Sweater Weather Streaming: 20 Classic Cozy Movies

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As temperatures drop, curling up with a great movie is becoming more tempting. While a spooky movie or an action-packed thriller might add some excitement to your evening, a heartfelt movie is perfect for a cozy night. Sweater weather calls for classic tales of romance and poignant family dramas. Here are twenty that are perfect for chilly evenings at home.

The Holiday

Amanda Woods, a movie producer from Los Angeles, and Iris Simpkins, a columnist from London decide to trade homes for a short vacation. Once they switch places they develop unexpected relationships that just may change the course of their lives. Both women have been unlucky in love. But when Amanda meets a charming neighbor and Iris makes a new friend in LA, will their luck change? The Holiday is a delightfully sweet movie with a fantastic cast that’s a perfect option for dinner and a movie in the comfort of your home. 

Practical Magic 

Sally has vowed to never love again but when rushes to rescue her sister Gillian from a dark romance that’s turning deadly, a new person enters her life and makes her question everything. The Owens sisters have endured bullying for generations and have learned to stick together. As the pair finds themselves in over their heads, they struggle to find a way out of their mess and reimagine a future for their magical lineage. Sisterly love and second chances propel Practical Magic, a 90s classic with an ethereal aesthetic and a compelling plot. 

Brown Sugar

Dre and Sidney fell in love with hip-hop together as children. But could they have a deeper connection? In Brown Sugar, we follow Dre and Sidney as they follow their love of hip-hop. Life takes them in different directions but their hearts keep pulling them together. Can they find a way to honor their passions and find a way forward together or do they need to go their separate ways? Brown Sugar showcases Black love against a backdrop of a rich musical landscape. It’s a must-see movie. 

The Photograph 

The Photograph tells the story of a young woman, Mae who learns about her late mother, Christina’s, life by inheriting a box shortly after Christina’s passing. Through reading a letter left in the box for her, Mae uncovers her mother’s inner world and begins to establish a bond with her.  As Mae discovers more about her mother, who was once an iconic photographer, she is approached by Michael, a journalist who is writing about Mae’s mother. Micheal and Christina grow closer and come up against their histories and hang-ups to figure out how to move forward in love. 


B.A.P.S starring Halle Berry and the late Natalie Ann Desselle-Reid is an outrageously adorable movie about two friends who fly to California to pursue their dreams. They are deflated quickly after an audition goes south, but their luck changes when they are approached by someone offering to pay them handsomely to pose as the distant family members of a wealthy man. This classic comedy is available on Hulu with the Showtime add-on. It’s an unforgettably funny journey with an ending as sweet as the relationships that develop along the way. 

Reign Over Me

After losing his wife and children in a tragic terrorist attack, Charlie Fineman is drifting through life as a shadow of himself until he reconnects with his old friend in Reign Over Me,  streaming now with Hulu’s Showtime add-on. Charlie’s old friend, Alan Johnson, is a dentist who’s struggling to meet the challenges of maintaining a family and a business. Alan tries to support his friend while respecting his boundaries and what follows is a heart-wrenching and deeply bittersweet story about friendship and grief that will blow you away. 

The Lake House 

Sandra Bullock and Keanu Reeves play people who fall for each other while living two years apart in The Lake House, a sleepy little classic based on a South Korean film called Il Mare. When Dr. Kate Forster sells her lakehouse in 2006 and writes a letter to the new owner, she wasn’t expecting that her letter would somehow travel back in time to 2004 and that an amazing new friend, Alex Wyler, would come across it. As they start sending letters back and forth and discover that they are in two different years they begin to explore how they can connect and defy their realities. Will they find a way to maintain their relationship across space and time? 


Transitions in families can bring all sorts of issues to the surface and that is illuminated in the blended family at the center of this family drama. Stepmom, available on Hulu, tells the story of a family transitioning after a divorce and the challenges around the children accepting their new stepmom Isabel, played by Julia Roberts. The kids, Anna and Ben, have a hard time adjusting and things become even more challenging when their assertive no-nonsense mother Jackie, played by Susan Sarandon, shares a devasting secret. What springs forth from these challenging circumstances is a story about love and forgiveness that will warm your heart. 

Notting Hill 

Notting Hill is a sweet and odd classic romantic comedy. Although it’s over 20 years old the love story at the center of the movie is timeless. Julia Roberts is a charming movie star that has a chance encounter with Hugh Grant at his travel bookstore. From there they have a romance that endures the slings of the paparazzi, a series of unfortunate events, and eventually, they have to decide whether to let go of their pride and let love reign. 


Infamous playboy Marcus Graham, played by Eddie Murphy, meets his match in Boomerang, a hilarious and fast-paced classic romantic comedy. After a romantic encounter with his new boss, Jacqueline Boyer, his world turns upside down and he is forced to reconsider his entire way of life. What results is a delicious moment where the tables have turned and he learns that there may be a bit more to love and relationships than he originally thought. 

