What to Wear to a Day at the Races in 2027

What to Wear

The core pieces for a day at the races in 2027 include a tailored blazer or structured dress as the foundation, paired with trousers or a midi skirt for women, or chino pants or tailored shorts for men. A wide-brimmed hat or fascinator is essential for women, while men should opt for a fedora or panama hat depending on the dress code. Footwear should be block-heeled pumps or loafers—think brands like Cole Haan for comfort or Mango for affordable elegance. The palette leans toward soft pastels (lavender, blush, mint) and neutrals (cream, navy, taupe), with accent colors like coral or emerald for pops of personality. Real brands that fit this look include Aritzia for women’s blazers and Bonobos for men’s tailored shorts.

For Men

Masculine-presenting women — these looks work for you too.

Here are three outfit boards for men, tailored to the 20s, 40s, and 60s age bands, each reflecting the appropriate level of formality and trend awareness.

For Women

Feminine-presenting men — these looks work for you too.

Here are three outfit boards for women, covering the 20s, 40s, and 60s age bands, with pieces that balance trend, tradition, and comfort.

How to Adapt by Age

As you move from your 20s to your 60s, the key shift is from trend-driven pieces to timeless classics. In your 20s, you can experiment with bold patterns, shorter hemlines, and unstructured blazers, while in your 40s, focus on tailored fits and neutral palettes with subtle accents. By your 60s, prioritize luxurious fabrics like wool, silk, and lace, and opt for structured silhouettes and elegant accessories like a fedora or pearl jewelry to maintain a refined, age-appropriate look.

Common Mistakes to Avoid

• Wearing denim or sneakers – This is a formal occasion; jeans and athletic shoes are not acceptable, even in the 20s age band.
• Choosing an overly large hat – A hat should complement your outfit, not block the view of those behind you; keep brims under 6 inches.
• Ignoring the weather – Races are often outdoors; bring a light trench coat or pashmina for sudden rain or wind, not a bulky jacket.
• Over-accessorizing – Stick to one statement piece (hat, necklace, or pocket square) and keep other accessories minimal to avoid a cluttered look.
• Forgetting comfortable footwear – You’ll be on your feet for hours; avoid stilettos or thin soles, and opt for block heels or loafers from brands like Cole Haan for all-day comfort.

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FAQ

Can I wear a jumpsuit to the races? Yes, a tailored jumpsuit in a solid color like navy or blush can be a stylish alternative to a dress, especially for women in their 20s or 40s. Pair it with a belt and statement earrings to elevate the look.

What color should my hat be? Your hat should complement your outfit, not match it exactly. For example, a cream hat works with a navy dress, while a taupe hat pairs well with pastels. Avoid black hats for daytime events.

Are open-toe shoes acceptable for men? No, men should stick to closed-toe shoes like loafers, brogues, or oxfords. Open-toe sandals are too casual for the races, even in warm weather.

How formal should the outfit be for the Royal Enclosure? For the Royal Enclosure, women must wear a hat or fascinator and a dress or skirt of knee-length or longer. Men need a suit and tie, with a jacket worn at all times. Avoid shorts or bare legs.

Can I wear a fascinator instead of a hat? Yes, fascinators are acceptable for women, especially in the 20s and 40s age bands. Ensure it is secure and proportionate to your face shape—avoid oversized designs that may fall off.

Bottom Line

Dressing for a day at the races in 2027 is about combining tradition with personal style—choose a tailored blazer or structured dress in a light palette, add a hat or fascinator for women, and finish with comfortable yet elegant shoes like loafers or block heels. Avoid casual items like denim or sneakers, and adapt your look by age, with younger wearers embracing trends and older ones focusing on timeless elegance. With these boards, you’ll be ready for the paddock, the grandstand, or the Royal Enclosure.

*Published June 2027 · Updated June 2027*