Back-to-School Essentials for Teens & Tweens at DICK’S Sporting Goods

Back-to-School Essentials for Teens and Tweens at Dick's Sporting Goods header image


It’s no secret that I love back-to-school shopping for cute teacher outfits! But as a mom of three boys who do not love shopping, getting their back-to-school essentials has always been a bit of a hassle. This year, now that I’m down to just one kiddo left at home to shop for, I finally discovered that it doesn’t have to be a chore! Despite the fact that Jay, my 12-year-old, does not enjoy shopping and won’t wear jeans because they’re “too uncomfortable,” getting him all set for the new school year was a breeze. The solution? One-stop back-to-school shopping online at DICK’S Sporting Goods!

NOTE: This blog post contains affiliate links. Shopping via these links means I may earn a small commission at absolutely no cost to you. As always, all opinions expressed here are 100% my own, and I only share products and brands that I love and think you will, too. I received a DSG giftcard in exchange for sharing about my back-to-school shopping experience in this post.

Back-to-School Essentials

This year, Jay and I sat down to make a list of what he needed for school aside from school supplies, which we order through our school. He needs some things because the ones from years past (or that were handed down from his older brothers) have finally worn out. Other things, like shoes and water bottles, get worn out during the course of the year and need to be replaced more frequently. Here’s what we came up with:


Then I handed my laptop over to Jay and let him look around at DICK’S Sporting Goods. I was tempted to peer over his shoulder and make suggestions like I normally do, but I decided to step back and let him make his own picks. After all, we could find alternatives later if I didn’t agree. Surprisingly, I was okay with everything he chose.

Choice = Cool, Comfy, Confident Teens/Tweens

He ended up doing a great job! DICK’S Sporting Goods was a one-stop-shop with all of the sporty styles and brands he loves, so he found everything he needed pretty quickly. The items he chose are not in the style I would have chosen, but I think that’s the point. Once we finished ordering the items, he said, “I can’t believe I had fun doing my back-to-school shopping this year, and I got the coolest stuff that I actually want to wear!” Choosing his own things makes him feel cool, comfy, and confident. In years past I think he just got tired of shopping and ended up agreeing to whatever I picked out so we could be done…resulting in him not really liking any of it. Not this year! I consider this a huge win. Most tweens and teens are capable of making these types of choices given a list, a budget, and a few parameters.

Here are the items he chose, along with some other great options for your tweens and teens. I focused on picks for guys here just because, well you know, boymom.


Jay loves the outdoors, so this Carhartt backpack was the very first thing he chose. I think he had it picked out in about 60 seconds flat. His typical backpacks usually last 1-2 years, but this one is built to last and may still be slung on his back when he heads into high school two years from now.

Jay’s Pick: CARHARTT Legacy Standard Work Pack

Dick's Sporting Goods Carhartt Legacy Standard Work Pack

My Picks:

Jay with Carhartt Legacy Standard Work Pack

Water Bottle

DICK’S has nearly infinite choices for water bottles (Hydro Flask, anyone?). Jay loves the Gatorade bottles because they fit in his backpack and don’t add a lot of weight to it. When he saw this camo one, he knew it was the one for him.

Jay’s Pick: GATORADE Gx 30 oz Bottle

GATORADE Gx 30 oz Water Bottle in Digital Camo

My Picks:


We always go through drawers and closets to weed out any clothes that don’t fit before the school year starts. This way, we know what holes there are in the wardrobe and don’t buy duplicates or unnecessary items. One feature of the DICK’S Sporting Goods website that helped inspire Jay’s choices was the curated looks for teens featuring graphic tees, stylish hoodies, utility pants, flow shorts, footwear, accessories, and more from top brands like Under Armour, Nike, Jordan, Adidas, Carhartt, and The North Face. They also have VRST, a new private label line made specifically for men as well as DSG, a private label line designed to be inclusive, affordable, and stylish. I love that 1% of the purchase price of every DSG item is donated to the DICK’S Sporting Goods Foundation’s SPORTS MATTER program to help save youth sports.

Jay’s Picks:

My Picks:

I have too many to share! 😀 Just go here and check out all of the curated looks for teen/tween guys, girls, and kids. If your kiddos love sporty-comfy-cool stuff as much as mine, you’re good to go. So many great ideas!

DICK'S Sporting Goods Curated Looks for Teens and Tweens Guys Men


Kids’ feet grow so fast! And as a mom of two adult sons, I can tell you this is not going to stop until they’re in their early 20s. DICK’S carries all the top brands of running shoes (a must for school sports!). They also have tons of the most popular lifestyle sneakers. Fun side note: they even have a SNEAKER RELEASE CALENDAR for upcoming launches of key sneaker brands like Jordans and Yeezys! Jay isn’t into Jordans or Yeezys, but he does love low-key lifestyle sneaks that are comfy and cool.

Jay’s Pick: NIKE Court Vision Shoes

Nike Court Vision Sneakers in White and Gum

My Picks:

Jay in North Face Apex Elevation jacket, Carhartt Sweatshirt, and DSG Commuter Pant, and Nike Court Vision Shoes

Fall/Winter Coat

Last, but not least, it’s important to have a coat for when the weather suddenly turns cold. Cold snaps have caught us unprepared more than once, but not this year! Jay wanted something water- and wind-resistant and cozy so he’ll be able to play outside to his heart’s content. There were a lot of options, but we picked this one from THE NORTH FACE. Plus, the brown color he liked was marked down 25% lower than the rest – SCORE!).

