If you live in a place like me where traditional stores to quench a sartorial thirst basically don't exist, your options are either the mail man and the Internet or an airplane. However, even if you lived in some of the places around the world that offer quality items for less than their ridiculous retail prices, the Internet will prove to be your best option. I divide the supply into two categories: web store sales and eBay. Most web stores tend to have their sales up at the same traditional times such as midsummer, but many offer goodies around the year. On the other hand, some price tags can be justified with their quality and can be well worth the investment on their RRP. For example, Equus Leather is a company that is offers bargains every day just at their regular pricing. Overall, shopping in web stores is quite straightforward and mostly depends on whether you can find the best stores for your taste. eBay on the other hand, is a completely different animal, and requires a bit more attention.
So, eBay. To start with you need to retain some of that common sense. Avoiding getting ripped off (although if you do get scammed after my text, that's not on me) is not too complicated. If the seller is someone with 0 or 1 feedback, the price too good to be true and the pictures probably a bit hazy and crappy, the alarm should be ringing. I personally don't buy from people with less than 100-150 or so feedback, but I must agree sometimes you tend to take leaps of faith. My latest L.B.M. 1911 jacket, for example, was bought from an Italian shop with only very little feedback and who spoke no English to speak of, but hey, I got the jacket (that I could not have gotten without going to Italy) and I got it for a good price. So, as you eat the hunger usually grows. As I can't say I haven't taken risks, I certainly wouldn't recommend taking them.
To avoid risks I would start with eBay stores. You can find tons of nice things just from these registered stores which often work like normal businesses. With them I would consider the risk factor to be about the same as buying milk from your local groceries. There are countless of eBay stores and big private sellers that often have more than 2000 (even 30.000 in some cases) feedback, offering probably trustworthy trading partner. Some of my favorites include elitebargainnyc, salsalocust, eyewearhut, sausages234, frieschskys, baleriac1 and retricker1829. You should save all the ones you think might have something for you, and check them at least twice a week, other of these days being Friday. Most bigger and more professional vendors tend to make their new listings on Thursdays, as then the 10 day auctions expire on Sunday evening, the time when most people are at home and by their computers.
Secondly, you should reserve quite a lot of time and patience to actually build your wardrobe with eBay. I would say that 2-4 pairs of shoes, perhaps a few jackets, a suit and maybe ten to fifteen ties is a realistic goal within a year. Expect to lose at least ten items you really wanted and "needed" with another few where your mobile internet cuts off right when you're supposed to bid. Even if you scour the supply as often as possible, it is only so often that you're going to find items you are really looking for, and when you do, the chances are you aren't the only person trying to win it. You can try using bots programmed to make the winning bid, but for sheer simplicity I would personally go without any bots at first.
Simply make a thorough list of things you are looking for, and then start searching. If you are located in Europe, go through the UK, Germany, France and Italy first. Most vendors in the EU don't mind shipping stuff within the Union, and the costs are quite reasonable. Furthermore, there are no added customs fees or taxes, so buying from these countries is basically like buying from your home country. The available items tend to vary quite a lot by the location, with majority of the supply being local and then foreign items here and there. For example, for English shoes go for the UK (Sausages, salsalocust) and for Italian odd-jackets and suits go for Italy. Simple. And if you don't speak the language, use Google Chrome and the translator and you should be able to make sense of the site navigation and so on.
Now, I would say that there are two ways of keeping track. First, when you search for items, you will start to find sellers that have bigger inventories and more feedback. If you find someone with a lot of different items you fancy, just save them and you will be able to check them easily afterwards. The benefits are that unlike when searching with a certain brand you will also have the possibility of finding other similar items the vendor might add. For example, if you're looking for a L.B.M 1911 unstructured jacket from Italy and you're also checking the sellers' own pages, you might find a completely similar Boglioli jacket that is just as good, if not better. However, if what you're looking for is more specific, like in the way that the only possible pair of black shoes you are looking for are a pair of Crockett & Jones Hallams, then go with the brand or model name.
As an additional tip, a good way to follow up on your saved searches (or the best in my opinion), is the eBay mobile, that always informs you when there has been additions to the results of the search of the given parameters. It also lets you quickly browse only the new additions, a feature missing from the normal web browser eBay, saving your time. A good way is to go through your searches with your phone once a day adding desired pieces into your watch list. Do this when commuting from work eg., and you'll find it a good way to spend the odd boring hour. You'll have more time to see what you added later in the evening. The mobile eBay app is also quicker to change between different countries'.
If you are buying from the United States, you'll find that the selection of especially Italian luxury goods is often better than here in Europe. It is easy to find good deals on such delicacies as Isaia or Zegna's premium product lines, and the American eBay is simply stuffed with Ralph Lauren and Brooks Brothers. However, be aware of the weakened euro that has driven up the prices for us quite a lot lately, and also note that the price doesn't include the taxes nor the customs fees that your local officials are going to bill you. Now, you may try asking for the seller to mark down the price (which I personally do not recommend), but this is against eBay regulations (some a bit serious sellers might turn you in) and also illegal, so at least the professional vendors most likely won't do it. If you live in the U.S., you will have enough things to buy in your own eBay for years, so I wouldn't recommend starting the overseas purchasing at first.
So, if you're new to eBay, start with building up and saving your searches and keep checking the eBay stores that carry the kind of clothing you are looking for. Fridays are a good day to do a thorough check as most bigger vendors add their wares on Thursdays. Be patient and don't rely on only eBay to build your entire wardrobe from nothing as it is by far the slowest method. On the other hand, it is also the cheapest if you know what you are looking for and also offers occasional finds that can’t be found anywhere else. Once you start to have the feel for the prices, you know what is cheap and what is not. Then you will also be able to make the decision without much research. A good example of a case like that was when I saw my Alden tassel loafers get caught in my search with a price tag of 39,99 USD – it took me about 2 seconds to hit the “Buy Now” button. To sum up then, the insanely good deals are quite rare, and when seen, need a fast trigger finger. However, if you don’t go searching, you’ll never find any for sure.