With the colder season now upon us, many parents may be concerned about how to properly dress their kids to avoid getting sick from dropping temperatures. But fashion and function need not be mutually exclusive. In today’s Spend vs Save edition, we’re looking at boys’ fashion that will keep them warm and comfy this season. Before we dive in, here are some amazing layering tips from Kindercare. First, your base layer must be the first thing your child wears and must have a moisture wicking purpose. Materials that are great for this are wool or synthetic fabrics, such as polyester. The fit should be snug. The purpose of middle layers are to insulate. So on top of your base layer, put on some wool, down, or fleece that should fit right but not constrain your child from moving. Lastly, an outer layer must protect from rain, snow, and wind. Such materials that are great for outerwear are a waterproof jacket or shell or those made with Gore-Tex, a breathable fabric. Here are some suggestions to consider mixing and matching this cold season.
Little boys’ fashion: Jackets for Fall and Winter
Spend: The North Face Chimborazo Reversible Jacket
Let your handsome boy travel in style this season of family reunions and getaways with this Chimborazo reversible jacket, which features a durable taffeta and plush interior so you can have two functional pieces in one. It features Heatseeker™ insulation that works both ways to ensure he stays warm however the jacket is worn. Features a front zip closure with chin guard, front pockets, and is made of 50D 73 g/m² 100% recycled polyester with 200 g/m² 100% polyester lining. Get 25% off at Nordstrom.
Customer review: “Love that it’s lightweight but warm and that the good fits around his head so that the wind doesn’t blow in. It doesn’t cover his eyes either.” Wilde1
Save: OshKosh B’Gosh Boys’ Reversible Midweight Jacket in Space Print/Wedgewood Blue
Let your little astronaut show off his love for space with this super fun reversible jacket from OshKosh B’Gosh, which features a cute printed puffer and a hood to keep him warm on chilly days. It has a front zipper closure, hood,and all over space print that’s perfect to go with any of his tees. The interior is a gorgeous blue that’s bright and fun to wear as well. Rated 5 out of 5 stars on Amazon.
Customer review: “This has been the perfect jacket for winter here in Northern California. My son is 2 1/2 and tall, and he normally wears a 3T. The jacket fits really well with a little room to grow. I’d say that this is about true to size.” K.
Spend: Chaser Galactic Tacos Cozy Fleece Sweatshirt
If like you, your son is into Mexican food, he’s going to adore this fun fleece sweatshirt from Chaser. It features a mouth-watering feast of space-traveling tacos that will surely blow his mind (and maybe his tastebuds, too!) This sweatshirt is made of 49% polyester, 46% rayon, 5% spandex. Shop at Nordstrom.
Save: Spotted Zebra Boy’s Toddler & Kids 2-Pack Crew Sweatshirts
For families with several kids, save up on clothing expenses with this 2-pack set of crew sweatshirts from Spotted Zebra. Each sweatshirt features bold graphics and soft fleece that make them a choice piece for the colder season. It features a pull on closure and ribbed cuffs and hem for a perfect fit. Spotted Zebra offers unique clothes for boys and girls who are ruled by their imagination. Their collection of personality-packed pieces come in easy to mix-and-match options that are stylish and fun to wear, no matter what the season. Shop at Amazon.
Customer review: “Great quality! The fabric is very soft inside and out, and remains so after multiple washings. Warm and cozy. Great quality and excellent value.” Kairi
Spend: Hurley Polar Protect Fleece Zip Hoodie
Go for an athletic look with this hoodie from Hurley that is fitted with supersoft fleece and an easy-on zupper and hand-warming front pockets for easy wear and utmost comfort. It features a split kangaroo pocket and is made of 100% polyester for great comfort and durability. Shop at Nordstrom.
Save: Bumeex Boys Sherpa Fleece Lined Jacket
Featuring soft, breathable, comfortable material, this soft fuzzy jacket will be your son’s new favorite article of clothing this cold season. Its interior fur is made of soft 45% cotton and 55% polyester blend and its lining is made of 100% polyester. It features smooth quilted wadded fabric, zipper closure, and a thick construction to keep the cold away. Its stylish colors are very reminiscent of a varsity jacket, which makes it perfect for wearing to school and to the playground. Rated 4.8 out of 5 stars on Amazon.
