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Bosses Day

Boss’s Day Cookie Gifts

Boss’s Day is October 16, 2025

This Boss’s Day, treat your bosses or supervisors to gifts like our unique cookies and treats. Our Bosses Day cookies are sure to bring a smile to your supervisor or manager!

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Buttercream-Frosted Thank You Sugar Cookies

Buttercream-Frosted Thank You Sugar Cookies

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Buttercream-Frosted Assorted Cupcakes - 12 cupcakes

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Buttercream-Frosted Assorted Cupcakes - 12 cupcakes

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Buttercream-Frosted Celebrate Cupcakes & Cookies

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Buttercream-Frosted Celebrate Cupcakes & Cookies

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You’re Incredible Party in a Box

You’re Incredible Party in a Box

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Thank You Traditions Gift Tower

Thank You Traditions Gift Tower

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Classic Gift Bundle with Message Tag - Enjoy

Classic Gift Bundle with Message Tag - Enjoy

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Thank You Treats Gift Pail

Thank You Treats Gift Pail

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Great Big Thank You Party in a Box

Great Big Thank You Party in a Box

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Thank You Cookie Gift Box

Thank You Cookie Gift Box

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Thank You Treats Gift Box

Thank You Treats Gift Box

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Thank You Cookie Card

Thank You Cookie Card

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Thank You Bakery Assortment - Medium

Thank You Bakery Assortment - Medium

available to ship september 15 2025

Thank You VIP Gift Tower

Thank You VIP Gift Tower

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Thank You 2-Pack Cookie Card

Thank You 2-Pack Cookie Card

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Best of Buttercream Cookie Box

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Best of Buttercream Cookie Box

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Cheryl’s Dessert Tray Gift Box - Grand - Thank You

Cheryl’s Dessert Tray Gift Box - Grand - Thank You

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Classic Bakery Gift Tower with Message Tag - Thank You

Classic Bakery Gift Tower with Message Tag - Thank You

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Thank You Cookie Gift Tin - Assorted Cookies

Thank You Cookie Gift Tin - Assorted Cookies

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Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription – 12 cookies

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You’re Incredible Cookie Card

You’re Incredible Cookie Card

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Cheryl’s Signature Bakery Sampler

Cheryl’s Signature Bakery Sampler

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Thank You Gift Bundle

Thank You Gift Bundle

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Thank You Gift Tower

Thank You Gift Tower

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Thanks For all You Do Cookie Card

Thanks For all You Do Cookie Card

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Thanks For All You Do Healthcare Party in a Box

Thanks For All You Do Healthcare Party in a Box

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Classic Gift Bundle with Message Tag - Thank You

Classic Gift Bundle with Message Tag - Thank You

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Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription - 24 cookies

Buttercream Frosted Cut-out Cookie of the Month - Pay-as-you-go Subscription - 24 cookies

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Flavor of the Month Cookie Club – Pre-pay

Flavor of the Month Cookie Club – Pre-pay

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Buttercream Frosted Cut-out Cookie of the Month Club - Pre-pay

Buttercream Frosted Cut-out Cookie of the Month Club - Pre-pay

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Sugar-Free Thank You Cookie Gift Box

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Sugar-Free Thank You Cookie Gift Box

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Gluten-Free Thank You Cookie Gift Box

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Gluten-Free Thank You Cookie Gift Box

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Vegan Thank You Cookie Gift Box

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Vegan Thank You Cookie Gift Box

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Enjoy Cookie Gift Box - 24 cookies

Enjoy Cookie Gift Box - 24 cookies

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Classic Assorted Cookies

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Classic Assorted Cookies

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Our Best of Buttercream Cookies

Our Best of Buttercream Cookies

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Cheryl’s Dessert Tray Gift Box - Large - Enjoy

Cheryl’s Dessert Tray Gift Box - Large - Enjoy

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Classic Cookie Assortment

FREE SHIPPING WITH CODE FRSHIP

Classic Cookie Assortment

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Best of Cheryl’s Dessert Tray - Large

