Step 5: Go in the Morning, Late Night, or Early in the Week
"People forget stores hours are extended. You definitely want to go as late as possible or as early as possible," Joe says. "Mondays are great shopping—they're typically quieter.”
Do not attempt to shop on Black Friday. In 2003, at the Mall of America in Bloomington, Minnesota, every one of the more than 12,500 parking spaces was filled by 2 p.m. We say stop the madness and stay home.
Step 6: Enlist the Professionals
"Make relationships with salespeople," Jesse says. "They'll keep an eye out for you. Some will even do presale—meaning if an item is scheduled to go on sale later in the month, they'll ring it up at that price."
Then when you're at the store or in the mall, be direct. "They're there to help you," Jesse says. "Tell them how much you want to spend—you have to bottom line it for them.” If they're a good salesperson, he says, they'll be up to the challenge.
Step 7: Channel Your Inner Negotiator
If you're not shopping at a major retailer or chain store, don't underestimate the art of bargaining. When a salesperson gives you a price, your next move is to ask, "Is that the best you can do?" You might then counter with "And if I pay cash?" With these two little sentences, one O editor managed to get $200 off an antique mirror in a wrought iron frame and $150 off a pair of delicate, gold Victorian earrings. You'll likely have the most success at independent jewelry stores and electronics stores and flea markets.
Step 8: Schedule a Get Ready Day
The best way to avoid 67 trips to the post office, 7-Eleven, and CVS is a Get Ready Day. Purchase postage stamps, wrapping paper, tape, and ribbon; pick up prescriptions and cold remedies; stock up on pantry staples and refreshments. If you'll be mailing presents, either start collecting boxes now or split a bulk order with friends from the huge selection of decorative shipping materials found at USBox.com. "It's a good idea to use web sites that will wrap and ship for you," says Joe, "especially if you're traveling—you don't want to have to check bags. Make sure to send it out early and use UPS ground [to save money]."
Step 9: Remember the "Magic Factor"
Whether it's a Starbucks card or a cashmere sweater, the way it's packaged or wrapped counts. "Now, more than ever, it's about being smart and being creative," Jesse says. Put a small trinket in a big box with a beautiful bow, and it will be more fun to open up.
Joe and Jesse's other piece of advice is to think about what stresses out a friend or family member, and pick something that relieves that anxiety. Gift cards are useful and make great presents, but it's the magic factor that makes them special. "Our dad hates paying for practical things, so we buy him a gift card for the Gap," Jesse says. A forgetful friend who is always losing her keys may appreciate a decorative hook for the house.
Step 10. And if You're Still Scrambling...
Target, Nordstrom, and Zappos are three of more than 40 participants in the third annual "Free Shipping Day" on December 17. The complete list of stores is on FreeShippingDay.com
Missed the 17th? You may have to pay an overnight fee, but many sites will ship items within a few days of Christmas. Check USPS.com for mailing deadlines and DealHack.com/Deadlines for major retailers' purchase deadlines. Even Christmas morning is not too late to order from GiftCertificates.com, where you can print out or e-mail a personalized certificate redeemable at one of hundreds of companies, including Bed Bath and Beyond, Barnes & Noble, and Barneys New York.