Back-to-School Without the Scramble: A Wardrobe Checklist That Actually Works
- Bonnie Southwick

- Jun 29
- 4 min read
August has a way of arriving faster than anyone plans for. One week you're in full summer mode and the next you're counting down days and realizing your kid has outgrown half their wardrobe since May. We've seen it happen every year.
The good news: you don't need a lot to start the school year well. You need the right things. Here's a checklist built around what actually gets worn, in a Florida climate, for real school days.
The Everyday Foundation
Start here. These are the pieces that carry the week:
Soft tees and long sleeves in easy, mix-and-match colors
Comfortable bottoms: shorts, leggings, or pull-on pants they can move in
At least one lightweight sweater or zip-up for overly air-conditioned classrooms
A play dress or easy set for the days they want something a little different
Keep the palette simple so everything works together. Fewer decisions in the morning mean smoother mornings.
For soft, easy tops and bottoms that mix and match effortlessly, my go-to brands are Zuccini Kids, The Beaufort Bonnet Co., Hatley, Bisby, Properly Tied, and Prodoh. These are the pieces that hold up, wash well, and actually get reached for.
The Florida Layer Problem
It's 68 degrees at drop-off and 85 by lunch. Florida parents know this drill better than anyone. The fix is lightweight layers that can come off easily and get stuffed in a backpack without becoming a wrinkled disaster.
A thin cardigan, a zip hoodie, or a long-sleeve tee under a jumper covers the morning chill without overcomplicating the outfit. These are the pieces worth investing in because they work every single day from August through March.
Right now I'm reaching for the quarter-zip pullovers from Southern Tide, the Hayward Half Zips and Cassidy Comfy Crewnecks from The Beaufort Bonnet Company, and a classic white cardigan from Feltman Brothers. All excellent. All proven.
One or Two Special Pieces
Every kid deserves something in their closet that makes them excited to get dressed. It doesn't have to be expensive or elaborate. A twirly skirt. A graphic tee from a brand they love. A color that makes them feel like themselves.
These are the pieces that make Monday mornings slightly less of a fight. Pink Chicken, Blue Rooster, Bisby, and Queen of Sparkles (a new brand for us this year!) always bring that element of fun. For boys, I'm loving the graphic tees and coordinating shorts from Properly Tied, and the Prepletic shorts and tops from The Beaufort Bonnet Company. Comfortable through the first hot weeks of school, and sharp. For girls, a knit play dress from The Proper Peony or The Beaufort Bonnet Co. is hard to beat: great colors, easy patterns, and genuinely comfortable all day.
Don't Forget the Accessories
Accessories are a low-cost way to make an existing wardrobe feel new again. They also give kids some say in how they look, which matters more to them than we sometimes remember. Here's what we have in the shop right now:
Shoes: Native Shoes (a new brand for us this year) and Jack Rogers sandals.
Bows and headbands: Wee Ones, in all colors and styles.
Hats: Bits & Bows, including the Amelia Island and 32034 hats they designed exclusively for Monkey Barrel. Those are personal favorites.
Belts: Web belts from Preston in a range of colors and designs, and brown leather belts from Southern Tide.
Socks: Classic white fold-over socks, white socks with eyelet trim, and white and navy ruffle knee socks, all in stock now.
Bloomers and playground shorts: Wundershorts playground shorts in white and navy, and classic white eyelet bloomers to wear under dresses.
Sunglasses: Polarized WeeFarers in black, white, tortoiseshell, pink, purple, red, blue, and turquoise.
Backpacks: The most important back-to-school accessory. Apple of My Isla makes coated, durable backpacks in Camo, Florals, Stripes, and Patterns. Cute and built to last the year.
Picture Day Is Coming
Worth thinking about now rather than the night before. An outfit that photographs well, holds up in the Florida heat, and doesn't require ironing is a specific thing. We have those.
One thing most parents don't realize: school pictures are almost always photographed from the waist up, so the top is what matters most. If your child will be photographed against a plain background, a sweet bishop-smoked dress or a blouse with embroidery and a cute collar works beautifully for girls. For boys, a bright polo or a button-down, solid or patterned, reads great on camera. If the background has a lot of color, a solid top or dress is your safest bet. Come in, and we can help you find something that works for the photo and the rest of the day.
The Checklist
3 to 5 tees or tops in easy colors
2 to 3 bottoms or dresses they'll actually reach for
1 to 2 lightweight layers for cool mornings
Comfortable shoes they can wear all day
A few accessories to finish the look
One special piece that makes them excited to get dressed
A backpack built to last the year
Stop by Monkey Barrel before school starts. We'll help you fill the gaps, skip the scramble, and send them off feeling ready.








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