Jen & Jessie’s 2020 Holiday Gift Guide

Putting together a holiday gift guide is one of my favorite posts to write every year.  It’s fun to find the items that make it easy to shop for the holidays.  After collaborating on our Gilt City Gift Guide, I decided to team up with my partner in crime, Jessie Bernhardt, to bring you the best gifts out there for 2020 with our gift guide!  It’s certainly been a strange year so showing your thoughtfulness no matter how you’re giving a gift is important this year.

For Her

2020 holiday gift guide

1. Alice & Wonder Chicago Forever & Ever ($59) // 2. Michelle Starbuck Designs Striped Hoop Earrings in Oxblood ($54) // 3. Sephora Laneige Dream & Wonder Gift Set ($29) // 4. Target Ember Mug ($99) // 5. True & Co Wireless Bra ($44) // 6. JCrew Factory Striped Knit Pajamas ($60) // 7. Revlon Pro One Step Hair Dryer & Volumizer ($39) // 8. share Tortoise Quarterfoil Studs ($24) // 9. Williams Sonoma SMEG Matte Black Toaster ($199) // 10. Nordstrom Pure Silk Pillowcase ($89) // 11. Anthropologies Suede Headband ($20) // 12. Equilibria Mint Balance Box ($110) [use jennaye for 15% off] // 13. The Sibyls 2020 Recovery Kit ($49) // 14. Alice & Wonder Tie Dye Pullover ($58) // 15. Nespresso Essenza Mini White ($149) // 16. Dudley Stephens Joggers ($138) // 17. Brooklinen Classic Core Sheets ($169) // 18. Lululemon All Yours Fleece Hoodie ($108) // 19. Spanx Drape Front Jacket ($178)

I am definitely buying Equilibria the season!  It’s been a gamechanger for me.  I also think their Mint Box is a really sweet gift so someone can try what they like.  It feels like something I’d love to get, but may not treat myself too.  Use the code ‘jennaye’ for 15% off.

I have been eyeing this Spanx jacket for YEARS!  Now that we’re ina comfy yet professional permanent state of mind, it made my Christmas list.  A silk pillowcase has also been on my list for years and years.  I hear that it is life-changing for your hair and really want to try it.

Is it 2020 or is it just me?  I really want a cute hoodie.  I usually rock old college hoodies or simple ones from Target, and now I’d love a cute one like this Lululemon hoodie.  This is my favorite headband from Anthropologie!  I wear it multiple times a week!  I bought this sweatshirt for my bestie for her birthday and reallllly want it for myself for Christmas!

For Him

2020 holiday gift guide

1. Allbirds Men’s Wool Runners ($95) // 2. Lululemon ABC Jogger Warpstreme Pants ($128) // 3. Sonos One from Amazon ($179) // 4. Airpods ($129) // 5. Solo Stove ($194) // 6. Bombas Men’s Snowflake Socks ($65) // 7. Shinola Monogrammed Notebook ($24) // 8. Crate & Barrel Brixton Rocks Glasses ($4.95 each) // 9. Bespoke Post Bitters Sampler Set ($30) // 10. LL Bean Men’s Wicked Good Moccasins ($79) // 11. Nordstrom Cotton Knit Lounge Joggers ($38) // 12. Nordstrom Mini Percussive Therapy Device ($199) // 13. Amazon Shiatsu Back & Neck Massager ($49) // 14. Nespresso Essenza Mini Black ($149) // 15. Crate & Barrel Clear Ice Molds ($35) // 16. Tushy Bidet ($79)

If you don’t have a Sonos One in your house, you should.  They are the BEST!  You can easily sync it to your phone and play multiple rooms at the same time.  A first or second pair of Airpods is also a winning move in my book.  They almost landed on multiple pages of our holiday gift guide.

