Transforming Men’s Wear into a DIY Checkerboard Dress

  • 4-min read
  • 12 Tools
  • Intermediate


I had so much fun on this DIY project!

I was able to partner with the uber-talented Veejay Floresca on a challenging, but fun, thrift-flip. Veejay is a Filipino fashion designer based in LA who does custom work and makes everything from streetwear to bridal!

She challenged me with transforming a men’s blazer, dress pants, a button-down shirt, and a sweater into something I would wear.

I saw the below inspiration and new that I had to make a chic DIY checkerboard dress.

This was an opportunity to expand upon my patchwork experience, give old garments a new life, and practice sustainability while flexing my creative muscles.

I hope it’ll be the same for you.

So, let’s dive in!

LittleToh - DIY Checkerboard Dress - Before Image - Tiffany wearing a men's suit and shirt LittleToh - DIY Checkerboard Dress - After Image - Tiffany wearing a black and blue checkerboard dress with grey ties.

Tools & Materials

Just a reminder that my original video is in the middle of the page. You can watch the entire process and read the entire transcript there if you’re interested .


Before we start, we need to prepare our materials. This involves seam ripping all the items so we can start fresh. This process might seem tedious, but it’s a necessary step to ensure we have a clean slate for our project.

Once the items are seam ripped, it’s time to decide on the design of the dress. For this project, we’re going for a checkerboard shift dress – a simple yet stylish design that’s perfect for showcasing our creativity.

Creating the Checkerboard Pattern

The first major step in our project is creating the checkerboard pattern. This involves cutting the fabric from the pants and the blazer into squares. This step requires precision and patience, but the result is a visually striking pattern that will serve as the main design element of our dress.

Once the squares are cut, they are sewn together to create the checkerboard pattern. This process might take some time, but it’s a great opportunity to practice your sewing skills and create something truly unique.

Modifying and Using the Dress Pattern

Next, we need to modify and use a dress pattern. For this project, we’re using a basic shift dress pattern as our base.

However, we’re making some modifications to fit the design of our dress. This involves adjusting the side seams, lowering the armholes, and modifying the section where the straps are sewn on. Once the modifications are made, we cut out the pattern from our sewn-together squares. This step brings us one step closer to seeing our dress come to life.


Hello everyone, welcome back to my channel. Today, I’m going to show you how to make DIY easy fabric covered buttons. So, let’s get started.

Hello everyone, my name is Tiffany and welcome or welcome back to my channel. If you like sewing and DIY videos, make sure to give this video a thumbs up and subscribe to my channel. I am back with another upcycle by little toe where I take all forgotten items and give them a new life and if you saw my last video you’ll know that I’m doing a month of thrift flip challenges featuring some of my fellow Asian creators to celebrate AAPI Heritage Month.

This is the second challenge video in my series so if you haven’t seen the first one I’m gonna make sure to link it down below but this week I’m so excited to be collaborating with my new friend Veejay Floresca. Veejay is such an amazing designer, she’s based out of Nelly and she makes everything from streetwear to Bridal and here she is to introduce herself.

Hi, my name is Veejay Floresca and I’m a Filipino fashion designer from California. I am very happy to do this collaboration with Tiffany because we have the same passion. I love upcycling sustainability, I do a lot of one-of-a-kind pieces and also I do custom work for our clients. I hope that this collaboration will show you my work and I hope that you will also support my channel. Thank you so much.

If you saw my last video you’ll know that we have a $10 budget to thrift one or more items for the other person to flip so let’s get started. I’m packing up the things to send over to Veejay right now and you already know I’m not gonna show you everything but I wanted to give you all a little sneak peek. She says she likes solids so I’m gonna send over these that are kind of solids but like a sassy solid. She is such a talented fashion designer so I’m so excited to see what she makes so make sure you check out her video to see exactly what I said to her and to see what she turns it into.

The package that Veejay sent me just arrived all the way from LA and she sent me a message a couple of days ago saying that she chose fabrics that were challenging so why am I so nervous. I’m just gonna go ahead and open this and I’m really excited to see what she sent. Okay, okay, I see that there are a lot of solids which I don’t normally work with but I am definitely up for this challenge so I know the stuff in this box smells so good.