Best of Cheryl’s Dessert Tray - Large

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Thanks a Latte Cookie Card

Thanks a Latte Cookie Card

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Cheryl’s Dessert Tray Gift Box - Large - Thank You

Cheryl’s Dessert Tray Gift Box - Large - Thank You

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Cheryl's Dessert Tray Gift Box - Medium - Thank You

Cheryl’s Dessert Tray Gift Box - Medium - Thank You

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Best of Cheryl’s Dessert Tray - Premier

Best of Cheryl’s Dessert Tray - Premier

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Thank You Cookie Gift Box - 12 cookies

Thank You Cookie Gift Box - 12 cookies

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Thank You Cookie Gift Box - 24 cookies

Thank You Cookie Gift Box - 24 cookies

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Classic Buttercream Frosted Cookies and Pretzels

Classic Buttercream Frosted Cookies and Pretzels

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Vanilla Buttercream-Frosted Sugar Cookie Flavor Box

Vanilla Buttercream-Frosted Sugar Cookie Flavor Box

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Best of Cheryl’s Dessert Tray - Medium

Best of Cheryl’s Dessert Tray - Medium

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Cheryl’s Sugar-Free Gift Tower with Message Tag - Enjoy

Cheryl’s Sugar-Free Gift Tower with Message Tag - Enjoy

available to ship january 05 2026

Enjoy Cookie Gift Box - 12 cookies

Enjoy Cookie Gift Box - 12 cookies

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Gluten-Free Cookie & Brownie Gift Box

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Gluten-Free Cookie & Brownie Gift Box

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Vegan Enjoy Cookie Gift Box

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Vegan Enjoy Cookie Gift Box

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Cheryl’s Dessert Tray Gift Box - Grand - Enjoy

Cheryl’s Dessert Tray Gift Box - Grand - Enjoy

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Tins With Pop® Best Boss Ever

Tins With Pop® Best Boss Ever

The Popcorn Factory

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Packed With Pop® Best Boss Ever

Packed With Pop® Best Boss Ever

The Popcorn Factory

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Cards With Pop® Best Boss Ever

Cards With Pop® Best Boss Ever

The Popcorn Factory

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Make You Smile 2 Gallon 3 Flavor Popcorn Tin

Make You Smile 2 Gallon 3 Flavor Popcorn Tin

The Popcorn Factory

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TPF Retro 3 Flavor Popcorn Tins

TPF Retro 3 Flavor Popcorn Tins

The Popcorn Factory

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Sweet Popcorn Sampler Box

Sweet Popcorn Sampler Box

The Popcorn Factory

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Make You Smile Gift Box

Make You Smile Gift Box

The Popcorn Factory

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18 Count Popcorn Variety Pack

18 Count Popcorn Variety Pack

The Popcorn Factory

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Snack Box

Snack Box

The Popcorn Factory

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Habanero Seasoned Popcorn Canister

Habanero Seasoned Popcorn Canister

The Popcorn Factory

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Strawberry Sparkling Wine Flavored Popcorn Canister

Strawberry Sparkling Wine Flavored Popcorn Canister

The Popcorn Factory

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Caramel Popcorn Canister

Caramel Popcorn Canister

The Popcorn Factory

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Teatime For One with Teapot Gift Basket

Teatime For One with Teapot Gift Basket

1-800-Baskets

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Classic Gourmet Gift Basket

Classic Gourmet Gift Basket

1-800-Baskets

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Majestic Grandeur Gourmet Basket

Majestic Grandeur Gourmet Basket

1-800-Baskets

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Premier Favorites Sweets & Treats Gift Basket

Premier Favorites Sweets & Treats Gift Basket

1-800-Baskets

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Distinctive Fruit Basket & Sweets Gift

Distinctive Fruit Basket & Sweets Gift

1-800-Baskets

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3 Count Oscar Mayer Bacon Cheddar Popcorn Bags