Customer review: “Great quality, super soft inside and thick. I got this for my son to grow into for next winter. Since I don’t put him into heavy puffy coats in his car seat and we live in the midwest where it is cold, I thought this was a perfect option!” Anne Pollpeter
Jeans and Pants
Spend: Hudson Jeans Jude Skinny Jeans in Superfly Wash
Whether it’s for school or for weekend family gatherings, this pair of pants will make your little man look sharp and dapper. These skinny jeans are cut from soft, stretchy denim for easy mobility and wear and comes in a versatile dark wash that’s perfect to be worn with any top and jacket. Features a zip fly with button closure, five pocket style, and is made of 71% cotton, 27% polyester, 2% elastane. Shop at Nordstrom.
Save: Nautica Boys’ 5-Pocket Skinny Fit Jeans
If you’re going for the classic, choose Nautica’s skinny fit jeans that adds a versatile style to your child’s closet. It features a 5-pocket design with a slim leg and a button fly closure. Rated 4 out of 5 stars on Amazon.
Customer review: “These fit my lil guy great. He’s approx 35” tall and 28lbs. There are buttons on the inside to cinch in the waist. Cute pants for my active toddler.” Bethany
Spend: DL1961 ‘Brady’ Slim Fit Jeans in Ferret
This dapper pair of jeans from DL1961 is a smart choice for both school or play. These slim-fit jeans feature a classic five-pocket style paired with just enough stretch to keep active kids comfortable. It is also designed with DL1961’s Active-X 360-degree technology that helps keep the fabric keep its shape even after many washes and wears. Features a zip fly with button closure. Made of 62% cotton, 36% Tencel® lyocell, 2% Lycra® spandex. Shop at Nordstrom.
Customer review: “These are the best jeans for my grandson. He is so skinny and we have such a hard time finding jeans for him. The adjustable waist is great so they stay up and don’t fall down. The dark denim is classic and the fit is perfect.” Teel00
Save: Levi’s Boys’ 511 Slim Fit Performance Jeans
When it comes to long-lasting quality, you know you can trust Levi’s. The brand’s legacy is built on classic and durable fabric, inspiring them to create comfortable clothes for kids that are designed with intention and upholds strict ethical standards. Just like the Levi’s 511 jean, which is designed for peak performance, wherever the kids go. It features a comfortable regular fit from the hip to the ankle and a signature 5-pocket design with arcuate stitch on the rear spade pockets for a classic look your little fashionista will adore. This pair is made of soft, stretchy denim and 23% recycled plastic bottles so you know you’re helping the environment! It also features moisture wicking fabric that keeps him dry and comfortable, while soil release technology makes cleaning and washing a breeze. Rated 4.4 out of 5 stars on Amazon.
Customer review: “These pants fit perfectly on my 4 year old son. I bought him a size 5T. He has thick thighs and the fact that they are soft, stretchy, and have an adjustable waste option was perfect!” Erica C. Brown
Spend: Tucker + Tate Pull-on Jeans in Seattle Fog Wash
For comfortable wear wherever your little one goes, go for this easy-fitting drawstring waisted pants from Tucker + Tate. These jeans are made from soft, stretch denim that are comfortable as soon as he wears it. It features a five-pocket style. Made of 98% cotton, 2% spandex. Shop at Nordstrom.
Save: The Children’s Place Baby Boys’ Pull on Jeans
Growing little boys may not have time to deal with buttons! Good thing there’s The Children’s Place and their line of pull on jeans that are made with 100% cotton and features hand-sanded denim for a lived-in, abraded look. It features a traditional fit in the hip and thigh, as well as a straight leg. It has an elasticized rib-knit waistband made of 85% cotton and 15% viscose and a drawstring that ties at the center waist. Its pull on closure makes for super easy wear, especially when you’re in a hurry. This best-seller is rated 4.5 out of 5 on Amazon.
