Nothing in this piece is sponsored. The apps and platforms mentioned are simply the ones I would point a friend towards. One of them is ours. Enclosure dress codes vary by racecourse and by enclosure — always check the official guidance for the ticket you hold rather than taking a blog's word for it, including mine.
What actually wins Best Dressed
I have stood on the lawn at Doncaster with a clipboard, and I can tell you the thing that surprises people most: the winner is almost never the person wearing the most expensive outfit. Judges are not valuing your wardrobe. We are looking at whether the whole thing hangs together, and whether you look like you are enjoying it.
What we notice, in roughly this order:
- Whether the colours belong to you. A woman in a shade that lifts her face will beat a woman in this season's colour every time. It reads as confidence, but it is really just the right palette.
- Proportion. Hem, heel and hat brim in conversation with each other. Get those three right and the outfit looks designed rather than assembled.
- One clear idea. The best looks say a single thing loudly. Two competing ideas — bold print and a statement hat and a bright bag — cancel out.
- The finish. Bag, shoes, a good coat over the arm in case. This is the part people skip, and it is the part that separates the top ten from the top three.
- Joy, honestly. You can see it from twenty feet. Someone who feels wonderful in what they are wearing photographs differently from someone enduring their shoes.
None of that requires anything new. Every single one of those points is achievable from a wardrobe you already own — which is the reason I can write this piece with a straight face.
250 years on the Town Moor
I say this as someone who grew up near that moor: the St Leger is not a borrowed occasion for Doncaster. It is ours, it is older than almost everything around it, and Ladies Day is the day the town dresses up. That matters to how you approach the outfit. This is not a fashion week audition. It is a local tradition with two and a half centuries behind it, and there is something rather lovely about turning up in something with a history of its own.
How to look the part — sustainably
What follows is not a trend forecast. Chasing this season's look means buying this season's clothes, which is the opposite of the point. These are the principles I work to as a designer, and the ones I find myself rewarding as a judge — and unlike trends, they hold from one year to the next.
1 · Start from what suits you, not what's trending
Your colouring lasts a lifetime. A trend lasts a season. The women who place well are almost always in shades and shapes that genuinely work for them, which is why they look at ease rather than costumed.
How: find your colour season with our free colour quiz, then go through what you already own looking for the strongest thing in that palette. Build the outfit in Remix Studio as a flat lay so you can see it before you commit. Our body shape guide covers the proportion side — information, not instruction.
2 · Choose pieces with a second life
The single most useful question before any occasion purchase: where else does this go? A dress that works for a wedding, a christening and a good dinner is worth five times one that only works on a lawn in September.
How: if the honest answer is nowhere, do not buy it — rent it and send it back. One-wear buys are the worst value in any wardrobe and the easiest thing to stop doing.
3 · Let accessories carry the drama
This is the whole trick, and it is the sustainable one. A plain base you already own plus one remarkable accessory reads as an occasion outfit. The reverse — an elaborate dress with nothing on your head — reads as a nice dress.
How: put the money and the interest into the hat, the bag or the shoes. All three are the easiest things in fashion to find pre-loved, because they barely wear out.
4 · Invest in a hat, not a haul
A well-made hat is the most renewable thing you can own. A base can be re-blocked, re-trimmed and re-coloured and worn for a decade, looking different each time. Nobody remembers last year's trimmings.
How: one good piece, cared for and refreshed, beats a new fascinator every season — and costs less over its life. A charity-shop base you re-trim yourself is better still.
5 · Confidence over newness
I will say it plainly, having judged it: the best-dressed are rarely the newest-dressed. Fit, colour and how you carry the thing beat a brand-new outfit every time, and they are visible from across the lawn.
How: wear it in beforehand. Walk in the shoes. Check the hat stays put in wind. Comfort is what confidence is actually made of.
Building the outfit, in order
Four steps, deliberately ordered. Each one means less has to be made than the step below it, and most people never need to get past the second.
1 · Start with what you own
Nearly every race-day outfit I have ever judged could have been assembled from a wardrobe that already existed. The problem is not a shortage of clothes — it is that nobody has put them together yet.
This is precisely what we built Closet Remix for. Open the Remix Studio and lay out a look as a flat lay: dress, jacket, shoes, bag, hat, moved around until it works. Use your colour palette so you are choosing shades that genuinely suit you rather than shades that are merely fashionable. Check the shapes that work for you — our body shape guide covers how that reading is done, and why it is information rather than instruction.
Do this a fortnight before, not the night before. You will find gaps while there is still time to fill them properly, and you will usually find you have more options than you thought.
