Ascot season is here, and whether you've had your invite stuck on the fridge since January or you’ve only just started mentally preparing for what to wear to Ascot (no judgement), now is the time to get your outfit in order. The event itself may centre around racing, but let's be honest: fashion is just as much a part of the spectacle. From oversized hats to elegantly tailored dresses, Ascot has always been about showing up and showing out—albeit with a few rules to follow.
If you're anything like me, the words "Ascot dress code" might conjure up images of overly prim outfits, stiff fascinators, and a slightly overwhelming list of dos and don'ts. But the reality is, Ascot dressing has evolved. While there are still official guidelines—particularly for certain enclosures—the modern approach to race-day fashion is far more creative than you might expect. It's less about fitting into a rigid mould and more about expressing your personal style within the parameters. You'll still want a hat for some outfits (or at least a very good headpiece), but gone are the days of cookie-cutter occasionwear. Now, there's room for bold colours, directional tailoring, and even a flat shoe if you style it right.
That's not to say it has to cost a fortune, either. As much as the races are a natural home for British designers like Emilia Wickstead and Erdem, I've found some of the most head-turning race-day looks come from the high street. A great blazer and midi skirt from & Other Stories, paired with a strong accessory moment from Missoma, can look just as elevated as any runway look—especially when styled with confidence. Pieces like the poplin midi skirt, the new wave of minimal clutches and slingback sandals have a certain Ascot energy without veering into costume. In short, looking the part is far more achievable than you might think. And It’s all proof that classic event dressing is still very much in fashion—but with fresh energy and modern proportions.
And let's not forget those pop culture fashion moments that live rent-free in our minds. I always think of My Fair Lady, not just for the (admittedly over-the-top) Ascot scene, but for the transformation that clothes offer. It's that same thrill you get when slipping into something with a bit of drama, even if it’s just a perfectly cut blazer or a head-turning earring. You don't need a Hollywood budget to create that feeling.
So, if you're wondering what to wear to Ascot this year, scroll on. These outfit ideas combine everything I love about this particular corner of the fashion calendar: playful styling, heritage references, and pieces that work hard well beyond race day.
Shop Our Favourite Ascot Outfits:
1. Black Dress + Mules + Clutch Bag
Style Notes: There's something about a black dress at Ascot that feels quietly confident. It's the opposite of try-hard—sleek, classic, and surprisingly versatile. While lighter colours dominate race-day dressing, black brings a refined minimalism that instantly stands out. Pair it with some trendy mules (the kind that starts conversations) and a clutch for balance. Bonus points if the dress has interesting details like an open back or asymmetric hem—those subtle twists are what elevate the look.
Shop the Look:
A quietly luxe take on eventwear.
Love a mule moment.
Black raffia design and plenty of room for your phone, lipstick and keys. This ticks all the boxes.
Simply stunning.
2. Blazer + Poplin Skirt + Block Heels
Style Notes: This is the kind of outfit that's perfect for transitional weather and anyone who doesn't want to feel overdressed. A blazer instantly sharpens up a floaty poplin skirt, and the contrast in structure makes the outfit feel thoughtfully styled. Block-heeled sandals add comfort without compromising on height, which is especially useful when navigating grassy enclosures. If you love a low-key tailored moment, this is your route.
Shop the Look:
This blazer has a waisted cut that is very much In right now.
An elevated basic. This one has volume without bulk and is cut from crisp cotton that holds its shape. It also has pockets—which, frankly, should be mandatory.
Low-maintenance glamour. These have a retro feel and come in multiple shades, but the creamy nude version is especially good with pastels and soft tailoring.
Who doesn't love a fascinator moment?
The bag of dreams—well done The Row.
This silver cuff brings in a hint of polish while still keeping the look directional.
3. Floral Dress + Wedge Sandals + Top Handle Bag
Style Notes: Florals for Ascot? Predictable, yes. But done right, they still work. The key is to opt for either a bold oversized print or a hyper-feminine shape to give it personality. A chic wedge sandal (which we saw a lot of at Chloe this season) gives that extra summer push. Add a structured top-handle bag to balance the softness.
Shop the Look:
Zimmermann has become a go-to for event dressing, and this floral silhouette is one of its most flattering.
Super chic and comfortable—win, win.
Sleek, sculptural and surprisingly roomy. It's not Ascot without at least one Aspinal piece.
The shape is somewhere between sunhat and fedora—perfect for a less traditional look.
I meant, why not.
Love.
4. Off-the-Shoulder Two-Tone Dress + Ballet Flats
Style Notes: For those who like their occasionwear to feel a little less traditional—but no less refined—an off-the-shoulder dress offers that perfect balance. It's romantic without being saccharine, and when done in a modern two-tone palette, it makes just the right kind of statement. Ballet flats give this outfit a grounded feel and offer some very welcome comfort if you're on your feet all day.
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I gasped when I saw this dress.
A classic shoe.
Toteme you win me over every season.
Simple, sculptural and perfect for those who don't want to over-accessorise. They catch the light in photos too, which is always a bonus.
This choker works especially well with the off the shoulder dress.
5. Pink Pantsuit + Pumps + White Bag
Style Notes: The pink suit has officially graduated from trend to staple, thanks to consistent appearances at Valentino and Chanel. It's playful, powerful and surprisingly easy to wear—especially when styled with tonal accessories. A white top handle mini bag lends a softer, summery contrast, and white pumps help keep the look from veering too corporate.
Shop the Look:
Jigsaw does tailoring incredibly well, and this blush pink blazer feels both modern and wearable.
The trousers come in petite and tall options too.
These are genuinely comfortable (I own them in black), and the heel elongate the legs, especially with cropped trousers.
A mini bag that is anything but useless.
The delicate detailing is what sold me.
A delicate bracelet always finishes off a tailored look.
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