This Valentine’s Day, show the entrepreneur in your life how much you appreciate their hustle and heart with a thoughtful gift tailored to their busy lifestyle. Entrepreneurs often juggle endless to-do lists, late nights, and big dreams, so finding a gift that brings them joy can make all the difference. Whether it’s something to help streamline their workday, elevate their confidence, or encourage well-deserved indulgence, the right gift can show how much you care about their success and well-being. From fashions they’ll love to cozy essentials and stylish home office upgrades, this 2025 gift guide is filled with thoughtful Valentine’s Day gifts to make them smile.
Clif Family Winery & Farm Eat Chocolate, Drink Wine
Clif Family Winery & Farm’s thoughtfully curated gift sets offer exceptional wines with artisan treats, making them the perfect Valentine’s Day gift for the busy entrepreneur who deserves a moment to unwind. This winery is a testament to sustainable farming, growing organic fruits, vegetables, and nine grape varietals across 90 acres of CCOF-certified vineyards.
Clif Family Winery & Farm’s Eat Chocolate, Drink Wine set features the Clif Family Winery & Farm’s 2021 Kit’s Killer Cab Napa Valley Estate Cabernet Sauvignon, a silky, organically farmed wine that pairs perfectly with chocolate. Your special entrepreneur will enjoy a trio of TCHO chocolates designed to elevate the tasting experience. From the exclusive Napa Noir bar, crafted with cacao nibs aged in wine barrels, to the rich Dark Duo and the irresistible Toffee Crunch, this set is a luxurious celebration of bold flavors and artisan craftsmanship. Retails for $100 at cliffamily.com.
Simone I. Smith Sweetheart Hoops – Large
A pair of heart-shaped hoops from Simone I. Smith is a meaningful Valentine’s Day gift, blending elegant design with the brand’s empowering story of resilience and strength. Founded by Simone I. Smith, a jewelry designer and cancer survivor, the brand creates stunning pieces that celebrate love, individuality, and giving back. The Sweetheart Hoops by Simone I. Smith, crafted in 18K yellow gold over sterling silver with a diamond-cut heart shape, are a stunning blend of sophistication and charm. Their large, bold design makes a statement while maintaining a timeless style, perfect for elevating any outfit.
For entrepreneurs, Simone I. Smith’s Sweetheart Hoops’ versatility effortlessly transition from professional meetings to evening events. Whether paired with a power suit or a chic cocktail dress, the Sweetheart Hoops are a must-have accessory that reflects both style and ambition. Retails for $199 at simoneismith.com.
Just Shoes For Kids – Igor Women’s Chloe MC Boots
Just Shoes for Kids began from a mother’s determination to make finding stylish, high-quality footwear for children stress-free. Offering top European designs, free shipping for the perfect fit, and quick, friendly customer support, this online store ensures convenience and style for busy parentpreneurs. Plus, with each purchase 1% of net profits go to the ELIJA Foundation, supporting Autism outreach—a heartfelt mission inspired by the founder’s own journey as a mom to two Autistic boys.
In addition to children’s shoes, Just Shoes For Kids offers styles for moms too. The Igor Women’s Chloe MC Boots combines sleek style and practical functionality, making them the perfect choice for rainy days. Designed in Spain, these monochrome track-style rain boots feature a chic matte finish, textile accents, and a removable comfort insole for all-day ease. They also feature vertical grooves on the sole for added support, ensuring entrepreneurs stay fashionable no matter the weather. Retails for $92 at justshoesforkids.com.
DUER Men’s No Sweat Straight and Taper Pants
DUER is all about creating versatile clothing that offers comfort, style, and functionality, making their pants a perfect Valentine’s Day gift for busy entrepreneurs. DUER’s Men’s No Sweat Dress Sweatpants are the perfect combination of a polished, professional look and the cozy feel of sweatpants. Designed with DUER’s innovative No Sweat fabric, these pants are breathable, moisture-wicking, and flexible, ensuring all-day comfort whether your Valentine is powering through meetings or running errands. Because of their sleek, straight-leg silhouette, they effortlessly transition from work to after-hours, making them an ideal addition to any entrepreneur’s wardrobe.
