Upcycling Adventures: Turning a Shirtdress into Two Toddler Dress Shirts

I always thought that sewing for little boys was way less fun than sewing for little girls. No dresses, frocks, ruffles, or cute little accents. Just pants, dress shirts, and loads of straight lines.

When Kyriakos surprised us (me) by being a boy, my hopes for sewing matching little dresses and bows for Paisley and the baby were dashed. Before his birth, I’d even already begun to plan matching floral Easter dresses for “the girls” in my head.

But when I recently came across a piece of peach gingham fabric in a box of fabric that my grandmother gave me, my creative wheels started turning. Maybe I can’t have the matching girls in floral Easter dresses, but I can have matching boys in peach gingham ties. Oh, the cuteness!

Of course, little boys with matching ties need matching Oxfords to wear underneath them. I already have a simple Oxford pattern with plenty of sizes and simply needed something to make them with.

The Goods

Enter: a navy polka-dotted shirtdress of mine from the upcycle pile.

Both boys will receive a shirt from this polka dotted dress!
Colm prefers the solo modeling game.

First, I measure my boys to see which sizes to make. Colm measures slightly under the 18-month size, and Kyriakos measures a little below the six-month size. I stick with the slightly larger sizes so that they can wear them for (hopefully) a few months.

Then I get to work cutting up my shirtdress. I have to admit, this is a hard one to cut into because it’s one of those dresses that I absolutely loved to wear! But let’s just say that after having three babies and being blessed to breastfeed each of them, it’s a dress that’s simply not able to button modestly anymore. Ahem

I chop up the body and sleeves, which takes for-ev-er, since the dress is filled with pleats, darts, and other shaping details. I leave the collar and yoke alone, since they’re filled with even more stitch work to unpick. But I keep them on hand just in case I run into a situation where I need some more fabric for any reason.

Next, I lay out the dress pieces: two sleeves, two front panels, collars and stands, and one back piece and get to work matching up the pattern pieces to fabric sections. This is basically a giant game of Tetris, and I’m not sure whether I have enough fabric to go around.

The formerly pleated sections on the dress add to the complexity, since they have a slightly striped appearance that I don’t want on display somewhere like the front of one of the boy’s shirts. So I wiggle and move each pattern piece around probably a dozen times before I’m satisfied. And surprisingly, there’s just enough fabric to cut each piece!

Shirtdress back panel with multiple pattern pieces cut out.

The Process

I know that with two shirts in the same fabric, I am going to have to work extra hard to keep everything organized. After all, I don’t want to sew a six-month sleeve to an 18-month shirt and have to unpick my work a dozen times as I go. Plus, with two toddlers and an infant on hand, the constant interruptions cause me to lose my train of thought approximately 7 billion times a day.

To solve the organization issue, I store the shirt pieces in separate folders by size. Moving forward, I’m definitely going to implement the folder system for every project, because it keeps things tidy and I don’t have a dedicated sewing space, so I’m always moving in-progress projects from room to room.

I want to have the shirts done in time for Easter and would ideally like to have ties sewn by then too. But even with a month to get things sewn, I know I’ll be cutting it close.

Sure enough, I don’t get too much of the shirt construction until the last couple of days before Easter. My pattern starts with the shirt fronts, which means buttons and buttonholes [cue loud groaning here]. I have some adorable anchor buttons that match the shirt fabric perfectly.

Anchor buttons up close (with the addition of buttonholes).

Pesky Buttonholes

The buttonholes are another matter entirely. Technically, my sewing machine has an automatic buttonhole maker and foot, but it doesn’t work well (read: at all, even with interfacing), so I’m most likely going to have to make the buttonholes by hand.

When I try the sewing machine buttonhole foot, it partially sews one buttonhole onto a scrap piece of fabric and then quits. Handmade buttonholes it is.

Unfortunately, each shirt requires five buttonholes, so it takes me all morning and part of the afternoon on the Saturday before Easter to get the buttonholes completed.