There is a lot of what I would categorize as office wear so I’m really excited to work with this but she also sent me a sweater which is a knit and I have I want to say zero experience working with knit but I did say I wanted something challenging so I am really excited about this. Here is a closer look at the things that she sent me and first up is this Navy men’s Blazer that fits me really well honestly. She also sent this gray button down and these black men’s dress pants that I personally love the fit of so I’m kind of bummed that I have to cut them up and finally here is a better look at the sweater she sent me.

I am just trying to decide on what to do with all of these items and this sweater is really throwing me off because I really have never worked with knits before so I’m struggling a little bit to try to figure out what to do. I’ve had a few days to think about what I wanted to do and I’m not gonna lie this one was super challenging for me but I think I finally have an idea of what I want to make.

I also realized that I don’t really talk about my process of figuring out what to do in my flips but one of the things that I’m really conscious about during my brainstorming phase is making sure that I make something that I actually want to wear. I was feeling really stuck with these items and at one point I thought okay you know what I’m just gonna crop the Blazer but realistically I don’t think that I would wear a cropped Blazer very often so I decided to just go ahead and seam rip everything so that I could start fresh except for the sweater because that’s still a big TBD.

I want to make something that’s me so I decided to make a dress and here are some of my inspiration photos. I’m gonna make a checkerboard shift dress with the materials from the pants and the blazer because those are pretty similar in weight. This is the pattern that I’m going to be using as a base. I haven’t really decided if I want to keep the pattern as is or if I want to make some modifications but if I do I’ll definitely show you how I make them.

You all have seen me do this a ton by now but I never cut my patterns and I always trace out the size that I need and based on my measurements, I went with a size 8. I did make a small modification to the back bodice. You can see here that the original pattern has a slight curve in the center back but I wanted mine to be cut on fold so my Center back is just a straight line. I also decided to shorten my pattern. I went ahead and made the mock-up and I just pinned out some ribbons to help hold the dress on for now and I did decide to make some modifications to the pattern.

I don’t want to sew in a zipper for this dress and I also need to find a way to incorporate this gray shirt into my design and I came across this picture of this top that has Ties on the side so I think I’m going to use this gray shirt to make ties for my dress. Because I’m adding the ties I’m going to have to modify the side seam and you can see here that I’ve only sewed this side seam together till right below my waist and I’ll take this whole section and fold it under and I’ve done the same for the back panel creating this open V and I’ll mirror this on the other side as well.

I am also going to make a modification on the straps because I’ve decided to use the Hem of the sweater as my straps. I think my strap are going to end up being about an inch and a half and the original pattern has skinny straps so I’m just going to make this adjustment to accommodate the wider strap. I want to show you all of the modifications that I made so here is the original front bodice pattern I traced out and here is my modified version.

You can see here that the side seam has been adjusted and I’ve also lowered the armhole by about an inch. I also marked the point to where I want the side seams sewn chill but the biggest change I made was to this section where the straps are sewn on. Here you can see how I made the adjustment to accommodate for a wider strap. Moving on to the back, here is the original pattern and here is my modified pattern. Again, I’ve adjusted the side seam and lowered the armhole slightly. I made the adjustment for The Wider strap and I also decided to lower the back into this u-shape.

Now that the pattern for the dress is done, I’m gonna go ahead and cut the fabric from the pants and the Blazer into squares. This took a significant amount of time but that’s okay because this is my podcast time so send me some recommendations. I’m currently listening to murder with my husband and I am obsessed with True Crime. Anyway, here are all of the Navy and black squares that I cut out from my front panel and I so wish this is how fast it actually went but here it is all sewn together.

Here is my front bodice pattern and here it is cut out. Next is to sew on the darts and this is what it should look like at this point. I wanted to quickly mention that the original pattern also has darts on the bodice to make the dress a little bit more fitted along the waist but I’m not going to add that Dart to my dress because I think I want it to fit pretty Loosely. On to the back, here is the piece I sewed together and here is my back bodice pattern. I’ll cut this out and next is to sew the darts on the back.

