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Fashion Style Guide to Selecting Cute Winter Outfits for Kids

Winter weather is a little different everywhere you go. In the North, kids typically bundle up while in the South there is more layering of lighter clothing. Being from Wisconsin, I am used to very chilly winters, but where we live in North Carolina, the winter wear is different. Since we have moved around, and know a lot of others who do too, I decided to pull together a fashion style guide with 10 secrets to selecting cute winter outfits for kids.

This post is sponsored by Everywhere Agency on behalf of OshKosh B’gosh; however, all thoughts and opinions expressed are my own.

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We all know winter clothing has to be about a little more than just fashion, but thankfully OshKosh B’gosh has some super cute winter outfits for kids that are both stylish and have a purpose. Whenever we shop there, we always find what we need for the season (and we shop there a lot.).

Cute Winter Outfits for Kids Square

10 Secrets to Selecting Cute Winter Outfits for Kids

Finding clothing that will both keep kids warm and comfortable during the winter season is a must. Here are some of our tips for making your clothing selections:

1. Photo Ready

Lights. Camera. Action! The winter season usually is paired with a lot of photo taking. Whether the kids are playing outside, unwrapping gifts, or taking part in an actual family photo session, make sure their outfits are photo ready. We love choosing wintry styles for the kids and adding layers (which is especially great if one layer has hot cocoa spilled on it–take that layer off or add a layer over top and you’re good to go for pics!).

Jeans are a great basic item to have available because they work well for everyday and go well in pictures too. We also love sweaters and comfortable button-up tops.

We used our OshKosh clothing photos for our Christmas cards and will be sending some of these adorable pictures to their daddy who is overseas!

Minted Cards Close

2. Play & Party

The winter months are usually filled with a lot of play and a lot of party. Having friends or family over and baking cookies? Kids having a friend over to play? Hosting a semi-formal Christmas party the kids need to look dressed-up for? Try layering a graphic tee underneath a nice sweater jacket. The tee is comfortable and light enough for serious play time and the sweater can be buttoned up over top to make the look dressier (and photo ready too!).

Cute Winter Outfits for Kids Long

3. Indoors & Out

Not only will the kids want to play indoors, but they will also likely want to head outside to run around or play in snow. Here is another place where layers really come in handy. Depending on the weather, we usually layer a graphic tee with a fleece jacket with a light winter jacket then maybe accessorize with a pair of gloves and a hat. OshKosh has all the winter weather essentials too!

Cute Winter Outfits for Kids  Tree
Cute Winter Outfits for Kids  Tree 2

Indoors during the winter, a lot of homes have the heat cranked up, so you will come inside from the freezing cold and get overheated. We love having heavier layers for outside, but still having a lighter layer underneath so we can take off a couple layers and stay comfortable. Usually a graphic tee (short-sleeve or long-sleeve) works well for this depending on where you live.

4. Your Area

We all live in different places and the weather can change significantly depending on where you live. When we lived in Wisconsin, we had to bundle up a lot more for winter than we do here in North Carolina. When we lived in Virginia, we bundled up and were prepared for a little more than we are now, and the list goes on.

If you have lived in an area for a long time, you probably already have gotten used to your typical winter wear and know how to set up cute winter outfits for kids. A lot of times, if you are used to colder weather, you don’t even bundle up as much as others may if they are visiting. I know there were times in Wisconsin that I would go outside in a t-shirt in the middle of winter. I may not have stayed outside like this long, but I did like having lighter clothing options available.

New to an area? Maybe you are moving around a lot for a job, as a military family, or just because. Get to know the area you are new to so you can be prepared with cute winter outfits for kids that are actually beneficial to keeping your children warm.

Winter Wear Map USA

I have also put together this graphic above to help you out. I polled people from all over the United States to get an idea of basic winter wear for kids where they live or have lived and grouped similar states together. It may not be completely accurate (I can’t draw exact boundary lines for weather changes and different kids are comfortable with different outfits), but I hope it gives you a great general idea of what to buy when looking for cute winter outfits for kids.

OshKosh B’gosh is great at having a good selection of clothing that is perfect for winter outfits for the kids near each OshKosh B’gosh location. We love layering their clothing here, because we have days that are hot and days that are completely freezing. Just the other week it went from the 50s to the 70s to the 40s in three days!

5. Vacation Destination

Traveling over the holidays? Don’t forget to take into consideration the weather you are headed into, especially if you are headed somewhere a lot warmer or colder than you are used to. When we visit back home in Wisconsin or Virginia, we usually bring some heavier winter gear along with us because we know it is a lot colder.

6. Crazy Weather

Being prepared is always a good idea. There may not usually be a huge snow storm near us or in Virginia, but having at least one heavier item would be a good idea just in case. The same goes with having at least one item out for unseasonably warm weather. We like finding some of the summer clothing on the clearance rack at OshKosh B’gosh and picking up colors and designs that are more basic and work during the winter season.

7. In Season Styles

My favorite part of finding cute winter outfits for kids is picking up clothing that is in style for kids fashion. OshKosh Kids always has stylish clothing that fits what is popular and it is pretty conservative. We shop there all the time for the boys and always find outfits that are stylish for winter pictures and comfortable for play.

Cute Winter Outfits for Kids  Back

8. Coordinating

When you are layering, it is important to coordinate your clothing for color, pattern, and designs. You don’t need to wear all gray like we chose (I just loved the style combo), but think about groups of colors that work well together for the winter season–gray with blue and white, red and green with gray or tan, silver and pink with white, and green with brown all work well.

