Wardrobe refresh. Need your help.

First off, burn all your clothes on the sidewalk. Everything, down to the last fiber. Don't worry if the nylon melts; let the fumes be the gateway to your new sartorial vision. And if you could film the act and post it here. -- We'll wait.

Secondly, now this may sound shocking because I assume you are not a Junker of a member of Edwardian Society, but monocles are coming back. Everyone is going to be wearing them this summer. Don't believe me? People still wear Uggs. People do weird things, but a monocle is perfect for you. Go buy one and post a photo.

Next, your hair. Shave it off. All of it. Now get a white t-shirt and post a photo like a German Mr. Clean. -- OOH you are snaaaz-aay!

Have you though about an all-bridal leather wardrobe? You should. I'm sure the folks at Saddleback Leather can whip something up for you. Write them now, and don't forget to post the awkward conversation here.

I was wrong about your hair, luckily this year powdered wigs are back. You should get one before Geo. Washington's birthday. Note: use only artisan-made lead-powdered wigs.

There you go. You look nice and confident now.

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Seriously, your goals are reasonable. Unfortunately there is no one authority on what you should do. Read the forum as there are many posters with taste and can be followed as examples . Update your wardrobe slowly being aware of fit, and what looks good on you. You may want to pick up Alan Flusser's book Dressing the Man or some such style guide.

I would cut the number of items on your want list by at least two thirds. Here's my take:

Welcome back BlackBeard.
I would recommend performing this transition in stages. Begin with donating anything beyond your essential needs. Get rid of pleated pants and shirts with tired collars. Purge any ties that are never worn or see if you would like to start wearing them. Then spend a month to re-familiarize yourself by browsing on and offline. Form a plan to purchase new wardrobe essentials in stages according to your needs and priorites. This will keep you from impulse spending. A nice sportcoat, a few pair of shoes, socks and shirts will breathe new life into your style preferences. In fact, were it me, I would start with a dozen or more new pair of socks, exploring colours and patterns I previously overlooked. Then I would purchase at least 2 or 3 new pairs of shoes. The next purchase would be a sportcoat. These items alone will refresh things. Then refine further with new shirts, etc. New undergarments are also a pleasure to wear. You may find that you are not in need of an entire overhaul, but some simple tweaking.

Good advice from Ivar and Mol so far.
I would add that navy and charcoal pants are not as useful as you might imagine (there is much discussion of this elsewhere on SF that you could look up). But follow MoL's advice to take a bit of time researching and thinking before buying anything. You mention that you don't wear the cashmere SC because you lack shirts, so that seems a good place to start (you'll have the same problem with any other SCs or suits that you buy after all). I'd get half a dozen decent staple shirts from somewhere like Charles Tyrwhitt (but then, I really like shirts) - steer clear of anything more patterned than a basic stripe for now - and start wearing your cashmere SC a bit more. You don't talk about shoes much, but they are an important part of your wardrobe, aim to get a couple of pairs. See how you get along with that and reassess.

Congrats on the decision to start rebuilding your wardrobe. For $2,000-$2,500, it might be tough to do all of that well. Here are some thoughts. First, try to be patient and wait for things to go on sale (at least say 25% off). It will make this a lot easier. Also, places like Filene's Basement and Century 21 can be your friend.

- Charles Tyrwhitt shirts can be obtained for $50 per shirt on a regular basis. Skip the black label; the basic shirts are fine for now. Try 8 for now (6 solid, 3 pattern, save the additional patterned shirts for when you have more). This will be $400.
- +1 to everyone who said that medium grey dress pants are the best option. They will go with a navy blazer and look great with almost everything. Brooks Brothers on sale is not bad here, maybe take a gamble on Sierra Trading Post (great with returns if sizing is off). You should get 3 pairs for $300.
- Casual pants should be versatile. I prefer chinos in the stone to tan range; save the fun colors for now. Sierra Trading Post is another good option here. Feel free to search the forum when doing diligence on brands. 3 pairs for $150.
- I'm not a sock expert, but you can get good deals in discount stores. Get a couple more pairs. $100 for 8 on discount.
- For belts, my best guess is that you can probably score 2 good ones for $150 at a reasonable sale.
- Navy Suit - This is great to have for any interview, wedding or evening event where you do not want to wear pinstripes, which should stay in the office. Brooks Brothers regularly has sales for $700 or so on their 1818 line. Other comparable values exist. For maybe $850 or so shipped (maybe a bit less but don't quote me), you can get a basic MTM suit from MyTailor. Let's use $800 as a mid-range estimate for this. You want your one navy suit to look good when you do need it.
- Navy Blazer - Hang onto the cashmere jacket for now unless you want to get rid of it for some reason. Save this for the next stage of upgrades.
- Tie Bar - Not just yet.