You’ve Got Mail 

Before smartphones and streaming services, Kathleen Kelly and Joe Fox connect over email in You’ve Got Mail. Kathleen is a small bookstore owner and Joe is posed to take over her block and her business as the owner of a large corporate chain.  When they meet in real life, unaware of their virtual connection, they are at odds, until Joe uncovers the truth. When Joe gets closer to Kathleen he is faced with a choice, reveal his identity and profess his love or play it safe and maintain his friendship with a lie? You’ve Got Mail is a feel-good film, available on Hulu, starring Tom Hanks and Meg Ryan that may make you roll your eyes but will also warm your heart. 

The Proposal 

When austere businesswoman, Margaret Tate, enlists her employee Andrew Paxton, to pretend to be her fiancé to avoid deportation, she is forced to meet his family in Alaska. Their fake engagement sets off a wild ride chock full of hilarious moments. From midnight sing-alongs to gut-busting moments with the grandmother, and so much more this film will have you in stitches. The Proposal is a light-hearted romantic comedy that you should definitely add to your Hulu favorites. 

Sleepless in Seattle

A young boy calls into a radio show and attempts to find love for his grieving father, Sam Baldwin, a year after his mother’s death. Women nationwide are enamored by the father and looking to connect with him but he is not ready to move on. One of these women is Annie Reed, a reporter from Baltimore played by Meg Ryan, who just might be the one if they can ever meet long enough to have a conversation. Sleepless in Seattle is a slow burn with a satisfying ending and a story that will make you believe in love available on Paramount Plus. 

The Vow

What if you were in an accident that wiped your memory and you forgot everything about your life? How would you deal with a loved one longing to be remembered? In The Vow, Paige Collins, played by Rachel McAdams, is dealing with that exact situation. When Paige is injured in a terrible car crash, she forgets everything, including her loving husband Leo, played by Channing Tatum. Can she fall in love with him all over again? The Vow is based on a true story and explores how the relationship develops after the accident. It’s a heartwarming tale about the power of love. 

Maid in Manhattan

Maid in Manhattan, available on Hulu, follows Marisa Ventura, a level-headed working-class mother, hoping to move up the ranks at the prestigious Beresford Hotel in New York. When one spontaneous choice leads to Marisa crossing paths with handsome politician Christopher “Chris” Marshall, she poses as a wealthy guest. Will he lose interest when he finds out what she does for a living or will they ride off into the sunset together? Maid in Manhattan is a lovely light movie that is a great addition to a cozy season movie list. 

Last Holiday 

Georgia Byrd, played by Queen Latifah,  is a cautious sales associate at a struggling department store. When she learns that she only has a few weeks to live, she decides to go on a lavish vacation. While on vacation in Europe she makes a group of well-to-do friends, including the owner of the department store. As her vacation comes to an end and her new friends learn more about her, Last Holiday, streaming now on Paramount Plus, tells a beautiful story about living life fully and cherishing each moment.

The Fundamentals of Caring 

Trevor is a young man in need of a caretaker, Ben is a writer in need of a job. What could go wrong? Trevor is a wisecracking yet sheltered kid looking for an adventure so when his new caretaker Ben, suggests a road trip he’s eager to go. The trip sets in motion a series of bizarre events that build their friendship, help Trevor to come into his own, and teach them both about vulnerability and courage. The Fundamentals of Caring is an endearing movie that will make you laugh as much as it makes you cry. 

Saving Face 

A pregnant widow is forced to move in with her lesbian daughter and their relationship is put to the test in this romantic comedy steeped in Chinese American culture. Saving Face is a witty and entertaining story that touches on the trials and tribulations of mother-daughter relationships and breaking with convention. 

The Water Man 

Eleven-year-old, Gunner Boone and his mother Mary, played by Rosario Dawson are trying to fit in after moving to a small Oregon town in The Water Man. Gunner’s father, Amos, struggles to connect with his son but can’t seem to bridge the gap between them. Between dealing with his mother’s leukemia diagnosis and feeling isolated from his father, Gunner is seeking out friendship and adventure when he comes across a town legend and a fast-talking friend, Jo. A mythical creature that threatens to destroy a small town leads a young man with a big imagination and his streetwise friend on an unforgettable adventure. The pair face challenges large and small as they gear up to go head to head with a dark force as they forge a powerful friendship. 

Where’d You Go, Bernadette? 

When Bernadette is confronted with an impossible choice she makes a decision that upends her family and sends her husband and daughter on a mad dash to find her. Where’d You Go, Bernadette?, streaming now on Hulu, is a beautiful film that explores themes of loss, familial relationships, and the pursuit of seemingly impossible dreams. It’s a hopeful yet emotional story that is perfect for a night in. 

Have you seen any of these cozy classic movies? They are all available on streaming services and will take you on an emotional journey from laughter to tears and back again from the comfort of your carefully crafted blanket fort. Treat yourself to a bowl of something comforting and a movie marathon. You won’t regret it.