Crafted with the needs of on-the-go professionals in mind, DUER’s No Sweat Dress Sweatpants feature hidden zippered pockets for essentials, a finish that pairs well with any outfit, and durable construction that lasts. These pants come in a variety of colors and size variations to fit your Valentine’s needs. Retails for $129 at shop.duer.com.
Sol Rouge Petit Sirah 2018
Sol Rouge Petit Sirah 2018 is a luscious red wine born from a dream to create something extraordinary. Founded by Jill and Bryan in 2004, Sol Rouge is nestled in the rugged beauty of Lake County’s Red Hills in Northern California. Their journey began with discovering a 70-acre walnut orchard on the slopes of Mt. Konocti, a dormant volcano offering ideal conditions for cultivating world-class wines. By 2006, they planted their vineyard with nine varietals and twenty clones, leveraging the volcanic soil and high elevation to craft wines of exceptional character. The result is a winery rooted in passion and the unique terroir of this mountainous region
On the nose, Sol Rouge Petit Sirah 2018 unveils aromas of ripe blueberries, blackberries, tobacco, dark chocolate, and a hint of mineral essence. The palate reveals the intensity of the volcanic region, offering rich flavors and velvety spiciness that culminate in a long, satisfying finish. Sharing a bottle of this award-winning wine creates a memorable experience, whether enjoyed over a candlelit dinner or with decadent chocolates. Retails for $90 at solrouge.com.
GoWith Socks
Socks from GoWith Socks make a thoughtful Valentine’s Day gift for entrepreneurs, offering them a stylish daily reminder to step into each day with confidence and care. GoWith socks combines over 30 years of expertise with premium materials like cotton, merino wool, and bamboo to deliver comfortable and durable socks. Designed in Germany and made in Turkey, these high-quality socks cater to every lifestyle, from hikers and runners to those prioritizing foot health with compression or diabetic-friendly options. With a 4.7 Google seller rating and a growing presence in the U.S. market, GoWith is a trusted choice for stylish, functional socks that go the distance. Whether your special someone would enjoy pure cotton socks, Alpaca hiking socks, or Vintage Nordic socks, there is something for every person on your list this Valentine’s Day at gowithsocks.com.
Teva Women’s Grandview GORE-TEX Hiking Boot
If your special entrepreneur loves to go on outdoor adventures in their time off, gifting footwear that inspires exploration is a perfect gift. Teva has been fueling adventures since 1984, when the original sport sandal was created by a resourceful river guide at the Grand Canyon. Today, Teva continues to innovate with eco-friendly materials, like recycled plastic and supports outdoor conservation efforts.
Inspire all her adventures with Teva’s Grandview GORE-TEX Hiking Boots, designed for both day hikes and extended excursions. These hiking boots offer wearers the rugged dependability and comfort they seek when they’re on the trail. Made with waterproof leather, quick-dry mesh, and a GORE-TEX bootie, these shoes keep feet dry and protected from the elements. A wider toe-box provides freedom for the toes, while an adjustable Universal Heel Lock System minimizes pressure during downhill treks. With a Vibram™ Megagrip outsole for superior traction on wet and dry surfaces, and a cushioned, supportive footbed, these shoes are perfect for tackling any trail. Plus, they’re eco-friendly with recycled materials and sustainable leather. Retails for $175 at teva.com.
Sierra Madre Ready Skort and Mock Tee Shirt
Sierra Madre is redefining women’s golf apparel with sleek, technical designs made for confidence on and off the course. The brand ensures women can enjoy edgy and functional alternatives to traditional golf wear. Their versatile and stylish apparel makes an empowering Valentine’s Day gift for entrepreneurs, encouraging drive and confidence in their busy days.
Sierra Madre’s Golf Skort is designed for women who are always on the move. With its sleek design, built-in shorts for comfort, and versatile look, it transitions seamlessly from the golf course to meetings or errands. This skort is an ideal Valentine’s Day gift for entrepreneurs, offering a practical yet stylish wardrobe staple to keep them feeling ready for anything. Retails for $78 at sierramadregolf.com.
Complete the look with Sierra Madre’s The Mock Neck Tee, a thoughtful Valentine’s Day gift for entrepreneurs who value versatility and sophistication in their wardrobe. This tee is made from 100% Peruvian cotton and is naturally breathable. It features a flattering mock neckline that sits comfortably, raglan sleeves for easy movement, and a modern boxy fit. Retails for $48 at sierramadregolf.com.