For Clients

2020 holiday gift guide

1. Airpods ($129) // 2. Food 52 Pie Box ($28-$55) // 3. In Good Taste Wines Advent Calendar ($150) // 4. CB2 Voir Clear Glass Vase ($49) // 5. Blue Mercure Diptique Candle Set ($108) // 6. CB2 Hand Cut Decanter ($69) // 7. Williams Sonoma Bartesian ($349) // 8. CB2 Flkr ‘Fireplace’ ($99) // 9. Blondery Blondie/Brownie Box ($65) // 10. Pottery Barn Monogrammed Ice Bucket ($69) // 11. Usual Wine Reserve Wine Box of 6 ($120) // 12. Anecdote Italian Fig Candle ($38) // 13. Carol’s Cookies Cookie Box ($38)

With all of the Zoom calls we’re on, Airpods are always a thoughtful gift. If you’re a cocktail fan, Bartesian is supposed to be SUPER fun!  Plus, you can honestly never go wrong with Diptique.  For a more unique approach, I’d check out Anecdote.  They’re a newer shop in Hinsdale with beautiful artwork, furniture, and candles!

For Boomers

2020 holiday gift guide

1. Merrell Slippers ($90) // 2. Lifetherapy Gift Set ($39) // 3. Amazon Travel Cigar Humidor ($22) // 4. Dyson Cordless Vaccuum ($349) // 5. Anthropologie USB Candle Lighter ($30) // 6. Anthropologie Glass Cloche ($44) // 7. All Birds Sneakers ($95) // 8. Facebook Portal ($279) // 9. West Elm Stainless Steel Watering Can ($75) // 10. Tushy Bidet ($79) // 11. Crate & Barrel Bistro Mug ($14) // 12. Athleta Sherpa Jacket ($125) // 13. Kindle ($89) // 14. Target Electric Kettle with Temperature Control ($99) // 15. Anthropologie Monogram Water Bottle ($20)

My mom is the biggest Merrell’s fan, and if she plays her cards right, these will be waiting under the tree for her.   I absolutely love these bistro mugs, and if your parents need an upgrade, grab them!

A good pair of sneakers like these Allbirds are the perfect gift for parents!  Giving people gifts to stay active is always a good idea. This Sherpa Jacket is so cute for the stylish mom!  If you’re not going for Merrell’s, I highly recommend the Sorel’s.  A Kindle is always a good idea for parents!

For Kids

jen and jessies holiday 2020 gift guide for kids

1. Kid’s Wooden Playhouse // 2. Wonder Women Go Fish (Buy & Support Local!) // 3. Little Tikes Trampoline // 4. Melissa & Doug Pots & Pans // 5. Magnatiles // 6. My First Book of Patterns // 7. Mid Century Modern Tables & Chairs // 8. Kids Activity Yoga Mat // 9. Kids Charcuterie Board // 10. The Little Dreamer Book // 11. Melissa & Doug Scoop & Serve Ice Cream // 12. Ikea Kitchen Set // 13. Bristle Blocks // 14. Toddler Stand // 15. Brainquest // 16. Clover Kids Oh Joy! Pajamas

It’s hard not to go overboard with kids.  They’re so fun to shop for!  Jessie and I really love toys that are fun but cue learning or pretend play.  I am all about the Kids Activity Yoga Mat.  I think I actually want to start doing yoga with Emmie.  We already have the Ikea Kitchen and Emmie uses it EVERYDAY!  It’s such a great gift.  I’d like to get the charcuterie board to go with it.  Two of the other favorites in our home are Magnatiles & the Melissa & Doug Ice Cream Set.

The Entertainer

entertaining gift ideas jen and jessies 2020 holiday gift guide

1. Our Place Always Pan // 2. Café Appliances Coffee Maker // 3. Juliet Optic Red Wine Glass // 4. Half Baked Harvest Cookbook // 5. Great Jones Fully Baked Baking Set // 6. Make It A Double Jigger // 7. Grl Walks Into A Bar Set // 8. Electric Wine Aerator // 9. 36″ Cheese Board // 10. Meal Planner // 11. Sous Vide // 12. Pasta Sampler Pack // 13. Electric Milk Frother // 14. Agate Coasters // 15. Composite Agate Cheese // 16. Odor Absorbing Screen

The entertainer gift guide is always my favorite.  I love everything in here.  It’s so hard for me to pick a favorite, but I think it’d be the Our Place Always Pan.  Then, it’s a toss-up between the Fully Baked Set and the Coffee Maker.  You honestly can’t go wrong here!