3 Count Oscar Mayer Bacon Cheddar Popcorn Bags

The Popcorn Factory

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3 Count Kraft Mac & Cheese Popcorn Bags

3 Count Kraft Mac & Cheese Popcorn Bags

The Popcorn Factory

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Godiva® Birthday Truffles Gift Box 12pc

Godiva® Birthday Truffles Gift Box 12pc

Simply Chocolate

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Godiva® Gold Ballotin Chocolates Box - 18 piece

Godiva® Gold Ballotin Chocolates Box - 18 piece

Simply Chocolate

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Godiva® Gold Ballotin Chocolates Box - 72 piece

Godiva® Gold Ballotin Chocolates Box - 72 piece

Simply Chocolate

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Godiva® Signature Truffles Box - 12 Piece

Godiva® Signature Truffles Box - 12 Piece

Simply Chocolate

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Godiva® Signature Truffles Box - 24 Piece

Godiva® Signature Truffles Box - 24 Piece

Simply Chocolate

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Thank You Gift Box

Thank You Gift Box

Wolferman's

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Deluxe Thank You Gift Box

Deluxe Thank You Gift Box

Wolferman's

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Bakery Favorites Tray

Bakery Favorites Tray

Wolferman's

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Grand Berry Breakfast Box

Grand Berry Breakfast Box

Wolferman's

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Delicious Mornings Gift Basket

Delicious Mornings Gift Basket

Wolferman's

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Mix & Match Thank You Bakery Gift - Pick 4

Mix & Match Thank You Bakery Gift - Pick 4

Wolferman's

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Mix & Match Thank You Bakery Gift - Pick 6

Mix & Match Thank You Bakery Gift - Pick 6

Wolferman's

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Mix & Match Thank You Bakery Gift - Pick 12

Mix & Match Thank You Bakery Gift - Pick 12

Wolferman's

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Deluxe "You Rock" Gift Basket

Deluxe “You Rock” Gift Basket

Harry & David

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You Rock Tower of Sweet Treats

You Rock Tower of Sweet Treats

Harry & David

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"Thank You" Meat and Cheese Gift Box

“Thank You” Meat and Cheese Gift Box

Harry & David

available to ship now

Thank You White Wine Gift Box

Thank You White Wine Gift Box

Harry & David

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Deluxe Tower of Chocolates® Gift

Deluxe Tower of Chocolates® Gift

Harry & David

available to ship now

Gourmet Brownie Assortment

Gourmet Brownie Assortment

Harry & David

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Deluxe Gourmet Gift Basket

Deluxe Gourmet Gift Basket

Harry & David

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"You Rock" Fruit and Sweets Gift Basket

“You Rock” Fruit and Sweets Gift Basket

Harry & David

available to ship now

Thank You Cookie Gift Basket

Thank You Cookie Gift Basket

Harry & David

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"So Very Thankful" Succulents

“So Very Thankful” Succulents

Harry & David

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Thank You Moose Munch® Premium Popcorn Tin

