How to dress for Melbourne Cup Day

Nikki ParkinsonFashion, How to 42 Comments

In two weeks’ time you’ll either be waking up fresh as the day or wondering why your fascinator is still attached to your head.

Yes Stylers, the race that stops a nation is off and runnning in under two weeks.

Are you planning to be at trackside at Flemington in Melbourne, at a fancy lunch or at a low-key gathering with your girlfriends?

If so, this post is for you.

This post is also for two SY readers who both wrote asking for some Cup Day fashion advice.

My friends and I tend to enjoy the fun of Cup Day at a big fancy lunch, with a fashion parade, some champers and of course the fun of sweeps and the race.  Now they have included “fashions on the field” and “best fascinator”.  Oh dear, the stakes have been upped.  I don’t feel confident enough that I would actually win, but heck, I would really enjoy being in the running. – Lesley

I am losing sleep and spending too much time on websites trying to solve my spring racing fashion outfits. My dilemma, I am a size 18 (oh ok, probably closer to a 20) and 43 years old. There doesn’t seem to be much out there this year. For racing I like something tailored (without looking menopausal or mother of the bride) or edgy. Past racing seasons have seen great luck from brands like Trelise Cooper, Nicola Waite, Euphoria, Moss Design. Part of the problem is it seems many things around aren’t dressy enough or seem to be a reprise of years past. – Marika

In my former life, I spent many a race day judging fashions on the field.

It was a task that had plenty of highs and way too many lows.

The highs came from witnessing women who had put a lot of thought and planning into their outfits and who were polished to perfection. The lows came from women who may have planned their outfit but hadn’t planned to keep away from the champagne tent before judging.

Which leads me to my 10 style tips when it comes to how to dress for Melbourne Cup Day.

10 Melbourne Cup Day style tips

1. Keep it classy. Race days are steeped in tradition and that tradition should be honoured. It doesn’t mean a dowdy approach to your race-day outfit but it does mean that your dress shouldn’t be mistaken for a top. And it does mean staying relatively sober should you be entering fashions on the field.

2. Plan your outfit starting with the dress. I once had to find the outfit for a client to work back with a hat she’d fallen for (hello Sue, I love that you’re still getting wear out of that outfit BTW!). It can be done but it’s a whole lot easier to find the dress and then buy the hat (or have it made) to suit.

3. Headwear is a must. A hat, fascinator or headpiece … it’s not a race day outfit without one. If at a function indoors, err on the smaller side so as not to knock out the person sitting next to you. Trackside? Go to town on the size factor and make a statement with it.

Melbourne Cup Day casual lunch styling idea

1. Lee Cooper for Big W dress $35 | 2. Adorne cuff $10 | 3. Colette Hayman fascinator $19.95 | 4. Missoni for Target wedge $69 | 5. Katies clutch $49.95

4. Invest in a one-off piece of millinery. This isn’t a possibility for everyone but if it’s a statement you want, then this is the way to go. Ask around for recommendations or contact your local TAFE to see if there are any student milliners near you whose work is cutting edge yet undiscovered. Want more wear out of your head piece or hat? Opt for a design in a neutral base but with coloured adornments you could have changed later for a different race day outfit.

5.  It’s spring so your outfit should reflect that. Traditionally Melbourne Cup Day fashion is associated with a whole lot of colour. If you’re doing the entire Spring Racing Carnival in Melbourne then by the time Cup Day rolls around you will have already trotted out your black and white for Derby Day and have an ultra-feminine number ready for Oaks Day. Outside of Melbourne, you can definitely get away with a Cup Day outfit that is monochrome or girlie – just make it fun and fabulous with your own spin on it.

6. Match but don’t match. You want all the elements in your outfit to complement each other but you’re not going for a matchy-matchy scenario. Your bag doesn’t have to match your shoes and your hat. Your bag might pick up a colour from your dress and your shoe colour might feature in your hat but they don’t all have to be the same hue.

Melbourne Cup at the track

1. Maiocchi dress $299 @ Birdsnest | 2. Gregory Ladner hat $169 @ Myer | 3. Louenhide clutch $89.95 @ Birdsnest | 4. Samantha Wills ring $79 | 5. Siren heels $139.95 @ Styletread

7.  Choose your footwear wisely. It’s never a good look to leave a Melbourne Cup Day function – or the races – barefoot and carrying your shoes in your hand. Wear shoes you know you can go the distance in. This isn’t so much of a consideration if you’re just going out to lunch and then doing the school pick-up but it most definitely is if you are trackside.

8.  If buying a new dress, buy something that you know you’ll wear again. Ideally you already have an event or occasion coming up during the party season where you know you’ll be able to trot it out without the headwear. And if you work in an office, maybe it’s something that this time next year will join your work wardrobe. Thinking of a dress purchase this way means that if it initially costs more than you would normally spend, its value will be in the distance it goes in your wardrobe.

9.  Book in with your hairdresser. If you haven’t already done this and are planning attending a fancy Cup Day function, stop reading and make the call. Your headwear might look best with an up style – or you may just need expert help in securing to your head so it lasts all day.