Gina DeSantis Ceramics Large Luna Noodle Bowl
Gina DeSantis Ceramics, founded in 2013, brings beautifully handcrafted pottery to life from an old automobile factory in Lakewood, Ohio. With over two decades of experience in clay, Gina designs and hand-throws each piece, supported by her skilled team for tasks like trimming, glazing, and firing. Her work has been featured in Uncommon Goods, Anthropologie, and the Sundance catalog, and is available in over 400 retailers nationwide. All pieces are proudly made in the USA.
Gina DeSantis’s Large Luna Noodle Bowl is a beautifully designed pasta bowl, perfect for enjoying hearty meals. This beautiful bowl makes a thoughtful Valentine’s gift for entrepreneurs, making mealtime a relaxing break from their busy schedules. It features a tall shape and convenient nooks for resting chopsticks (not included). At 3.5 inches tall and 7.5 inches wide, it’s ideal for soups, noodles, and pasta dishes. It is microwave and dishwasher safe. Retails for $70 at ginadesantisceramics.com.
Sound+Sleep SE
LectroFan’s Sound+Sleep SE is an ideal tool for entrepreneurs looking to optimize their rest and recharge for peak performance. Entrepreneurs often face high levels of stress and busy schedules, making quality rest essential for maintaining focus and productivity. With 64 high-definition, non-looping sound profiles crafted from real-world recordings, this advanced sound machine creates a soothing, immersive environment to promote deeper sleep and relaxation. The Sound+Sleep SE’s patented Adaptive Sound technology intelligently adjusts to your environment, masking distractions and ensuring uninterrupted sleep, so you can wake up refreshed and ready to tackle your goals.
Beyond better sleep, the Sound+Sleep SE can help entrepreneurs find moments of calm during the day. Whether used for relaxation during a hectic workday or a focused meditation session, the machine’s realistic, evolving soundscapes create a serene atmosphere wherever needed. Its sleek design and user-friendly features make it a seamless addition to any workspace or home office. Retails for $129.95 at lectrofan.com.
Extract Labs THCV Capsules and Organic CBD Oil
Extract Labs is driven by a mission to make premium hemp products accessible to everyone. Founded by veteran Craig Henderson, who discovered hemp’s therapeutic benefits firsthand, the company has grown from a garage project into an industry leader. They’re committed to innovation, exceptional customer service, and community support through discount programs. Additionally, Extract Labs is dedicated to exploring the potential of minor cannabinoids and creating affordable, effective products that make a difference in any entrepreneur’s life.
Extract Labs’ THCV Capsules combine the power of THCV and CBG to help entrepreneurs stay focused, energized, and in control of cravings. Each capsule contains 5mg of THCV and 15mg of CBG, designed to boost energy, enhance focus, and support appetite management naturally. These capsules are made with organic American-grown hemp, full-spectrum hemp oil, and organic fractionated coconut oil. They’re crafted for maximum potency and absorption, helping to keep the focus on where it needs to be. the THCV Capsules come with 60 capsules per bottle, certified organic ingredients, and third-party lab testing for peace of mind. Retails for $89.99 at extractlabs.com.
Complete your Valentine’s gift with Extract Labs’ Organic CBD Oil | Daily Support, a fan-favorite full-spectrum formula designed to provide potent, daily wellness support. Packed with CBD and minor cannabinoids, this USDA-certified organic oil utilizes the “entourage effect” for enhanced benefits while maintaining less than 0.3% THC. It is available in four strengths and features a natural hemp flavor. Entrepreneurs will love using this daily to promote focus, reduce stress, and feel balanced amidst their demanding schedules.