Thank You Moose Munch® Premium Popcorn Tin

Harry & David

available to ship now

Thank You Truffle Gift Box

Thank You Truffle Gift Box

Harry & David

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Floral Embrace™

Floral Embrace™

1-800-Flowers

Fields of Europe® for Fall

Fields of Europe® for Fall

1-800-Flowers

Harvest Glow™ Bouquet

Harvest Glow™ Bouquet

1-800-Flowers

Wonderful Wishes Bouquet™

Wonderful Wishes Bouquet™

1-800-Flowers

November Sun Lily Bouquet™

November Sun Lily Bouquet™

1-800-Flowers

Our Favorite Fall Tulips™

Our Favorite Fall Tulips™

1-800-Flowers

Happy Gerbera Daisies, 12-24 Stems

Happy Gerbera Daisies, 12-24 Stems

1-800-Flowers

Elegant Orchid

Elegant Orchid

1-800-Flowers

Money Tree

Money Tree

1-800-Flowers

Sweet Succulent Garden

Sweet Succulent Garden

1-800-Flowers

Personalized Message in a Bottle® Just Because

Personalized Message in a Bottle® Just Because

1-800-Flowers

Butterfly Snow Globe by CoolSnowGlobes

Butterfly Snow Globe by CoolSnowGlobes

1-800-Flowers

Happiness Blooms Shadow Box and Candle Gift Set

Happiness Blooms Shadow Box and Candle Gift Set

1-800-Flowers

Sweet & Delicious™

Sweet & Delicious™

Fruit Bouquets

Delightful Daisy Treat™

Delightful Daisy Treat™

Fruit Bouquets

Your Best Smile Bouquet®

Your Best Smile Bouquet®

Fruit Bouquets

Rainbow Delight ™ Bouquet

Rainbow Delight ™ Bouquet

Fruit Bouquets

Gourmet Drizzled Strawberries™

Gourmet Drizzled Strawberries™

Shari's Berries

Gourmet Dipped Fancy Strawberries

Gourmet Dipped Fancy Strawberries

Shari's Berries

Lavender Garden & Drizzled Strawberries

Lavender Garden & Drizzled Strawberries

Shari's Berries

Cherished Blooms & Drizzled Strawberries

Cherished Blooms & Drizzled Strawberries

Shari's Berries

Caramel Sea Salt Artisan Belgian Chocolate Berries

Caramel Sea Salt Artisan Belgian Chocolate Berries

Shari's Berries

Artisan Belgian Milk & Dark Chocolate Strawberries

Artisan Belgian Milk & Dark Chocolate Strawberries

Shari's Berries

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries

Signature Bundt Cake Assortment™ with Gourmet Drizzled Strawberries

Shari's Berries

The Office World's Best Boss Flower Bouquet

The Office World’s Best Boss Flower Bouquet

Created By: PrimeParty

The Office Golf Balls 12 Pack

The Office Golf Balls 12 Pack

Created By: GBM GOLF

Gift Box Fox Thank You

Gift Box Fox Thank You

Created By: Love and Luck Greetings

Inspiring Message Engraved Navigator Compass

Inspiring Message Engraved Navigator Compass

Personalization Mall

Executive Tan Leather Personalized Portfolio

Executive Tan Leather Personalized Portfolio

Personalization Mall

Initially Yours Personalized Fleece Blanket

Initially Yours Personalized Fleece Blanket

Personalization Mall

Signature Style Personalized Coffee Mug

Signature Style Personalized Coffee Mug

Personalization Mall

Black Stylus Personalized Ball-Point Pen

Black Stylus Personalized Ball-Point Pen

Personalization Mall

Signature Series Personalized Full Pad Portfolio

Signature Series Personalized Full Pad Portfolio

Personalization Mall

Thankful For Personalized Farmhouse Candle Jar

Thankful For Personalized Farmhouse Candle Jar

Personalization Mall

Professional Laurels Personalized LED Nameplate

Professional Laurels Personalized LED Nameplate

Personalization Mall

Professional Monogram Personalized Marble Desk Clock

Professional Monogram Personalized Marble Desk Clock

Personalization Mall

Personalized Sand-Filled Hourglass

Personalized Sand-Filled Hourglass

Personalization Mall

The Boss Engraved Marble Keepsake

The Boss Engraved Marble Keepsake

Personalization Mall

Best Boss Ever Personalized Printed Star Award

Best Boss Ever Personalized Printed Star Award

Personalization Mall

Lavish Last Name Engraved Bamboo Charging Valet Tray

Lavish Last Name Engraved Bamboo Charging Valet Tray