We like to choose clothing based off of what will coordinate together into several outfits, rather than shopping for each individual outfit. For more tips, read my Kid Fashion | How to Layer Outfits post or how we put together Over 150 Outfit Combos with Under 20 Pieces of Clothing.

9. Comfort

Kids really do have to be comfortable. This means soft fabrics and clothing that keeps them the right temperature and not overheated (this can make anyone crabby) or freezing (this can be dangerous or cause kids to get sick.). Finding comfortable and cute winter outfits for kids is also ideal if you want to get all those nice pictures. If your child finds an outfit too restricting or too warm or too scratchy, you will likely not get the amazing pictures you had hoped for.

Cute Winter Outfits for Kids  Secret

My kids love helping choose clothing from OshKosh B’gosh and we are sure to try them on in the fitting rooms before purchasing to make sure they are comfortable in them and everything fits okay.

10. Discounts for the Pocketbook

EXPIRED: New clothing every season can get expensive, so I always love shopping for deals. OshKosh B’gosh always has nice sales and their coupons and rewards program are a bonus. Here is an exclusive coupon for 25% off your purchase of $30 or more! Online Code: OKBG3223. In Stores: Show the image below.


Bonus: Sweet Memories

Seeing those cute winter outfits for kids and the smiles on your kids faces as they celebrate the holidays and enjoy all that winter has to offer will make you want to capture those memories forever. My kids jumping for joy! They are so excited for Christmas and all the activities we will be doing!

Cute Winter Outfits for Kids  Jump for Joy

Read Documenting Memories | Journaling Your Moments for fun ways to document these memories so you can reminisce for years to come.

What does the typical winter outfit look like by you and where do you live/what state? Share with me in the comments!

Read also: Kid Fashion | How to Layer Outfits and Handprint Christmas Tree Framed Wall Art

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OshKosh B'gosh Giveaway

One lucky winner will receive a $50 OshKosh B’gosh Gift Card.

Entering is simple! Complete the mandatory entry. After this, complete as many entries as you want to earn more chances to win!

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Disclaimer: Arts & Crackers is not responsible for any accidents that may be caused by use of this product. This giveaway is in no way sponsored/endorsed by Facebook, Twitter, Pinterest, or Google. No purchase necessary to enter. Void where prohibited by law. All entries will be verified; invalid or incomplete entries will be discarded–Arts & Crackers is all about honesty. Please do not just “unlike” or “unfollow” pages after the giveaway. Giveaway open to legal residents of the USA and ends at 11:59 pm EST on 12/18/2016. Winner will be chosen at random and have 48 hours from the point of notification to claim his/her prize.


  1. I love shopping at Oshkosh for my grandsons. They have cute good quality clothes and good sales.

  2. Love shopping for little boys! Less expensive than girls!

  3. Such great tips and I love the adorable clothing!!

  4. I enjoy shopping at Oshkosh for my kids. They have great styles for both boys and girls.

  5. I love the cute clothes that I find while shopping at Oshkosh.

  6. oshkosh has so many nice outfits. they make it easy to put nice outfits together. thanks for the great tips too!

  7. I love the cute clothes they have at OshKosh and they are very affordable!

  8. We are all sweatered-up!

  9. I haven’t bought snow boots since we moved to Missouri but we still use sweaters, winter coats, gloves, and scarves. I do love to shop at OshKosh for our grandkids. The styles are so cute!

  10. We love sweaters and flannels in South Carolina. OshKosh has the cutest clothing!

  11. Here in Ga we usually wear long sleeves sometimes a jacket but jeans and boots or tennis shoes!

  12. We wear a lot of Hoodies and jeans in Upstate, NY 🙂 I love the athletic clothes that Osh Kosh has for my son 🙂

  13. Such great quality clothing-especially for “ruff and tumble” little boys! Wonderful giveaway, Thank you, Susan

  14. I love shopping at OshKosh B’gosh for my son.

  15. Sweaters, jackets, and a good pair of pants are great for the winter. We live in Texas, but it still gets cold! 🙂

  16. This would be great to win for my grandson! I love OshKosh!

  17. We’re in Michigan — we wear sweaters, coats and boots from November to March. Would love to get the Red Cardigan for my Granddaughter.

  18. Usually a great graphic tee, soft sweater, knit hat, jeans, & gloves make the clothing scene here in Texas. The weather can change from morning to night so layering works best.

  19. Pinetrest wouldn’t allow me to pin your pin link. I tried over and over so I pinned from your Pinterest link on the left of your site. I hope you will give me credit.

    • So weird! Thank you for letting me know. I’ll try to take a look at it and see if I can figure out what’s up. You definitely still get credit 🙂 Thanks, Pam!

  20. I like their large selection and cute age appropriate clothes.

  21. Being in the Phoenix are, winter outfits here usually include pants, shirts with sleeves, and shoes (as opposed to shorts, tanks and sandals), with the occasional sweatshirt when it gets colder.

  22. Oh I love shopping at OshKosh. They have such great quality of clothing! I know that the clothes we buy, will last! They always have such great sales too!

  23. Hello Alyssa, These secrets are great. Really this is a helpful blog for me. I followed these secrets recently and get praised by others for selection of outfits. My kids are looking stylish and trendy in this outfit. Thank you so much.

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