Cozy Earth Bamboo Hoodie and Bamboo Jogger Pant
Cozy Earth creates products that elevate everyday life with unmatched quality, timeless style, and thoughtful design. They take pride in responsibly sourcing materials and partnering with ethical manufacturers to craft luxuriously soft and durable essentials for the home and wardrobe. Cozy Earth’s Bamboo Hoodie makes the perfect Valentine’s Day gift for someone you love—or even yourself! This softer-than-soft women’s hoodie wraps her up in a cocoon of comfort as it is crafted from breathable bamboo viscose. Its relaxed fit, drawcord, sleeve cuffs, and elegant embroidered details make it as stylish as it is cozy. The hoodie’s enhanced weave ensures long-lasting quality and prevents pilling, making it a gift that keeps giving. Retails for $155 at cozyearth.com.
shortyLOVE amuse – medium crossbody bag
shortyLOVE is a thoughtfully designed athleisure handbag line created by Sloane Gibney Grossberg to offer style, comfort, and practicality for today’s active women. Fully woman-owned and operated, the brand grows organically to stay true to its mission of empowering women with bags that work as hard as they do, blending timeless sophistication with unmatched convenience. The shortyLOVE amuse – medium crossbody bag is the perfect everyday companion for your Valentine. Designed to be “just right” in size, it measures 10″ x 11″ x 2.25″, making it ideal for daily errands or special outings. She can wear it as a crossbody, or shoulder bag, or carry it by the handle, adapting to any occasion.
shortyLOVE’s amuse – medium crossbody bag exterior features a convenient front zip pocket to keep essentials like her phone, keys, and lip balm within easy reach. Crafted from durable, water-resistant nylon twill inspired by high-end Italian fabrics, this bag offers a soft, feminine aesthetic with everyday practicality. As a Valentine’s Day gift, this bag is a thoughtful way to show your love with something stylish, functional, and built to last. Retails for $158 at shortylove.com.
Omaha Steaks Date Night Box + FREE Dessert
Omaha Steaks, a family-owned company since 1917, has earned a reputation as one of the world’s most esteemed meat purveyors. From its humble beginnings as a butcher shop in Omaha, Nebraska, the company has grown into an international brand, known for delivering premium quality meat and gourmet foods. Whether it’s their USDA Certified Tender filet mignons or their signature gourmet sides, Omaha Steaks always guarantees an exceptional dining experience.
This Valentine’s Day, Omaha Steaks’ Lover’s Box offers the perfect way to celebrate love with a luxurious, restaurant-quality meal at home. The centerpiece of the box is the Butcher’s Cut Filet Mignons, expertly aged for 30 days and double-trimmed for a lean, fork-tender bite. These beautiful steaks pair with buttery green beans, crispy hash browns, and fragrant garlic baguettes. To sweeten the evening, the box includes Caramel Apple Tartlets for a delectable dessert. This box is a thoughtful and indulgent gift that embodies Omaha Steaks’ dedication to quality, ensuring your Valentine’s dinner is unforgettable. Retails for $119.47 at omahasteaks.com.
Blenders Meister X2 Prime 21 and Heart Rush Sunglasses
Blenders Eyewear sunglasses make perfect Valentine’s Day gifts for him and her, offering bold, stylish designs and UV protection, ensuring your loved one sees the world through a lens of style and adventure. Their vibrant, bold designs are inspired by the laid-back, beachy vibe of San Diego.
Blenders’ Heart Rush Sunglasses combine classic round frames with modern upgrades, making them a thoughtful and stylish Valentine’s Day gift for her. With a chic matte tortoise and peach frame and customizable lens options like blue light, polarized, or high-index upgrades, these glasses are a great match for anyone. Their scratch-resistant lenses and 100% UV protection ensure lasting quality, while color options like champagne, pink, or blue mirrored lenses let her showcase her personal style. She’ll love that they’re perfect for work, play, or relaxation. Retails for $89 at blenderseyewear.com.
Blenders’ PRIME 21 – Color Block Sunglasses are a bold and stylish Valentine’s Day gift for him, blending standout design with top-tier performance. Featuring polarized PureBlend™ lenses for superior clarity and scratch resistance, these special-edition shades were designed in collaboration with Deion Sanders and showcase exclusive details like the PRIME 21 logo and “IT’S PERSONAL” engraved on the brow. The striking color-blocked black and white frame, accented with metallic gold, pays homage to Coach Prime and Colorado fans, making these sunglasses a statement piece he’ll love to wear. Packaged in premium case and packaging, so they are ready to gift this Valentine’s Day. Retails for $89 at blenderseyewear.com.
