying up and deciding what it is you should buy. Not to repeat myself, but a navy blazer would be a good start. Besides being a wardrobe essential, you can learn a lot about clothing from buying a blazer that will come in handy when you step up to a suit. You could also set a goal of deciding whether you should go with pleated trousers or flat front, which is a relatively simple sartorial call.

Am I the only one who wonders if these 6'5, 6'6 guys asking for style advice are former NBA players?

Don't go out and buy a whole new wardrobe right now, because after another 6 months lurking here you may realise that you spent a lot of money on the wrong stuff. Take it gradually, lurk on this forum, read through some of the old threads (the "best of WAYWRN" threads etc ( here's 2010), the Anderson & Sheppard expatriates thread, the MC casual thread - I'm too lazy to find links, but just use the search function). Also stick to physical bricks and mortar shops to begin with - you can waste a lot of time and money buying clothes online.

start with good fitting fundamentals like a white shirt, navy/charcoal suit, and the rest will follow

I believe oxfords refers to his shoes. Not much a tailor can do with them.

Great advice to stick with BM when you are starting out, but the counterweight is that you need to spend A LOT of time researching things before you darken the door. Otherwise, sales associates will descend like locusts, leaving you broke and, in the end, without any wearable clothes.

Listen to this man. He is trying to save you time, money, and heartache.