Women's Designer Fashion & Luxury Clothing | ME+EM
Woman stood in front of a concrete wall in a long white dress with a white jumper tied around her waist.

What to Wear To Henley Royal Regatta

25 June 2026

Words by: Esther Achara. Design by: Melanie Makariou.

Even though you're heading to the UK to support your US team of choice—Harvard! Yale! MIT!—think of your approach to dressing as you would a typical US event: a little formal, a little relaxed, but always polished (unless you’re heading to The Stewards Enclosure or Hospitality Tent, where dresses should be below the knee and you’d ideally wear a hat). Henley guests are also magnetically attracted to all-things preppy, for obvious reasons, and with unreliable weather in Oxfordshire during July, throwing a blazer in your suitcase will solve two problems at once.

Whether prints, texture, or monochrome outfits harbour most appeal, we've compiled six options ahead—from floral dresses and blazers to tailored shorts and polo shirts with flats, or solid block heels for navigating grassy terrain—that nod to the event's collegiate vibe without ever veering into cosplay.

A Floral Dress & Blazer

This one is less about the florals and more about the strategic ruching at the midsection. With its high neck and fluid outline, that hugs in all the right places, it’s a lengthening, streamlining dream. The contrast piping offers a modern and individual touch that you’ll want to reach for repeatedly. Add the prerequisite touch of prep with the oversized icon blazer in navy and pair with an off-white handbag.

A Polo Shirt & Tailored Shorts

If you’d rather lean more on the casual side, stick to a pair of preppy shorts and a polo shirt (while the sport isn’t accurate the vibe is spot on) and add a snakeprint belt to tie it all together. A little elevation with some kitten heeled sandals will stop it from feeling too relaxed and add a little femininity to an otherwise masculine-inspired look.

A Textural Dress & Blazer

A dress is always a good idea and if finding one that stands out in a sea of florals is your MO, then a textural, crochet-style lace option is a good direction to head in. While the woven pattern reflects a floral, it’s more graphic and interesting than many on the market. Lined with a slip and designed with a back split for ease of movement, it’s the type of dress that does all the work and leaves you feeling polished and comfortable.

A Subdued Matching Set & Necktie

A matching top and skirt that reads as a dress is one of the most useful closet additions you can invest in. Worn together, they convey an air of elevation but broken down and worn with denim (a jacket in the skirts case, jeans in the top’s) they’ll be on almost constant rotation. For something like Henley, it’s the perfect summery look, particularly if florals aren’t your thing. Add a preppy touch with a chic, silk necktie, worn loosely around your neck and draping down, either the front or back of your look. Pair with caged heels to ramp up the polish, and retro sunnies that nod to the late 70s/early 80s vibe.

A Retro Tailored Jumpsuit

Should you crave something different to a dress but more polished than shorts, a jumpsuit might just fill the gap. This linen-blend 70s-feel option, with darted seams and softly pleated legs, creates a streamlined effect. Wear the buckle as is or switch for one in a contrasting hue. A pair of flats, like these V-cut peep-toes, are the perfect modern complement, while a clean clutch won't compete with the jumpsuit's retro drama.

A Monochrome Dress & Scarf

White in summer is something of a classic, and this cotton poplin maxi, made from comfortable stretch fabric, handles the look with modern elegance. Contrast it with warm earthy brown accessories: a crossbody bag, flat printed shoes and dotted scarf. Worn around your neck, waist, or in your hair, it adds an uplifting touch that makes the whole look sing.

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