Cameron – Top: Childrens Place Bottoms: Children’s Place  Shoes: Nike (sold out), similar here 
Calvin – Top: Children’s Place | Shorts: Children’s Place Shoes: Keen 
I can’t believe I am seeing back to school items already. Geesh! I feel like school just let out.  It’s so bittersweet for me.  On one hand I will be happy to get Cameron back in school, and on the other it just means that he is going to another grade up and closer to not being my little kid.  🙁 He is starting third grade in the fall, and I like to get a jump start early on school shopping.  I always like to beat the rush and before items get picked over.  Plus I have found that I find better deals on clothing in July versus August. 
Fortunately for me Cameron’s school has a school supplies ordering system where you just pay a flat fee.  This will get him all the school supplies he needs to get going for the first day of school.  I like this concept as it gives me one less thing I have to run around for. Looking forward to only having to run out to get clothes and a backpack.  We are going with Pottery Barn Kids for the backpack this year.  I love their styles, and want to get a more durable backpack.  Last school year we had to get 2 due to them wearing down so quickly.  

Regardless, I have a boy that grows like weeds and it requires me to seasonally restock his wardrobe with clothing, undergarments, and shoes.  And since I have a toddler that is in the 100% percentile for height and weight you can imagine how quickly he grows out of things as well.  About 2 (3 if needed) times a year, I will just stock up on both boys.
We do one bulk shopping trip for the boys, and this will get them stocked up for a couple seasons.   This has helped with budgeting, so we are not every other week having to run out and buy something for them.  It has helped me stay organized on the items I purchased and what they still need.  I don’t know how many times I have bought shirts for them close to something they already owned because I forgot.  Before we do the big shopping trip I take inventory of what the boys already have.  I check for holes and what still fits.  This helps me create my list for what each boy needs. We then will donate the items that no longer fit to make space for their new items.  

When we do our shopping we will knock out everything. Shirts, undies, socks, pants, coats, shoes.  activewear (Cameron), and of course his backpack. EVERYTHING! 

Here is a list of the stores I shop at when it is time to stock up on the boys, and what I purchase from each store. 
Children’s Place
I would say I shop at Children’s Place the most for the boys. I get the most bang for my buck.  Plus they have such a variety of clothing and always run deals for free shipping along half off items. Some of the items that are I almost always get from them are below:
Graphic tees– You can almost always get them for like 3-4 dollars.
Underwear- I am still at the point where I am not ready for Cameron to be in big guy plain style underwear. They offer in his size underwear that is still cool colors/patterns for his age.
Khakis– I get most of their khakis from here because they are are like $10 dollars. 
Sleepwear– Again, I am not ready for either of my boys to grow up quite yet. lol! So they both still wear pajama sets. They offer them in Cameron’s size, and have the cheapest I have seen sleepwear.  
Be careful with purchasing jeans from CP, they don’t last as long as others companies.  The knees always end up getting holes after a season.  However, they are so cheap that I still get them.  I snagged 3 pairs for Cameron for $7.99 each.  It may just be my rowdy 8-year old with this problem. 
This place is an all-time favorite.  They are consistently bringing cute items and vibrant colors for both boys. I would go as far to say that they have the cutest boy clothes (not every store caters to boy fashion) I frequently shop at.  I do not shop their as much as CP, only because the price point.  Gymboree does frequently have sales, and offers coupons with free shipping.  Join their mailing list if you like Gymboree but not the price point.  Even with the coupon it is still higher in price, but definitely worth it. Also, if you are looking a dressy look this is where I get all holiday and picture clothes for the boys. 

Old Navy
I love Old navy.  However, their kids items are not always cheapest when not on sale.  So wait until they have their kids items on sale.  Another thing, I still really love ON for Calvin, I am just not that into the fashion as much for Cameron, he’s 8.  ON doesn’t match his style quite as much, I do still get basic tees there for Cameron.  Again, I do not shop at Old Navy for the kids unless they are having a sale. Their regular price point is higher than other stores. 

Osh Kosh

Let me say I don’t shop here a ton in the summer for the kids.  I prefer their Fall and Winter apparel.  I love their Osh Kosh sweat suits for Calvin.  When I go into Osh Kosh my main purpose is to get jeans.  They have quality and sturdy jeans.  Cameron almost weekly will come home with a hole in his jeans, and I realized that I had to get a sturdier type of jean. You will pay a little bit more compared to other stores, but it is worth it for rowdy boys. 
For the boys shoes I don’t have one particular store I get their shoes from.  I like to get all the major colors for each of them.  I will get a black, red, blue, brown dress shoe, and gray.  Cameron wears orthotic inserts in his shoes, so I try to get shoes that offer the most support.  I focus on that first before I think of brand or price.  A few places I check is Finish line, Famous Footwear, and Stride Rite.  It is so hot in TX that I keep Calvin in Keen Sandals.  They are sturdy and supportive but let his feet breathe.  I love them! I will also be taking advantage of the Nordstrom Anniversary Sale! They have kids shoes for majorly discounted price.  I have linked some of my favorites that are part of my back to school shopping list. 

Another place I frequently get clothes from for Cameron is Nike, he likes their sportswear.  With him in sports all year round I do like to stock up on athletic wear as well.  I don’t necessarily shop at the Nike store, because sometimes other stores will have Nike gear at a more affordable price. 

I love putting my boys in cute clothes at an affordable price.  The age my boys are at right now I don’t get them the most expensive shoes or clothes.  I just cannot justify it considering Cameron literally came home one day with a giant hole in his shoes that were bought less than a month ago.  They are just to rough with clothes.  It will be a rare finding when you see my boys in Polo or Jordans at this stage of the game.  Definitely do what fits your budget the best!
Regardless of your budget I recommend making a shopping list so nothing is forgotten or duplicated! If you feel like you always are running out getting a new item for the kids, consider migrating to condensing your shopping trips to one bulk purchase.  It has helped me organize their clothing and simplify my life.  
Good luck!