Jay’s Pick: THE NORTH FACE Apex Elevation Jacket

The North Face Men's Apex Elevation Jacket in New Taupe Green

My Picks:

Jay in Carhartt Logo Sweatshirt, DSG Shorts, and Nike Court Vision Shoes

KISS: Keep It Simple, Sweetheart

I kind of like the good old K-I-S-S acronym to remind myself that life doesn’t have to be as complicated as I sometimes make it. Back-to-school shopping for Jay at DICK’S Sporting Goods this year took about 30 minutes. Total. It was quick, painless, affordable (if you find a lower price anywhere, they’ll match it!). One stop and done: easy-peasy! DICK’S makes it even easier with free shipping deals to ship it home. They also have free contactless curbside pickup if you’d rather pick it up. Best of all, as Jay pointed out, he “actually” got things he liked this year and had fun doing it. For us, this was an awesome way to knock out our back-to-school shopping list and #WELCOMEBACK to school!

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Teacher Outfits to Mix and Match

LOFT Back to School Teacher Outfits 8 items, 16 outfits for teachers header image

LOFT Loves Teachers + Teachers Love LOFT

Time to head back to school again! Whether you’re a brand new teacher or a battle-tested veteran like myself, it’s always fun to freshen up your teacher wardrobe as you prep for the new school year. In the same way a new pair of workout leggings can inspire you to get into the gym, putting together a new teacher outfit is one small way to infuse a little excitement into back-to-school season. Whether you’re looking for trendy new items or classic basics, you are going to want to check out LOFT. They are known by teachers far and wide as the destination for affordable quality pieces that are perfect for teachers’ on- and off-duty lifestyles.

And the hashtag #loftlovesteachers isn’t just marketing. LOFT offers teachers a 15% discount (use your school/district issued email address to sign up), and they support teachers through DonorsChoose. During August 2021, They are collecting money in stores now through September 13, 2021, and they will match up to $50,000 in donations.

Note: This post contains affiliate links. Shopping via these links means I may earn a small commission at absolutely no cost to you. As always, all opinions expressed here are 100% my own, and I only share products and brands that I love and think you will, too. Thank you so much for supporting my small business.
LOFT Striped Ribbed Midi Dress and Denim Jacket with White Reebok Sneakers image

Teacher Closet Staples to Wear All Year Long

Today I’m sharing 8 stylish, teacher friendly items at LOFT and how I will be mixing them into my wardrobe now and throughout the school year. For my back-to-school picks, I stuck with colors that can be mixed and matched with each other as well as with the rest of my clothes. You’ll notice lots of neutrals with a few pops of color. For reference, I am 5’5″ and typically a size M/8.

The 8 LOFT Items:

  • 8 LOFT items to shop
  1. Striped Ribbed Midi Dress – Perfect alone or layered! I got my typical size M, but could have sized down.
  2. Flecked V-Neck Pocket Cardi – True to size: wear it with EVERYTHING (great for taming overzealous air conditioning and winter drafts).
  3. Spacedye V-Neck Cardi – More of a cropped look; size up for a roomier (or a bit longer) fit.
  4. Spacedye Sweater Tank – Also slightly cropped; true to size. Great alone or with the matching cardigan as a twinset.
  5. Curvy Midrise Straight Crop Jeans – True to size or slightly roomy. They hit at my ankles, but I rolled them for a bit more of a cropped length.
  6. Lou + Grey Wafflestitch Henley Top – True to size or slightly roomy. Suuuuuper soft, as you would expect from Lou + Grey. Can be dressed up or down just like the matching pants.
  7. Lou + Grey Wafflestitch Wide Leg Pants – True to size, and nice and drapey. You could dress these up with heels, run errands with some kicks, or lounge around the house. I haven’t worn wide leg pants for years, so these feel fresh.
  8. Denim Trucker Jacket – Fits a little small on me (not much stretch). They also have some “oversized” denim jackets, which are trending now, on the website.

16 Mix + Match Teacher Outfits

Here’s how I styled these cute pieces! This dress would also be cute with a blazer or kimono. You can wear it to the beach over a suit or dress it up for Back-to-School night! It also comes in solid olive, and it’s sooooo soft and comfy.

Outfits featuring the LOFT Striped Ribbed Midi Dress

Remember those sweater sets from back in the 90s? They’re back! Twinsets have a classy Audrey Hepburn type vibe, and I love that you can wear the pieces as a set or individually. They’re great with jeans, a skirt, or shorts in the summer!

LOFT Spacedye sweater set with cardigan and sweater tank

I’ve been all about the joggers this past year, so these wide leg lounge waffle knit lounge pants feel fresh and different. You really could wear these anywhere!

LOFT Lou & Grey off white waffle knit set with henley top and wide leg pants teacher outfits

Finding jeans that fit well and are comfortable can be a struggle. The LOFT “Curvy” jeans have a little extra room in the hips and thighs, so they don’t gap around the waist like a lot of jeans do. These aren’t distressed, so they’ll be great for school as well as weekends.

LOFT Curvy Midrise Straight Crop jeans teacher outfits

You really can’t go wrong with LOFT. They get new arrivals frequently, they have great sales (as I type this they currently have a promo code for 60% off!), and their clothes are very well suited to the classroom and to real life. Teachers, good luck with the new school year!

For more ideas for cute, comfy teacher outfits, check out @everydayteacherstyle on Instagram or these other posts:

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