Be a Smart Sales Shopper

Many people are happy to buy items just because they are cheap ("wow, sneakers for only $20"). However, the actual value might be less than the price, if an item worn has a negative effect on the buyer or is rarely or never worn. In other words, the purchase was a bad decision. Too much wishful thinking, guessing, and impulse buying often happen. Meanwhile, as a rule, stores want to make as much money as they can. Which means the better items usually are discounted less.

The Reality of Sales.
Flash sales (lasting a few hours) work on pressure to act instead of think.
Spend x and get a discount or free shipping is okay if already considering spending about that amount of money.
Going-out-of-business sales are likely to be lacking in good items by the time discounts are big.
Sometimes discounts are because the items were being returned (poor fit) and problem solved for the retailer because Sales items are not returnable (Closeout/Clearance, usually).
Recurring major discounts on store-brand items suggests those items are not as good as the regular price indicates - the money being saved is partly an illusion. (If, for example, all suits are being discounted at a seemingly random time, that suggests a recurring sale.)
Two-for-one deals are okay for underwear, socks, and maybe pants, but not okay for most other types of attire because that leads to noticeable repetition and possibly two unsatisfactory items instead of one. Also, quality items in any category seldom are sold in multiples.
Online discounters selling unusually low-priced items from fancy brands might be selling fakes. Sometimes they are legitimate, with the items being from previous seasons, which usually is fine if one is not a fashionista.
High-end stores' generous discounts might be less than they seem; look at retailers with lower regular prices.
Outlet stores increasingly carry clothing that was made specifically for outlet shopping, i.e., the deals might be worse than they seem. Also, some items might not be less than at the regular stores.
Very discounted brand name items (not sold directly by the maker) - lower-quality diffusion lines or from the previous season?
Large discount on a limited number of items - why? A brand is no longer being carried? (Usually not a good sign as to customer feedback.) The line is being discontinued or has been replaced? Fit and materials might have changed slightly - compare with the current line.
Outdated athletic sneakers might have inferior features and might even be slightly structurally degraded due to aging.
Unboxed footwear sold in discount stores might have been tried on so much that damage or contamination has occurred.
Online coupons often can be stacked on top of online sales. (Search for them.)
Shipping and travel costs, as well as taxes, must be factored in to the sales prices.
Sometimes it pays to group a few purchases together, even if some individual items are slightly cheaper elsewhere.Foreign transaction fees and import charges might negate savings in some cases.

Before the Sales Start
Have a strategy before looking (priorities), including specific wants and needs, estimated amounts for various items, and total maximum amount to spend. (Know how much money there is to safely spend.)
Look online first. Be familiar with retailers and style.
Ideally, research on an expensive watch or a particular line of suits or dress shoes should be done before purchase; do not feel pressured to guess on such important items. (And know the little details that make proper suits and dress shoes. There are many imposters out there.)

Worth Buying (Appearance and Fit)...?
Strange sizing is common among Clearance item shirts - maybe one is unusually large for a size Medium.
Unusual natural fabrics can be a positive, though usually not where dress codes exist.
Weird hybrids (such as a cross between a suit and a tuxedo) often become sales items.
Styles that are losing popularity eventually are sold for less. Some potentially will be viewed negatively, for example, squared-toes shoes as today's bell-bottoms.
Items with minor flaws are supposed to be labeled (for example, as seconds). They might offer great savings, but they are not a good idea for important situations, such as interviews.
Colorful pants usually are a bad idea (for men), especially if quite slim-fitting.
Jeans that have noticeable designs or are not in medium or dark blue are risky.
Clothes for non-athletic wear that have large amounts of synthetic material almost never are worth buying
Cashmere discounted to very low prices usually means low-quality cashmere that will deteriorate quickly.
Leather priced very low almost always is low quality, often visibly so to some people.
Poor fit is not a bargain. It has hidden costs.
Inspect carefully and, if possible, try on. (Try on with layering if that is how an item will be worn.)
The item should fit well or at least tailoring to accomplish that should be cheap (and not skimping by having a drycleaner attempt to make major changes). Casual shirts should have descriptions and pictures that give confidence about the fit. Because there is much variance in shirt fit and tailoring is not always possible.
It is risky to buy shorts online without having a clear idea of the length. (It almost never makes financial sense to tailor shorts.)
Do not buy outerwear, sport coats, suits, shoes, sneakers, or eyewear online without first making almost certain the items will fit well, like trying on in a store first. (Do not assume that a local store stocks and has on sale the exact item sold online - if not sure, call.)
Does the store offer minor free alterations?
Read online reviews from previous buyers (but keep in mind that some websites might block negative reviews).
Search online for the same item (price comparison and more).
Care instructions for casual clothing should be listed and followed; required professional cleaning often is a poor investment.
Is it a possible buy at full price (if affordable at that price)?
Wear with what, in what circumstances?
The item would be replacing what, if anything?
If not happy with the color, pattern, or some other detail of an item that is not a need, chances of ever feeling satisfied when wearing it are low and therefore it probably is not worth buying. (Especially if not happy after trying it on and a minor, fixable fit issue is not the problem.)
Worry about negative reactions to an item's design usually is baseless, unless it is quite feminine, virtually costume, or possibly offensive.
If uncertain and it is practical to wait until the next day, make the decision then. (Always know when a discount ends and, if possible, whether the item in the right size and color or pattern is well stocked.)
If undecided on a temporarily discounted item and it is a physical store, it might be possible to have a salesperson honor the price after the sale is over.
If it does not feel right or is a compromise in some way, there often will be a better choice.
Risks are only worthwhile for inexpensive items.

Bonus wisdom
Do not shop as a hobby - perhaps read instead - and place a time limit on needless shopping.
Avoid shopping when tired or even slightly intoxicated. Mental impairment leads to purchasing mistakes.
Unsubscribe from retailer mailing lists if their sales are tempting without providing good value.
Shop with a spouse who might discourage possible purchases.
Know the return policy - who pays for shipping, store credit, restocking fee, etc. (If the retailer is located far away, that could make the purchase more risky.)
It usually is not a good idea to buy many items at once, for reasons of storage space and not suddenly changing one's look.
It is not wise to quickly buy many items from one retailer if it has a narrow aesthetic or noticeable branding.

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