21 do's and don'ts of holiday shopping

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Holiday shopping shouldn’t be stressful, but it is for many of us.

Maybe you’re not 100% sure what to get the random coworker you drew for this year’s Secret Santa pool, or the aunt who is impossible to shop for. It happens. To help, we put together 21 foolproof picks for all the people in your life you’ve got a question mark next to.

We also put together some holiday gift do’s and dont’s to steer your shopping in the right direction.

Having trouble figuring out what to get people for the holidays? You can check out all of Insider Picks’ 2016 gift guides here.

Disclosure: This post is brought to you by Business Insider’s Insider Picks team. We aim to highlight products and services you might find interesting, and if you buy them, we get a small share of the revenue from the sale from our commerce partners, including Amazon. Jeff Bezos, CEO of Amazon, is an investor in Business Insider through his personal investment company Bezos Expeditions. We frequently receive products free of charge from manufacturers to test. This does not drive our decision as to whether or not a product is featured or recommended. We operate independently from our advertising sales team. We welcome your feedback.Have something you think we should know about? Email us at [email protected]

This article originally appeared at Insider Picks. Copyright 2016. Follow Insider Picks on Twitter.


Don't spend a ton of money on an unnecessary gadget.

Do give any technology-obsessed friend or family member the gift of extra battery life.

Anker PowerCore Slim 5000 Portable Charger, AUD$24.67 (US$17.99)


Don't buy underwear or lingerie for people who aren't your significant other.

Do shop for a cosy pair of flannel pajama pants instead. They're a safe bet, and something people don't always think to buy for themselves. We're also big fan of these unisex lounge pants from MeUndies.

J.Crew Men's Flannel Pajama Pant, $67.87
J.Crew Women's Gingham Flannel Pajama Pant, $67.87


Don't be afraid to replace (or upgrade) something you know they use every day.

Do be practical and consider their everyday needs. Things like slippers and dress socks get worn out over time, so you're doing them a favour by buying them a replacement before they'd eventually have to.

L.L.Bean Men's Wicked Good Moccasins, $94.61
L.L.Bean Women's Wicked Good Moccasins, $94.61


Don't buy fine jewellery unless you know the person's taste, or they have bookmarked something specific for you to shop.

Do be personal. A necklace with their initials on it is an easy, thoughtful gift.

Catbird Silver Heart Necklace, $134.37
Catbird Gold Heart Necklace, $296.17


Don't spend money on perfume or cologne unless you know their favourite scent.

Do get a scented candle. There's much less risk of someone hating it.

Le Feu de L'Eau Candle, $62


Don't buy bed sheets for someone unless you know the size of their mattress. (If you do know it, you can have a look at some of our favourite sheets here.)

Do get them a warm throw blanket to use when they're relaxing at home and watching Netflix this winter.

Pendleton Heritage Blanket, $327.70
Leesa Blanket, $204.30


Don't shy away from giving gift cards or money. Money is a very practical gift that people sometimes need more than presents.

Do get them a gift card to some place you know they like to shop.

Amazon.com Gift Card in a Snowflake Tin, from $34.28


Don't think too seasonal when you're gift shopping; red and green only look fun and festive for so long.

Do give gifts that can actually be used year round.

MVMT Hyde Sunglasses, $96


Don't buy tickets to a show unless you can talk specific dates with them beforehand.

Do give the gift of music on-the-go.

Braven 105 Portable Bluetooth Speaker, $68.49

Wine Awesomeness

Don't show up to a holiday party without a small gift for the host.

Do bring a bottle of wine or two with you.

Wine Awesomeness Variety Gift Box (3 Bottles), $61.70


Don't buy a big rolling suitcase for someone on a whim. People's preferences about luggage can be pretty specific, especially if they frequently travel for work.

Do get them a nice duffel bag they can use for weekend trips. Everyone should own at least one nice one.

Patagonia Arbor Duffel Bag 60L, $135.74
Everlane Premium Leather-Base Weekender, $178.25

Paper Source

Don't buy the first thing you see at Hallmark or Papyrus.

Do buy them a themed calendar that takes their interests into account. Just remember to get one for 2017, not 2016.

Cavallini Celestial Wall Calendar 2017, $30.10


Don't impose your book preferences on others, unless you know they share your love of science fiction or inspiring memoirs.

Do give them a cool coffee-table book to leaf through and display in their living room.

'Never Built New York' by Greg Goldin and Sam Lubell, $56.42


Don't get someone an art print unless you know their taste.

Do give them a gift card to Framebridge, so they can custom frame something they love -- be it a favourite photo or sports jersey -- exactly the way they want.

Framebridge Gift Card, from $34.28


Don't buy any hat that's not one-size-fits-all.

Do get them a warm beanie with character.

Topo Designs Pom Beanie, $24.68


Don't buy clothing for someone if you don't know their size.

Do look for a warm sweater. This is an exception to the no-clothing gift rule, since you can usually guess a size and be right, and it's something everyone needs in the winter.

Everlane Men's Cashmere Crew, $137.11
Everlane Women's Cashmere Crew, $137.11


Don't spend a ton of money on fancy leather gloves. Unless they're for someone who dresses up for work every day, they will go underappreciated.

Do think about people's needs for the winter. These texting-enabled gloves are incredibly convenient, especially for those who can never seem to detach from their phones.

The North Face Men's E-Tip Gloves, $61.70

The North Face Women's E-Tip Gloves, $61.70


Don't give people any giant decor items; they might not know what to do with them, or have the space for them.

Do pick up some small planters that will look great on your coworkers' desks.

Waen Mini Desk Planter, $61.70


Don't buy an expensive new work bag for someone unless they have told you what they like, or better yet, have an exact pick in mind. If you do, make sure you get a gift receipt -- just in case.

Do get them a wallet or small leather good instead. Wallets are items people usually forget to replace themselves.

Everlane Square Zip Wallet, $134.37
Bellroy Note Sleeve Wallet, $123.33

Yeti Coolers

Don't buy a silly mug as a gag gift that will sit in a kitchen cabinet and collect dust.

Do get them a top-of-the-line travel mug they will actually use.

Yeti Rambler 18 oz. Bottle, $39.65

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