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4 ways I dress up my boys’ island-casual style for school

Every kid is different, and I’ve always been a believer in letting kids express themselves in ways that are creative and harmless. Pick your battles, right? One of my boys likes to feel put-together, wearing a button up shirt on days he’s just planning to hang out at home. Another one has trouble forcing himself to even wear a shirt. One of my four can’t seem to remember to wear shoes when we’re out, and another opts for the same two t-shirts day after day, even though his drawer is full of options.

Image: Monica Swanson/SheKnows

Finding the balance between giving kids freedom with their clothes, and requiring some standard code of dress when necessary can be tricky. But it doesn’t have to be painful.

We do love that Hawaii is known for its casual, easy-going style. You rarely see people formally dressed here, even in the corporate workplace. I tease my doctor husband that he chose to move here so he could wear an Aloha shirt to work every day instead of a shirt and tie.

Kids in Hawaii are raised in slippers (flip-flops), and some schools even still allow kids to show up barefoot!

Yep, Hawaii is very laid back, and we like it that way. It also means our shirtless, barefoot boys have the freedom to just be themselves much of the time.

Yet there is a time to look more refined and polished. When attending school or church or a special event, we want our kids to know when (and how) to pull it together!

Image: Monica Swanson/SheKnows

1. Make a short list of requirements.

In our home it might be:

  • a clean shirt with a collar.
  • a pair of long pants (no holes!)
  • shoes that cover the toe, (or on some occasions, nice and clean flip-flops are ok.)
  • Comb your hair!

2. Let them choose their shirt

Really, we are not going to love everything our kids wear, but if they are clean and tidy, then that’s good enough. The world knows that kids are always working through the self-expression thing, so unless a shirt is offensive or not in good shape, let them go with it!

3. Give them quality pants options

Make sure they have pants that fit well (no kid wants to be seen in high-waters!) and if denim is acceptable, let them rock some jeans! Jeans are socially acceptable in most situations, and paired with a nice shirt, denim can look really classy! My boys’ go-to attire this fall across-the-board are Levi’s® 511™ Slim Fit jeans and a stylish Aloha shirt.

4. Let them know how great they look

Compliment your kids when they dress up and give them lots of encouragement for putting themselves together. A little goes a long way!

All of our boys have grown to enjoy dressing up when they need to, especially when they get to add their own personal style to their look.

Image: Monica Swanson/SheKnows

As you shop for your guys this fall, consider pairing Levi’s® denim with a button up shirt or a classic Aloha shirt. The 511™ Slim Fit is on sale now at JCPenney starting at $39.99. Sending you much aloha and happy back-to-school vibes!

This post is sponsored by Levi’s®.

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