Personalization Mall

Namely Yours Personalized Men's Leatherette Writing Journal

Namely Yours Personalized Men’s Leatherette Writing Journal

Personalization Mall

Modern Initials Engraved Marble Name Plate

Modern Initials Engraved Marble Name Plate

Personalization Mall

Executive Personalized Alderwood Pen Set

Executive Personalized Alderwood Pen Set

Personalization Mall

Lucca & Sons™ Sausage & Cheese Gift Box

Lucca & Sons™ Sausage & Cheese Gift Box

1-800-Baskets

available to ship now

Deluxe Thank You Occasion Gift Basket

Deluxe Thank You Occasion Gift Basket

Harry & David

available to ship now

Grand Thank You Occasion Gift Basket

Grand Thank You Occasion Gift Basket

Harry & David

available to ship now

Supreme Thank You Occasion Gift Basket

Supreme Thank You Occasion Gift Basket

Harry & David

available to ship now

Engraved Black Small Book Clock and Keepsake

Engraved Black Small Book Clock and Keepsake

Things Remembered

Engraved Black Vegan Leather Padfolio and Pen Set

Engraved Black Vegan Leather Padfolio and Pen Set

Things Remembered

Engraved Bulova Ebony Crystal Recognition Clock

Engraved Bulova Ebony Crystal Recognition Clock

Things Remembered

Etched Corkcicle Square Cigar Glass

Etched Corkcicle Square Cigar Glass

Things Remembered

Engraved Waterford Lismore Essence Highball Pair

Engraved Waterford Lismore Essence Highball Pair

Things Remembered

Engraved Spinning Clock and Pen Stand

Engraved Spinning Clock and Pen Stand

Things Remembered

Engraved White Marble Card Holder

Engraved White Marble Card Holder

Things Remembered

Engraved Gloss Mahogany-Finish Gold Business Card Holder

Engraved Gloss Mahogany-Finish Gold Business Card Holder

Things Remembered

Engraved Professional Tan Leather Portfolio

Engraved Professional Tan Leather Portfolio

Things Remembered

Engraved Lenox Gold Monogram Bar Set

Engraved Lenox Gold Monogram Bar Set

Things Remembered

Etched Message Duet 8.5 oz. Stacking Decanter Set for Professionals

Etched Message Duet 8.5 oz. Stacking Decanter Set for Professionals

Things Remembered

Engraved Lenox "Tuscany" Monogram Cocktail Shaker Set

Engraved Lenox “Tuscany” Monogram Cocktail Shaker Set

Things Remembered

Engraved Black Hourglass Timer

Engraved Black Hourglass Timer

Things Remembered

Explore Wild Sampler - Thank You Gift

Explore Wild Sampler - Thank You Gift

Vital Choice

available to ship now

Wild Salmon Sampler - Thank You Gift

Wild Salmon Sampler - Thank You Gift

Vital Choice

available to ship now

MSC Wild Alaskan Sockeye Salmon - Thank You Gift

MSC Wild Alaskan Sockeye Salmon - Thank You Gift

Vital Choice

available to ship now

MSC Wild Alaskan Sockeye & Halibut Duo

MSC Wild Alaskan Sockeye & Halibut Duo

Vital Choice

available to ship now

MSC Wild Alaskan Halibut and Rainbow Carrots with Lemon Butter Sauce

MSC Wild Alaskan Halibut and Rainbow Carrots with Lemon Butter Sauce

Vital Choice

available to ship now

- Read Less

Boss's Day Gifts: The Perfect Way to Say Thank You

Looking for the perfect Boss's Day gift? You can't go wrong with a thoughtful gift from Cheryl's. Our specially curated selection of Boss's Day cookies and gifts is designed to show your gratitude and appreciation. From delicious cookie gift baskets to festive thank you cookies, we have the perfect gift to make your boss feel valued.

Celebrate Your Boss This October 16

This October 16, 2025, celebrate your supervisor with a gift they'll truly enjoy. Send a gift basket filled with sweet treats, and show them how much you appreciate their leadership and guidance. Choose from a variety of flavors, including our famous buttercream-frosted cut-out cookies, rich chocolate cookies, and more. Each gift is carefully packaged and ready to deliver a smile right to their office.

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