With each passing year, I learn more and more about racing fashion and feel like I get better at putting my outfits together. This year would have to be my favourite one ever! I actually managed to have three outfits I was super happy with for Derby Day, Melbourne Cup and Oaks Day.

milano imai racewear melbourne cup

There is a lot more involved in a race day outfit than just choosing a dress, millinery and accessories. For many people, it involves the entire design process and making of a dress, the countless hours spent looking for the right clutch or colour shoe, trialing different options, having melt downs and a lot of time spent, simply, problem solving!

Personally, I think that the story behind a race day outfit is just as interesting as the final result. So, I’ve decided to share with you how my three race day looks for 2018 came about, with a behind the scenes adventure of each outfit.

This post (Part 1) will tell the story of my Derby Day outfit. Keep an eye out for Part 2 and 3 in the coming weeks, which will talk about how I created my Melbourne Cup Day and Oaks Day outfits.

My Designated Dress Maker

This year, as I have for the past four years, I enlisted Andrew Semple to help make my Spring Carnival outfits.

Andrew and I met 6 years ago when we were both studying Fashion Design at TAFE. I loved the design side of the course, and the embellishing, but was hopeless at patternmaking and sewing. After I left the course and started entering Fashions on the Field, I thought about Andrew and what a fabulous pattern maker and sewer he was. I contacted him a year down the track and asked him to make me a dress I had in mind for the races.

That was the start of our friendship and he is now my go-to dress maker for my race day outfits. Sometimes I go to him with an idea, fabric or a sketch of what I want. Sometimes he has something he has been working on. Together we have come up with some seriously epic dresses (if I do say so myself!).

outfit design guide diy style design white dress

My outfit design guide shows you the steps I took to make this white leather and lace dress.

When I first met Andrew, he was unfamiliar with the world of racing fashion. It wasn’t long before I had him immersed in it, turning up at his house talking about race fashion, discussing appropriate lengths, silhouettes, the styles I wanted to wear, along with dresses, hats and accessories.

We have come such a long way together, so I was so excited and proud of him when he was selected as just one of ten designers invited to compete in the Myer Design Award. And to top that… he succeeded in the incredible achievement of placing second runner up!! I am so very happy for him and I feel like he has found his calling as a dressmaker (extraordinaire) for race day ladies. He’ll be opening his clientele next year and I cannot recommend him highly enough.

myer design award andrew semple only one ashley

The Myer Design Award winners, Andrew with his model Brittney on the right.

He gets the fit of all my dresses perfect and is always willing to make any changes I want (even last minute). He is up to date with new trends and has some seriously fabulous fashion forward ideas. When we come together to work on a dress and play around with ideas, it’s always so exciting to see the final product, as it will always be a one off unique design, something I will cherish forever.

The Making of the Derby Day Dress

Derby Day is a really fun day to dress up for, with the challenge of wearing something black and white. This year I repeated an outfit I had made earlier in the year (by Andrew) and wore to Stradbroke Cup in Brisbane – the theme being black, white with a touch of red.

2018 derby day dress black and white fashion sketch

I sent Andrew a very quick sketch and had him make me a strapless full skirt dress out of black and white jacquard fabric, which I wanted to wear with a white ruffle sleeve shirt underneath from brand Harvey x Seeker. He did an amazing job whipping it up for me in a day- as I had left it to the last minute as usual.

There was no time to add boning, so I am thankful for my time spent working in a store called Kitten D’Amour. When I worked there I purchased waay too many corsets that I would never dream of wearing now, but I can sew them underneath garments as they provide the boning needed.

adding boning to dress using corset

I had added some red beads to the bodice to suit the theme of Stradbroke Cup, but replaced them with black beads for Derby Day. I like to add beads as I think it adds a touch of glamour. Or maybe it’s just that I can’t seem to help myself, I love beads!

milano imai black white stradbroke cup

The original red beads (sorry I forgot to take a close up photo of the red beading), and the new black beads.

beading embellishment diy black white floral print

The Making of the Hat

I knew I wanted a new wide brim hat for my outfit and had been swooning over this hat Louise Macdonald made for her Myer Millinery Award entry in 2017. The perfect excuse to get one made!

louise macdonald myer millinery award pink dior hat

Image: @wendellt, @louisemacdonaldmilliner

I contacted Louise in early August. I sent a fabric sample and we discussed colour options for the brim, crown, bird and feathers, sending emails back and forth and having Skype chats over the following weeks. Then I eagerly awaited to see the finished product.

millinery design process communicating with milliner hat maker

louise macdonald hat black white derby day in progress

black and white wide brim hat

You should always send your milliner a fabric sample, so they can match the hat material perfectly. Colours always photograph differently to how they appear in real life. It’s always a good idea to get progress photos so you know you are happy with how it is looking and can make any changes necessary early on.

black white hat cream bird white feather diy hat making

work in progress black and white hat

Originally, I thought about having a cream bird, but upon seeing it I decided to go with an all black bird with white and gold feather. My dress had a cream tone to it and the undershirt was stark white, so it was great to be able to incorporate the two colours in my hat to bring it all together.

milliner louise macdonald large hat box wide brim hat

This hat is such a big piece, and I mean BIG! You should see the hat box it came in! So, I didn’t want to have it posted to me, avoiding any risk of damage. This meant I didn’t see it till I arrived in Melbourne the night before Derby Day, when Louise dropped it off to me.

She gave me a quick lesson on how to repackage it and had reinforced the hat box with cardboard so that I could travel with it back to QLD, without worrying about the box collapsing or being damaged.

reinforced cardboard hat box

packaging millinery for safe travel no damage

Louise also makes this handy crown-like insert that your hat sits on top of so it doesn’t damage the brim or feather features.

I have to say here, I am in awe of Louise’s work and how well the hat was crafted, sewn together and secured. Being such a large brim, there’s always a worry of how it will sit on your head and how comfortable it will be, but this hat was incredible. It was stiffened so well, making it sturdy, with a cap-like piece that your head sat in. It fit perfectly and felt so light and secure, ensuring it wouldn’t be blown around by the wind.

sturdy secure well made fascinator hat

stitching close up details of millinery black and white derby day

I wasn’t the only one who was taken by this hat. Remarkably, Anthony Teva Dagorn, a patisserie working at the Conservatory restaurant at the Crown Casino in Melbourne, modelled my face and hat out of chocolate upon seeing my photos on my Instagram account!! That’s cool.

chocolate millinery sculpture Anthony Teva Dagorn patisserie Conservatory restaurant Crown Casino

Finding the Right Accessories

I purchased some shoes from Kookai because I thought the detail in the straps matched the lattice detail on the crown of my hat. My bag was a last-minute purchase from Bag Queen. My brother and his wife actually bought it for me as an early Christmas present and it arrived the day I flew out for Melbourne.

derby day accessories black heels bag clutch earrings

My earrings I found at Zara a month earlier- they actually have an amazing range of large statement earrings for a reasonable price- these were $25.

Getting my Hair Done

Every year I get my hair done by a fabulous lady in Melbourne called Rozi- @hair.by.rozi.

She really knows how to do a seriously big bun and even though my hair is only shoulder length and not that thick, she makes it appear extra voluminous. I always love a big bun style to match my hats and I love the way they stay in place all day.

I asked for a clean low bun to suit my big hat… how beautiful is this!

races hairstyles big bun silver hair

The Result

Here’s how it turned out.

milano imai derby day 2018 racewear

I was lucky enough to win my first Derby Day sash and my second ever Melbourne Cup week sash, scoring the second runner up place! Woo hoo! Felt like all my hard work finally paid off.