2 · Rent the hero piece
If there is one thing you genuinely do not own — the dress, the coat, the statement piece — rent it rather than buy it. Occasion wear is the worst value in any wardrobe: highest cost, fewest wears. It is the clearest case in fashion for not owning at all. HURR and By Rotation are the two UK platforms I would look at first.
3 · Buy pre-loved
Vinted and Depop are full of occasion dresses worn once — which is the whole tragedy of race-day fashion, and also its opportunity. Someone else's single-wear dress at a fraction of retail, and nothing new made. Search by colour rather than by brand and you will do better.
4 · Charity shops for the finishing touches
Doncaster's charity shops are genuinely good, and accessories are where they are unbeatable. Bags, shoes, brooches, hats, fascinators — the small things that finish a look and that nobody needs new. I have found hat bases for a couple of pounds that I have re-trimmed and worn for years.
And when the day is done, take the things you will not wear again back. That is the loop working as it should.
If you do end up buying something new, buy it from someone doing it properly — our brand directory lists more than sixty brands worth the money, each one researched.
Hats & fascinators
Not my specialism — I have made exactly one and designed another — but I judge them every year, and headwear is the single most efficient thing you can do to an outfit. A plain dress plus a remarkable hat is an occasion look; a remarkable dress plus no hat is a nice dress.
It is also, counter-intuitively, the most sustainable part of the whole outfit — because a hat is endlessly renewable. A base can be re-blocked, re-trimmed, re-coloured and worn for a decade under different guises. Nobody remembers a hat's trimmings from three years ago. Change the flowers and it is a new hat.
If you are starting from nothing, in order of what I would actually do: borrow one from a friend who has a good one, buy a plain base from a charity shop and trim it yourself, or rent. Buying a new fascinator to wear once is the least interesting option available to you.
On whether you must wear one — headwear is expected in the premier enclosures at most courses and encouraged elsewhere, but codes differ, so check yours. My advice is to wear one regardless. Ladies Day is one of the few remaining days in British life where a hat is entirely normal. Use it.
The point of dressing up
There is a version of sustainable fashion that sounds like a telling-off, and I have no interest in it. Getting dressed up is a joy. The morning of Ladies Day, the whole town in its finery, someone's fascinator going sideways in the wind on the Town Moor — that is not something to feel guilty about.
The point was never to dress down. It is that the most striking outfit on the lawn is usually the one with the most thought in it, and thought is free. The clothes are already here. Two hundred and fifty years of this race have happened without anybody needing a new dress to enjoy it.
So build the look, wear it, and wear it again. If you want a number to make that feel good rather than frugal, run the dress through our rewear calculator and watch the cost per wear fall every time you put it on. And if you want to get better at this generally, the capsule guide is the same thinking applied to the other fifty-one weeks of the year.
Common questions
What should I wear to the races?
Something you feel wonderful in, that suits the weather and lets you stand up for six hours. Beyond that, most meetings expect smart daywear — a dress, or tailored trousers or a skirt with a jacket — and Ladies Day is the one where hats and fascinators come out properly. Enclosure codes differ between racecourses and between enclosures at the same course, so always check the official guidance for the enclosure on your ticket before you plan the outfit.
Do I have to wear a hat to Ladies Day?
At most meetings headwear is encouraged rather than compulsory in the general enclosures, and expected in the premier ones. Check your racecourse. But I would say wear one anyway — Ladies Day is one of the few days left in British life when a hat is entirely normal, and it is the quickest way to make an outfit you already own look like an occasion.
How do I put together a race-day outfit without buying anything new?
Start with your own wardrobe — most race-day outfits are already hiding in one, they just have not been put together yet. Then rent the hero piece if you need one, buy pre-loved for a dress or bag, and use charity shops for the finishing touches. In that order, because each step means less has to be made.
When is St Leger Ladies Day 2026?
Ladies Day falls on Thursday 10 September 2026, within the Betfred St Leger Festival — the meeting that in 2026 marks 250 years of the St Leger Stakes. Confirm the day and the enclosure details on the Doncaster Racecourse website before booking, as festival schedules can change.
Is it acceptable to wear the same race-day outfit twice?
Yes, and it is rather the point. A good occasion outfit should earn its keep. Change the hat, change the shoes, change the jacket and nobody is counting — and if you are logging wears, watching the cost per wear fall on a dress you love is far more satisfying than buying a new one nobody has seen.
Festival dates and dress codes are given in good faith from the racecourse's published information at the time of writing. Always confirm the current details at doncaster-racecourse.co.uk before booking or planning your outfit.