Step 1: Start Now
"Or yesterday!" says Joe. Jesse points out that a number of stores are having sales already. We discovered that many department stores and electronics stores have begun markdowns, and other companies, like Barnes & Noble, will take 5 percent off if you preorder. Check the cashback page at Bing to shop sales and find online coupons.
Step 2: Make a Gift List
Be a proactive shopper, not a reactive shopper. "Start a list of the people's names you have to buy for, and write down a gift idea or at least a store that represents them," Joe says. That way, when you do start shopping—online or at the mall—you'll be thinking of the person first, not the gift.
For inspiration, you can look to O editors' picks, find presents grouped by personality on Gifts.com, check your friends' wish lists on Amazon.com, or get the whole family on Giftag.com to easily make and share lists.
Step 3: Know Your Limits
Ask yourself, "What is my budget for the holidays?" Then break the total down by person. Financial expert Suze Orman recommends taking a serious look at your finances to come up with that number: How much is your mortgage or rent? Do you have credit card or student loan debt? If you figure out your monthly expenses and compare that with your income, you'll have a better idea of what you can afford this holiday season.
Another tip is to narrow your list to as few stores as possible, says Donna Smallin, author of The One-Minute Organizer Plain and Simple. "If I'm shopping online, I'll get toys in one place, because the shipping will cost less,” she says. "Also, if you charge all holiday purchases to one credit card, you'll have a convenient record of exactly how much you spent."
One often overlooked shopping expense is transportation. "Carpool with a friend or a relative, make a day of it," Jesse says. "It's better to have someone to bounce ideas off, and you'll get it done together. "
Step 4: Comparison Shop Like a Demon
"Go online and search for gift ideas before you hit the pavement," Jesse says. You'll get an idea of what's easier (and cheaper) to buy online and know what you can only get at a store. "The beauty of shopping early is being able to compare," says Jesse, who found a gift for a $100 less than the store next door. Try PriceGrabber.com, BizRate.com and DealHack.com to compare online.
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.