10. Your makeup should go the distance. Primer is your friend, as is a long-lasting foundation, smudge-proof mascara and either a gloss you can easily re-apply or a long-wear lippy. Get it right at home and all you’ll need in your clutch is a lip colour and maybe some pressed powder. Oh and if you’re at the track or spending the day semi-outdoors, pile on the sunscreen.

Melbourne Cup Day lunch event

1. Lala Belle dress $229 | 2. Blue Illusion fascinator $69.95 | 3. Olga Berg clutch $89.95 @ David Jones | 4. Tony Bianco heels $159.95 @ Styletread | 5. Mimco bangle $99.95

So tell me, do you have plans for Melbourne Cup Day? What are you doing? What are you wearing?

PS. More Melbourne Cup frock inspiration can be found today over at Style and Shenanigans.

* This post contains affiliate links. If you click and buy some of the items I receive a small commission – you don’t pay any extra.

Comments 42

  1. Hi hope you can give me some advise. I’m totally hopeless with colour matching so I rely on shop ladies. However my dilemma is I’m wearing a pink floral dress and bright deep pink jacket to the races and didn’t know what fascinator to wear so i went to local department store and ended up with a black and white stripe number, white clutch and white shoes(snake skin lookalikes). Am I going to look like a complete idiot as I usually do. The lady at the shop picked it out with me. There is only a small band of black on my jacket. Please help.

      1. Thankyou for the advice, it was really good. I wore a large black ring and it bought it all together. Can’t wait for next year now.

  2. Scrolling through the comments, reading that others are dreaming of getting to Flemington one day, I’ll be there! And even after 10 years going each year (either Derby Day or Oaks Day, but I will make it to the Cup one day), I still pinch myself and go “wow, I’m at Flemington”. Frock is done, shoes are oldies but goodies (made the rookie error of wearing new untried shoes once only), handbag is one of three (can’t quite decide), just have to work on my hat which I found looking unloved in a bargain bin in a vintage shop. The fashion and people watching is second to none and I believe there are some horses around too.

  3. aahh.. getting over a broken ankle so heels are out and also dresses.. wearing wide palazzo pants – top?? should I wear lacy or just a plain black and white zig zag top, no sleeves and adorn with a big red flower in the hair?? alternate is a Sandra Soulos black and white gingham blouse in memory material 3/4 sleeves, wide neckline with collar… so feeling out of it this year not wearing a dress and heels..

  4. I like the Blue Illusion fascinator Nikki and those shoes are great you’ve been showing off a few like those on everyday style – they look sexy but comfy. Love a chunky heel. At my place we are more obsessed with Halloween just now – my beastie’s daughter turns 18 that night so I bought a pair of fab angel wings for that x

  5. I am wearing the watermelon dress from this season’s @BlueI Illusion range. Yet to decide on shoes and it will definitely be a fascinator, not a hat!

  6. I read on the weekend that fascinators were over and it’s all about the perch. Which I am dead happy about because I never liked fascinators for me and I remember a fashion student friend making a perch way back in the eighties when I was in high school. I fell in love with it but have never owned one. I am actually going to go searching on Etsy and see what I can find.

  7. Those Missoni wedges are gorgeous! I always advise wearing a wedge or low heel that won’t spike the grass when at the races. Nothing like a bit of mud and turf accessorized on the heel of your shoe to add to your spring racing fashion combo! All great tips as usual Nikki. I will watch the race at home in a tee and pants most likely! It’s on my bucket list to get to Flemington one day. One can only dream. x

    1. Not to mention ruining a good pair of stilettos! Flemington is on my bucket list too – and one of the best Cup Days I had was when my eldest was a baby and I was on maternity leave. Our mum’s group all got together at one of the houses and all the bubs played on the floor while we ate and talked!

  8. Nothing for me for Melbourne Cup and that is ok, I think the last function I attended did it for me. I had ridiculously high (but ridiculously stunning) shoes on and my feet were killing me. I thought it was a sit down thing. Luckily it was at the hotel attached to Carindale and I ended up going and buying another pair of shoes to wear halfway through. I learnt my lesson and think your suggestions – especially the shoes are fabulous but still practical.

  9. Even tho’ I’m not doing anything for M-Cup day, I still had fun trying on “fascinators” in Myer the other day with mum. Wish they were fashionable to be worn every day – they’re so much fun!

  10. Great tips Nikki ,I love that orange dress I might have to pop into BigW it’s pretty.I usually dont do anything on Melbourne cup day though in the past have been to a few lunches and love watching the race and checking out all the beautiful frocks x

  11. Everything about the second outfit is stylish and very very Melbourne Cup if you are not a filly!
    This is the best time to shop for outfits in Melbourne , shop displays are gorgeous , full of flowers and fascinators.

  12. Great wrap and tips Nikki! I love anything related to Melbourne Cup and now our School Race Day is done and dusted, I’ll be joining two other families for a Melbourne Cup BBQ complete with raffles. x

  13. I’m off to a conference in Adelaide soon and the main evening event has a Melbourne Cup theme – so thanks for the advice!

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