This is what the back panel should look like now and I’m just placing my front piece right sides facing and I’ll sew these together from this point to the Hem and repeat for the other side. Here is what the dress should look like now with the top section not sewn together along the side seams. Moving on, I cut this piece from the shirt to use as my side tie. I’ll fold this in half right sides facing and I’ll sew together along the top here. Here it is sewn and it’s a little hard to see but I’ve pressed it so that the seam allowance is in the middle of the tie. Now I’m going to sew this end together and here is the Tie pressed and turned to the right side.

Following the same steps, I went ahead and made three more of these long ones and then four shorter ones as well. Next is to sew these onto the dress. I’m just pinning the longer tie closer to the top here and then pinning the other side as well and then I pin the shorter tie closer to the waist and again I’ll do the same on the other side. I’ll repeat this again on the back again pinning the longer ties towards the top and the shorter ones towards the bottom. Now I’m going to go ahead and sew all of these Ties on and this is what the dress should look like at this point.

Next is to sew on the lining that I made from the gray shirt and I’m just inserting the shell layer in between the lining layers so that they are right side spacing. You have no idea how relieved I am to sew in this lining. The fabric from the pants in the Blazer phrase so much and because it’s Patchwork there are just so many raw edges and it looks so messy and I don’t want to be dramatic but it was causing me severe anxiety.

Starting with my front layers, I’m just pinning the shell and lining together making sure to carefully tuck the ties in between both layers. Then I’ll sew together up the side seam and around the armhole stopping at this point. I’m going to skip this section here and then I’ll start again from this point and sew along the neckline to this point. Again, I’ll skip this section here. I’ll start sewing again here along the armhole and down the side seam on this side as well. I’ll repeat all of these steps for the back layers.

Here is what the dress looks like turn to the right side and here is what the inside looks like. I’m just tying the ties into bows and next step is to sew on the straps. I cut off the Hem of the sweater to use as my straps but as you can see here it is very stretchy and I need my straps to have a little bit more structure so I’m just going to use bias tape and I’ll sew them along the edge and this actually kills two words with one stone because not only will it give it more structure but it’ll also cover the raw edge. Here are both of my straps and I’m going to start by attaching them to the back of my dress which is turned to the wrong side.

I’ll start with one of the straps and I’m just feeding it in between the shell and lining layers and then pinning it in place. I’ll repeat these steps with the other strap again feeding it through the layers and pinning in place. I’ll sew these on and here is what the dress should look like with the straps attached to the back. Now I’m going to attach the straps to the front of the dress and I’m just pinning them in place and then I’ll sew these on.

Here is the final look. I am so happy with how this turned out. I was really nervous about this one because I was working with materials that I don’t normally work with but I think it turned out really well. I love the checkerboard pattern and I think the gray ties add a nice pop of color. I also really like the open sides and the back and I think the sweater straps are a nice touch. I hope you enjoyed this video and I’ll see you in the next one.

Sewing the Dress Together

Now, it’s time to sew the dress together. This involves sewing the darts on the front and back bodice of the dress, which helps shape the dress and give it a more fitted look. Then, we sew the front and back pieces of the dress together along the side seams, leaving the top section open. This open section will later be used to attach the ties and the straps.

Adding the Ties and Lining

The next step is adding the ties and the lining to the dress. The ties are made from strips cut from the shirt, and they’re sewn onto the dress to add a stylish and functional element.

adding the ties to my diy checkerboard shift dress

The lining, made from the same shirt, is then sewn in. This step not only gives the dress a clean finish but also adds an extra layer of comfort.

Attaching the Straps

Finally, we attach the straps to the dress. The straps are made from the hem of the sweater, giving them a unique look and feel. They’re attached to the back and front of the dress, completing the transformation of our men’s wear items into a chic dress.


And there you have it – a stylish checkerboard shift dress made from a men’s blazer, dress pants, a button-down shirt, and a sweater.

This project is a testament to the power of creativity and the potential of upcycling. Not only have we created a fashionable dress, but we’ve also given new life to old garments.

So, why not give it a try? Grab those old clothes, dust off your sewing machine, and let’s create something beautiful together.

If you liked this article or projects like this, please follow me on Instagram and YouTube for more images and videos of my work. It means the world to me and is free!

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As always, thank you so much for reading, and happy upcycling!

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