Customer review: “Our first outgrew these quickly, but our second’s had more seasonal match, and they’ll be great to pass along again now that he’s about outgrown them. There’s a super-conscientious waistline on these, and I’ve never heard a grumble putting them on, which is not true of most of the tops and bottoms my threenager’s vetted after summer.” Jessica
Spend: Hatley Black Bears Button-Down Shirt
Perfect for dinner at grandma’s, this button-down shirt from Hatley is great paired with khaki pants and boots. It features black bears roaming around its all over print of this classic button-down shirt that’s made of 100% soft cotton that’s comfortable to wear. Features a front button closure and button chest patch pocket. Shop at Nordstrom.
Save: Amazon Essentials Boys’ Long-Sleeve Poplin/Chambray Shirt
Also perfect to pair with some khakis, this poplin/chambray shirt from Amazon Essentials is a classic, casual, weekend-ready piece that your son will love to wear all season long and beyond! this lightweight button-down shirt features a special wash for a soft feel and maximum comfort. It also features a spread collar, rounded barrel cuffs, a box pleat, and a chest pocket. Rated 4.9 out of 5 stars on Amazon.
Customer review: “This is a very lovely shirt for a boy. It comes true to size and fits well. The fabric is soft and has understated design that would fit with any pants/jeans. It’s not overly long so it would not need to be tucked in. The stitching and buttons are sturdy and of good quality. It would suit for school or special occasion. I really like it. I recommend it.” Gerbera
Spend: Volcom Caden Plaid Shirt
Plaid never goes out of style, especially in the Fall. This gorgeous button down shirt with long sleeves is made of 100% lightweight cotton that’s easy and comfortable to wear. IT features a front button closure, button cuffs, and a chest patch pocket. Comes in three colors you’ll love to add to his wardrobe: Bison (pictured), Red Deep, and White Flash. Shop at Nordstrom.
Save: Hope & Henry Boys’ Long Sleeve Brushed Cotton Flannel Button Down Shirt
Made of organic cotton that is free of pesticides and insecticides, this button down shirt from Hope & Henry offers a more affordable alternative to safe clothing for kids. It is made of cotton that’s produced using conventional production methods and features a style that is easy to wear. It’s made of hefty shirting weight flannel featuring richly colored classic plaids that’s perfect to pair with jeans, khakis, shorts, and more. Each side is suedeed to create a soft and lofty finish that resists pilling. Also features buttons at the pocket, cuffs, and placket for a classic, polished look. Rated 4.7 out of 5 stars on Amazon.
Customer review: “My son wore this until it didn’t fit any more. The quality of material is exactly what we expected and it didn’t shrink when we washed it.” Amazon Customer
Spend: Mini Boden Monster Sweatshirt
This cozy pullover from Mini Bowden features a snow-dwelling creature that’s ready to intimidate with this mouth that opens or shuts! This fun interactive sweatshirt will definitely be the talk of the next children’s party. Featuring a crew neck and long sleeves, this sweatshirt is made of 80% cotton, 20% polyester. Shop at Nordstrom.
Save: Dealone Baby Boys Dinosaur Pullover Sweatshirt Crewneck Cotton Long Sleeve Tops
Your little one will be saying “See you later, alligator!” with this fun pullover sweatshirt that features a classic round neck design. It’s comfortable and soft to the touch, making it easy to wear this Fall and Winter seasons. It is made of 95% cotton and 5% spandex for just the right amount of stretch. Its fun design adds a dose of personality to this piece that he’ll love to wear til it’s worn out. Rated 5 out of 5 stars on Amazon.
For more great fashion ideas for boys and kids, make sure to check out the links from our archive below.
Just a disclaimer – We have partnered with these companies because we use their products and/or proudly trust and endorse them – so we do receive a commission if you make a purchase or sign up for services. Often, we are able to negotiate special discounts and/or bonuses, which we will pass on to you via our links. We often get short notice on sale items available for 24-48 hours as we will pass these savings onto you.