Johnnie-O Jimmy Stretch Knit Flannel Lodge Shirt
This Valentine’s Day, gift the perfect blend of style and comfort with Johnnie-O’s Jimmy Stretch Knit Flannel Lodge Shirt, a standout from their Top Shelf collection. Inspired by the brand’s unique fusion of East Coast tradition and West Coast casual, this flannel shirt is designed for modern comfort and timeless appeal, perfect for the home office. Made from an ultra-soft stretch cotton flannel blend, it combines the classic look of an overshirt with the warmth and weight of a work jacket. Thoughtful details like a spread collar, two button-through chest pockets, and a signature JO label add a refined touch, making it a versatile piece for any occasion.
Whether your Valentine is heading out for a brisk walk, working from home, on a zoom call, or dressing up for a casual date night, the Lodge Shirt offers exceptional comfort and style. Its stretch fabric blend provides easy movement and a perfect fit, while its cozy feel is ideal for the cooler season. On sale for $99 at johnnie-o.com.
Kyte Baby Women’s Cross Front Bralette and Midi Brief
Kyte Baby is well-known for its buttery-soft apparel for babies, but did you know it also makes some goodies for grown-ups? Kyte Baby Bralettes are made from silky soft bamboo lyocell that’s gentle on sensitive skin. Its wireless design offers all-day and all-night comfort, while the crossover front allows for easy nursing access for post-partum mompreneurs. With adjustable straps for a customized fit, this bralette is a thoughtful gift for moms seeking effortless style and functionality, especially for the work-from-home life. The bralettes come in a variety of neutral shades to compliment the skin. Retails for $48 at kytebaby.com.
Complete her gift with Kyte Baby Midi Briefs, which are made from the same soft, stretchy bamboo fabric that feels light and breathable all day long. Designed with a flattering midi cut, these full-coverage undies provide a barely-there feel while keeping entrepreneurs confident and comfortable as they run their businesses.
WLIVE Modern Minimalist LED TV Stand for 65 Inch TV
WLIVE’s innovative and functional home furnishings, like their Sideboards, Lift-Top Coffee Tables, and Side Tables, make working remotely a breeze. As one of Amazon’s top furniture brands, trusted by over 1.5 million households, WLIVE helps entrepreneurs create organized and inspiring spaces that reflect their refined taste. Perfect for staying productive and polished, their products are a smart choice for modern professionals.
The WLIVE Modern Minimalist LED TV Stand for 65 Inch TV makes an ideal Valentine’s Day gift for entrepreneurs who value efficiency and modern design. Its sleek lines and dynamic LED lighting, with 20 vibrant colors, create a customizable ambiance for movie nights or late-night work sessions. Designed to support TVs up to 65 inches, this stand provides a secure, stylish base for entertainment or productivity, making it a thoughtful addition to any living or workspace. The hidden storage compartments and open drawer offer ample space to organize media essentials or work-related items, ensuring a clutter-free environment that promotes focus and relaxation. Additionally the built-in cable management keeps cords tidy, creating a polished and professional look. Retails for $129.99 at wlivehome.com.
Jermann, The R 2022
The Jermann estate was founded in the Collio Goriziano (the eastern hillsides) of Friuli in 1881 when Anton Jermann emigrated from Austria. Until the 1970’s the Jermann family farmed livestock and grains in addition to tending grapevines for bulk sale. The modern winery was launched in earnest in 1975 with the release of Vintage Tunina by Silvio Jermann, the fifth generation in Friuli, who brought clean winemaking practices to the estate.
Jermann’s Pinot Grigio is a vibrant expression of Friuli’s winemaking heritage, crafted from a small, organically grown estate vineyard. The wine undergoes maceration on the skins for enhanced color and texture, followed by six months of lees aging in stainless steel. It offers enticing aromas of nectarines, crushed stones, and herbs, while the palate delivers a textured, medium- to full-bodied experience with zesty flavors, crisp minerality, and a bone-dry finish. Retails for $39.99 at vivino.com.
Bloomers Intimates Pantyloon® Slip Shorts
For entrepreneurs who need to stay comfortable while juggling busy schedules, Bloomers Intimates Pantyloon® Slip Shorts are a game-changer wardrobe staple. Whether your Valentine is presenting at a meeting or rushing between tasks, the Pantyloon® offers a seamless, chafe-free fit that keeps her feeling secure and confident in her dresses and skirts.
