Senior Digital Writer
Make a game plan. It helps to assess your closet before you do any shopping, so you can decide where the gaps are in your current closet. Nothing's worse than coming home from a shopping spree with five new button-downs, only to discover that you own several near-identical tops you'd simply forgotten about. Decide which pieces you need most—heels, denim, swimwear—and aim to find those first at the sale you're hitting.
Set a budget. Decide how much you're willing to spend before you head out. Does this mean you have to stick to your plan down to the dollar? Of course not. But having a general guideline will keep you from going crazy once you spy all those discounted duds.
Shop in the off-season. If you really want to save big, shop for items that aren't currently in season. You can get great deals on cashmere knits and leather boots around April or May, for example, and save a ton on swimwear during the autumn months. Of course, in doing so, you risk picking up something that'll be outdated by the time you're able to actually wear it, which brings us to our next point...
Invest in the classics. Sure, those 60-percent-off leather drop-crotch pants are Bieber-approved and carry a major designer's label, but are you really going to wear them? Ever?! If you can't picture yourself wearing the item you're eyeing for at least two years to come, put it back. Sales are a great opportunity to stock up on timeless must-haves—great denim, luxe knitwear, etc.—so look for those instead.
Dress accordingly. Yes, what you wear on your shopping mission matters! In general, it's a good idea to dress in separates—say, jeans and a tee. That way, if you're trying on a top, you already have the bottoms to team it with; if it's a skirt you're taking for a spin, you can see how it looks with a basic tee. On the other hand, if you're off to a sample sale, keep in mind that you might be doing your trying-on in public—and in the middle of a crowd. Leggings and a formfitting tank, in this case, are your best bet, as you can try pretty much anything on over them. As for accessories? Go for shoes that slip on and off easily (ballet flats or smoking slippers work well), and choose a crossbody bag that leaves your hands free to rifle through the racks and carry armloads of clothes.
Personal style is paramount. Typically, tons of trendy pieces wind up on sales racks because—surprise, surprise!—they don't work on everyone. If something's all wrong for your body type—a fact that should quickly reveal itself in the dressing room—you'll probably never wear it (and never should, for that matter). The same goes for items that clash with your sense of style. Never, ever wear pencil skirts? Guess what: you won't wear one that's 75 percent off, either. In general, if you wouldn't buy something at full price, you shouldn't buy it on sale.
Size matters. We'd say flat out that you shouldn't buy anything that doesn't fit—but of course, there are exceptions to this rule. In general, it's best to avoid "motivational buys"—pieces that are a size or two too small, in the hopes you'll eventually diet your way into them—but if you fall in love with something that's a bit big on you, a tailor can alter most anything to fit your frame. Of course, such a situation raises the question: if you must have the item in question professionally tailored, is it still a smart buy?
While the waists of dresses, skirts and pants can be easily altered, as well as the length of pretty much any garment, it's my personal experience that blazers, coats and jackets really do need to fit you straight off the rack—altering them is expensive and often doesn't work out.
If you're obsessed with a pair of shoes that are an absolute steal but half a size too big, you can usually add gel insoles or heel grips to make them fit. Buying too-small footwear, however, is a gamble. You might be able to have them slightly stretched by a cobbler, but this process doesn't work on every type of shoe (patent leather, for instance, is notoriously tricky to stretch). And be sure to try on your shoes for at least five minutes prior to buying—preferably on a non-carpeted surface, since carpeting tends to make shoes feel deceptively comfy. Remember: if they hurt in the store, they'll kill once you wear them out on the street.
Compare those prices. Those Alaïa sandals might seem like a steal–er, relatively speaking—but if another retailer currently has them in stock for even less, wouldn't you like to know before you invest? Use your smartphone to Google big-ticket buys before you pay—just to make sure you're not forking over a dollar more than you should.
Know your return policies. Many on-sale items are only returnable for store credit; if this is the case, make sure you could easily find something else at the shop in question that you'd love to own. In some instances, sale merchandise isn't returnable at all, which is why it's important to check any prospective purchases for stains, snags, sticky zippers or holes before you plunk down the plastic. Remember: these pieces have likely been on the sales floor for months, meaning they're probably been tried on dozens of times. Do a quality check!
Become BFF with your salesperson. Love a particular boutique or label? Make friends with the staff. They're the authority when it comes to upcoming sales—and might even tip you off if the full-price heels you're eyeing are about to be marked down. It's also not unheard of for shop staffers to set aside prime pieces just for their favorite customers.