Total is $1,900, give or take. I'd add two pairs of Allen Edmonds or comparable dress shoes. One black balmoral with some toe medalion (technically you should wear a plain stich cap or very similar shoe with a suit, but it is silly for you to have a pair of shoes that is too formal for most of your outfits; better to have something that can work with a suit and the rest of your wardrobe) and one brown or black blucher or monkstrap. These will be a bit over $300 each at retail, but you can sometimes find deals on some models.

$2,500, give or take.

This does not strike me as good advice at all.

Two shirts is not enough to allow for washing
One pair of trousers does not constitute any form of rotation
No belts? Most RTW trousers require belts.
Why no leather watch?

Recommend ignore this advice, your original suggestion was a good start.

Your goals seem reasonable, except for the suit, which I might curb until later. Perhaps don't spend all of your kitty at once and put the remaining balance into a new suit fund and slowly add to it. You're also not going to get a reasonable watch for that price, so definitely curb that.

Do you have long legs and a short torso? I am taller than you and have a shorter inseam than you, which seems strange. If you're going for a complete overhaul, ensure that your measurements are spot on.

Lastly, if you're going to be spending between $2000 and $2500, go to NJ to save on the sales tax. The difference is about the cost of another shirt.

Some potential Options:
- MTM - use some of the forum darlings for your shirts to get the best possible fit: Luxire is one that I've yet to try, but have been blown away by the results. Modern Tailor, I have used, but find the results to be very mixed. 10 shirts should run you $600-$750
- Scour B&S. Steve Smith gets massive amounts of Brooks Brothers at a great deal, so his presence can save your wallet. Assuming he gets items that fit you, he is a pleasure to work with. You should be able to find all of the pants that you're looking for in his sales. Since you work in the city, you can easily go into a Brooks Brothers and surmise your size.
- Scratch the green idea, because you also need to consider seasons, which I've not seen from you. In NY, you're going to go from heavy tweed to a tropical weight wool, so you'll need closer to 8 pants than the 6 you have listed. It is the tail-end of winter now, so perhaps only one tweed can carry you through, go for grey.
- Century 21 was a great suggestion. It can be very hit or miss in there, but usually it is more hit, especially for odd items. If you can go during lunch, it is better than going on the weekend, when it is far too crazy.
- You might be able to get the navy blazer from Steve Smith, otherwise perhaps you'll get lucky from RLBL, which seems to fit you well.

Good luck!

So I'm not as experienced as most people here, but I have been building a complete new wardrobe for about the past 18 months, and I'd suggest not getting everything all at once or too quickly.  Especially if you're not super knowledgeable about how things should fit or what is appropriate for your frame (off the rack), I would get just one or two of each type of garment at a time and see how I ended up using them.  That way, you'll see what works for you and what you want more of, and avoid blowing your entire budget on something you're sick of in three months.

This is exactly my idea.

I presumed that OP keeps some of his old stuff until he gets to replacing it. Sorry if I was a bit unclear about that.

Regarding the belt thing. No properly fitting pants -- RTW or otherwise -- should require a belt. If they do, either size down or have your tailor take in the pants at the waist.

If a pant has belt loops, it requires a belt.

Aesthetically? Yes. To stay up? No. In any case, your tailor can easily remove the belt loops, so their presence shouldn't affect your decision either way.

...

Not one of the lengthier replies is free of poor advice. The correct ideas voiced above are to not buy everything in a short time span, not buy as many dress shirts, skip the tie bar, and probably get two pairs of lace-up dress shoes. Some new advice: the Banana Republic shirt probably should be replaced, on quality alone, and also the Penguin long-sleeved shirt, if it's for business use. For brand recommendations (beyond Brooks Brothers and such for pants), etc., to be safe, pictures and other information should be provided. This company knows the subject very, very well.

+1