Bloomers Intimates’ Pantyloon® Slip Shorts come in romantic Queen’s Lace and spicy Cougar Lace and are designed with full thigh coverage to prevent chafing. She’ll love these shorts smooth curves without any constriction, making them ideal for all-day wear. The scalloped lace edge stays invisible under clothes, while the 4-way stretch ensures maximum comfort and flexibility. With a 100% cotton gusset, they’re as breathable as they are beautiful, making them a staple for anyone seeking confidence. Pantyloon® comes in many colors to choose from. Retails for $45 at bloomersintimates.com.
Old World Christmas Santa’s Magic Castle Ornament
A Christmas ornament from Old World Christmas is a unique and sentimental gift for Christmas ornament lovers that keeps your bond shining year-round. Since 1979, Old World Christmas has been crafting exquisite ornaments with traditional techniques that celebrate cherished memories and bring magic to every holiday season. They have a variety of Valentine’s Day-themed ornaments any holiday enthusiast would love. Old World Christmas’s Santa’s Magic Castle Ornament is a pink, whimsical holiday treasure that comes from their Wooden Cottages collection. This hand-assembled wooden treasure lights up a tree while revealing delightful hidden surprises like a gingerbread man, a Christmas pickle, and Santa himself. Retails for $29.99 at oldworldchristmas.com.
CamelBak Chute® Mag 25 oz Water Bottle, Insulated Stainless Steel
CamelBak designs its products for durability, convenience, and hydration on the go, making them perfect for any entrepreneur’s daily routine. The CamelBak Chute Mag 25 oz Insulated Stainless Steel Water Bottle is the ideal Valentine’s Day gift for the entrepreneur in your life. Designed to keep drinks cold for hours, this durable bottle ensures they stay hydrated during long meetings, busy workdays, or on-the-go adventures. The magnetic cap stows securely while drinking, making it hassle-free to use, while its sleek stainless steel design adds a touch of style. It features a leak-proof construction and offers easy portability, so it can be brought anywhere the day takes your Valentine. Comes in many colors. Retails for $30 at camelbak.com.
Girlan Pinot Grigio Alto Adige DOC 2023
The Girlan Pinot Grigio Alto Adige DOC 2023 is a vibrant Alpine white wine crafted in celebration of Cantina Girlan’s 100th anniversary. Sourced from the foothills of the Dolomites, this 100% Pinot Grigio thrives in the region’s unique glacial and volcanic soils at elevations of 400-500 meters. With notes of mountain herbs, crisp apples, and ripe pears, this wine offers a lively palate and a charming nose. Hand-harvested and aged on the lees for six months in stainless steel, it reflects Alto Adige winemaking’s authentic terroir and meticulous craftsmanship. Retails for $22.99 at girlan.it.
Tenuta Regaleali, Lamùri Nero D’Avola Sicilia DOC 2019
Celebrate San Valentine with Tenuta Regaleali’s Lamùri Nero D’Avola, a luscious and heartfelt wine from Sicily, one of the Mediterranean’s crown jewels for breathtaking landscapes and exceptional flavors. Named after the Sicilian word for “love,” this wine reflects the deep devotion of the Tasca d’Almerita family, who have upheld the island’s winemaking traditions for centuries. Made from Nero d’Avola grapes grown in the high-altitude vineyards of Tenuta Regaleali, it offers vibrant aromas, a balance of freshness, and velvety tannins achieved through careful aging in a blend of barriques. This wine is a perfect pairing for love-filled moments and memories. Retails for $20 at tascadalmerita.it.
Buffy Cloud Comforter
Buffy redefines bedding with sustainability at its core, crafting comforters and pillows filled with recycled plastic bottles and using eucalyptus fibers and botanical dyes for its soft, eco-friendly shells. Co-founded by Leo Wang, a second-generation bedding maker, Buffy combines decades of expertise with a commitment to reducing waste and water use.
Upgrade your Valentine’s sleep with Buffy’s Cloud Comforter, an all-season comforter, designed for softness, sustainability, and convenience. Made with a hypoallergenic TENCEL™ eucalyptus lyocell shell, it absorbs moisture faster than cotton and feels luxuriously smooth. Filled with 100% recycled PET fibers that upcycle approximately 50 plastic bottles, it’s lightweight, cozy, and machine washable. It features corner loops for secure duvet cover ties and even a 7-night free trial just to make sure it is a perfect fit. Retails for $125 at buffy.co.