Local Chicago

local chicago gift guide

1. Bitter Pops Advent Calendar // 2. Adore Table Flower Weekly Delivery // 3. Four-sided Chill Pill Ornament // 4. Carol’s Cookies Cookie Box // 5. Club Lucky Martini Kit // 6. All Star Press Fly the “W” Pin // 7. The Fig Tree Date Night In // 8. All Star Press Chicago Bookshelf Print // 9. XO Marshmalloow Brookie Dough OMG // 10. Bon Aprontit Blueberry Apron // 11. Alice & Wonder Chi City Sweatshirt // 12. Building Blocks El Train Toy // 13. Building Blocks Ideal Snow Shovel // 14. Flowers by Stem Weekly Floral Delivery // 15. Timeless Toys Race to the Finish // 16. P.O.S.H. Les Parisiennes 

Have you seen our Gilt City Holiday Gift Guide yet?  Click here! 

This year, it’s even more important than ever to shop small, which is why we rounded up our favorites.  A huge thanks to our Instagram followers because many of the ideas came from you!  I currently subscribe to Adore Table Flower Weekly Delivery and I love it.  I also have the Alice & Wonder Chi City Sweatshirt on my list!  Dying for that one!!

Under $50

under 50-dollar gift ideas-2020 holiday gift guide

1. SnackRiot Monthly Snack Subscription // 2. Framebridge Framed Instagram Photo // 3. Olive & June Studio Box // 4. Nordstrom Luv Scrub // 5. Nordstrom Silk Hair Ties // 6. CB2 Curve Ball Match Striker // 7. CB2 Clear Jewerly Holder // 8. share 2021 Not Soon Enough Candle // 9. share The Gold Essentials // 10. share 100 Cookies Cookbook // 11. Bamboo Squatty Potty from Amazon // 12. Pom Pom Fur Hat from Amazon // 13. Alice & Wonder CHI Hat // 14. Anthropologie WYP Terrazzo Porter Travel Mug // 15. Anthropologie Gisele Coasters // 16. JCrew Blue Light Glasses 

Gift exchanges may look a little different this year, but that doesn’t mean you can’t give thoughtful gifts!  I love so many of these ideas, but in particular the share 100 cookies cookbook and Olive & June Studio box.

Stocking Stuffers

stocking stuffer ideas - 2020 holiday gift guide

1. Allbirds Socks // 2. Water Bottle // 3. Lululemon Gloves // 4. RBG Stationery Set // 5. share Chenille Slipper Socks // 6. Alice & Wonder Not Today Mug // 7. Anthropologie Cable Knit Mittens // 8. All She Wrote Scratch-Off Map // 9. Anthropologie Monogram Mug // 10. QUAY All Nighter Blue Light Glass // 11. XO Marshmallow Dat Cone Dough Marshmallow // 12. Lululemon Every Ready Crossbody // 13. JOBY Gorilla POD Stand // 14. Chic Moda Exercise Sliders // 15. Dermstore Microneedle Face Roller // 16. JCrew Plaid Masks 3-Pack

How cute are these stocking stuffers?  I think the RBG Stationery Set will fly off the shelves.  I am also dying for the share Chenille Slipper Socks.  We bought these for my mother-in-law for her birthday and she loves them.  They’re on my list, too! I hope you love this holiday gift guide as much as I do!  Here are a few other posts you may like:

Meet Jen

I’ve always had a love affair with creation. Since I was a child, I handmade my gifts or combined toys to design something new. Fast forward twenty years, and I’m still making my gifts every holiday and designing new ways to do things.


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Where I Shop


In order to grow my small business, I earn revenue in a few different ways. I publish sponsored posts from time to time, which are always labeled. Sometimes I earn an affiliate commission on the sales of products or business resources I link to. I only feature items I genuinely love and want to share. Thank you for reading and supporting my small business!

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