Here’s our confession/boast: almost everything we own was bought on sale. Our favorite Iisli sweater jacket? Tried it on at Bergdorf’s when it cost $430, snapped it up at a winter sale a few months later for $150; then loved it so much that we bought another one on HauteLook for $125. We’ve gotten pants from Banana Republic for $6.99 and worn them a lot. We once snagged an entire ball gown at an outlet store for $20 and wore it to our firm’s black-tie gala. Alas, most of these amazing takes came from the days when we shopped the stores really regularly — since then, we’ve had to adjust our shopping habits for a life where a) we’re usually, you know, working when the stores are open and b) it’s harder to set aside time on the weekend to shop. (Pictured: “Closing Down” Sale 2, originally uploaded to Flickr by johnthurm.)
(A caveat before we start our tips — in our minds there is a difference from buying good clothing at reduced prices, and buying cheap clothing. Personally, we have serious ethical issues with shopping at stores that specialize in knock-offs. (Hat tip to Counterfeit Chic, who covers the issue regularly.))
1. The next time you’re actually out and about shopping, do a little legwork — learn your size in the brands you ogle online. Are you a 7 or 7.5 in Cole Haan pumps? Are you a size 8 or 10 in Tory Burch? If you figure this out it’ll be much easier to snap up sales when you see them, whether they’re at online discounters like RueLaLa or department stores.
2. Use online tools to help keep you aware of discounts. We try to point you to a big sale if we see one, but a lot of the best deals (60% off) fall in the “lucky sizes” realm, when very limited sizes are left. Particularly if you fall on either end of the “regular” clothing spectrum — an XS, a size 14 — then you should set up sale alerts because there are tons of great tools. We love ShopItToMe, and we’ve heard good things about Savvy Circle as well. ShopStyle can also be handy if you’re watching a particular brand of bags or shoes.
3. Don’t pay for shipping more than you have to. When we shop online, we haaate paying for shipping — it’s our number one pet peeve. If there’s a minimum for free shipping ($75 or $200 are frequent numbers) then we will almost always try to fill our carts with at least that amount. Bloomingdales had great sales recently and, the bag we wanted — a Treesje bag marked from $600ish to $180ish — would not have gotten us free shipping. So we also bought a pair of Ralph Lauren shorts marked to $8 (we never wear shorts, but we always pack them on vacations, so the price worked well) and a Kooba bag (also marked to the $190 realm) that we were curious about. We wound up returning the Kooba bag, but the Treesje bag and shorts were great deals, and we still got the free shipping.
4. Look for coupons before you checkout. We almost always check RetailMeNot before purchasing anything online; we also get a lot of e-mails directly from stores, which frequently come with coupon codes.
5. Shop off season. That Treesje bag we mentioned? White patent leather — it arrived the weekend after Labor Day, meaning we won’t get to wear it for nearly a year. That’s ok, though — when Memorial Day rolls around we’ll be salivating for it.
6. Know the returns policy. Particularly if you’re filling your shopping cart in order to get free shipping, you need to be sure you know how long you have to return items. Some stores are very friendly — for example, we bought a ton of white dresses from Nordstrom’s, on sale, when we got engaged — different sizes, different brands, etc. — probably spending about $400 on four or five dresses. Nine months later, when it was time to get dressed for the rehearsal dinner, we tried on the dresses and wore the one that fit the best; we returned the rest without hassle. (Just to clarify — we don’t recommend you stretch it out to 9 months on a regular basis. Rather, just know the returns policy so you aren’t surprised if it’s a 30-day policy and you thought you had 60 days.)
7. Be flexible on the sizes. While in #1 we advise you to know your size, we also advise you to be a bit flexible on size when you’re ordering online. A lot of great sales happen on clothes that have the wrong tag. So if you see a size 8 and you’re a size 6, if the deal is right (and returns won’t be a hassle), give it a try. (We would not necessarily advise this for shoes, though.)
8. Know what you wear regularly. Our weekend uniform tends to be black t-shirts and jeans, so we frequently check around for black t-shirts on the site that look worthwhile to us.
9. Consider buying multiples. If you see a deal on something that you already know and love, consider buying multiples, either in the same color or a different one. We already mentioned our Iisli sweater, but we’ve done this a number of times — jeans, shoes, t-shirts, even bags.
10. Understand that some things just don’t go on sale, while others might be able to be negotiated if you’re buying in person. For example, we’ve never seen a classic Louis Vuitton bag on sale, and proudly bought ours at the store for full price. On the other hand, they say that jewelry can be negotiated — for example, if you’re buying a good watch (Cartier, Rolex, etc.) from a reputable store it’s not uncommon for the sales person to give you a 15% discount.
Readers, what are your best tips for getting steals online? Any victory stories you’d like to share? Also: if you like this story, please consider “Digging” it: 
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