With buttons and buttonholes in place, I can finally start on shirt assembly. For this I follow the step by step pattern instructions – times two – so I can get the shirts completed at the same time.

Even though the directions are pretty straightforward, I’m a slow sewist. The rest of the afternoon and evening pass and the shirts still aren’t finished. I plan to stay up to complete them so that the boys can wear them for Easter, but if I’m slow at sewing during the day, forget any kind of efficiency past bedtime.

I get to the sleeves around 10 pm and it’s just not happening. In fact, I do such a crappy job that I end up having to pick and resew two of the sleeves entirely. By close to midnight, I’m just done. The boys aren’t going to have cute matching shirts to wear for Easter, let alone adorable peach gingham ties (which I haven’t even started).

The Missed Deadline

Once my Easter deadline passes, I lose some motivation to work on the boys’ shirts. In fact, my sewing machine and all of my pattern paraphernalia sits on the dining room table for at least a week with the hope that “I’ll finish them bit by bit in my spare time”. Haha.

After a while of making my family eat dinner at the coffee table, I finally pack up the sewing stuff and move it to my desk, which has less space, but still isn’t the craft closet where projects go to die.

A few weeks later, I finally set my mind to finishing the shirts. Colm needs some new t-shirts and shorts, and I want to experiment with some upcycling for myself, which means I need to clear off my sewing table and get the boys’ Oxfords out of the way.

I pick the pattern back up and we’re to the collars and collar stands at this point. Let me tell you, this is not the easiest thing for a new-ish self-taught sewist to accomplish. After putting collars in and ripping them back at least twice for each shirt, they’re finally done. They’re not great. They’re not even good. But they’re done.

Then I’m supposed to put a button and buttonhole into each collar (boo hiss) and hem the bottom to finish the shirt. However, because these are my first structured shirts, there are some places where it’s evident that I’ve never done anything like this before. One of those places is the top of Colm’s shirt, where there is zero room for the child to both breathe and have a top button/buttonhole.

At this point, I’m simply happy to have the shirts done and wearable, so I forego the top buttons for both boys’ shirts. Of course, this means they can’t wear them with ties, but I find that the anchor buttons are cute enough for the front anyway. Plus, since they’re not wearing them to dress up for Easter, which was over a month ago, the formal shirt and tie combo isn’t really necessary.

The Takeaway

This project has taught me so much about patterns and fitting. Clothes are deceptively complicated – both tearing them apart and putting them together.

I complicated this project further by using a dress that had a ton of folds that my standard iron couldn’t completely erase. This turned simple seams into an origami challenge that’s beyond my current skill level.

Overall, I’m pleased with the shirts – mostly that they still fit my growing boys! They’re going to wear them for Mother’s Day and probably one (or both) of my brothers’ graduation ceremonies later this month. May’s a big month with plenty of special occasions for Colm and Kyriakos to show off their imperfectly mom-made shirts.

Kyriakos’ finished shirt.
The two shirts together (unfortunately it was breezy and they wouldn’t stay still).
Colm modeling his finished shirt! (He goes nowhere without his little French press 🙂 )
Looking like a computer programmer from the ’80s!
Both boys showing off their upcycled Oxfords.
The reality of a photo shoot with little boys 😉

What’s next on my upcycling table? A lovely casual dress made from… a vintage bed sheet!

Coming soon!
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Gabrielle Rystedt
Gabrielle Rystedt
Gabrielle Rystedt is a writer by day and a writer by night (because writers never sleep), who spends time balancing client orders, a couple of books and her blog at Raising Rystedts. She’s a business school grad who’s dabbled in management, both at the project and company level. She loves coffee and crafting, and enjoys settling down with a good book. Though as mom to three kiddos in three years, she realistically spends most of her time reheating her coffee and typing away like a crazy person on a laptop keyboard while surrounded by (clean) cloth diapers and cheddar bunnies.

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