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Henley Shirt - The Ultimate Guide

Author: Stylist at TellarDate: 2025

The henley shirt is a timeless wardrobe essential that perfectly bridges the gap between casual and elevated dressing. With its distinctive collarless design and button placket, this versatile piece has made a major comeback on fashion week runways for Spring 2025, appearing at brands like Erdem and Brandon Maxwell, proving once again that the best fashion investments are often the simplest ones.

What Makes a Henley Special?

A true henley is defined by its collarless, round neckline featuring a short button placket—typically 3-5 inches long with 2-5 buttons. Unlike a polo shirt, it lacks a collar, giving it a more relaxed, versatile aesthetic that works beautifully across seasons. Originally worn by rowers in Henley-on-Thames, this garment has evolved into one of fashion's most adaptable pieces.

How to Style Your Henley

The Casual Chic Approach

For effortless everyday style, pair a fitted henley with high-waisted skinny jeans and white trainers. I always recommend leaving the top button or two undone to create that perfectly relaxed neckline. Roll up the sleeves for an added casual touch—there's something undeniably appealing about that easy, lived-in look.

Smart-Casual Sophistication

Transform your henley into office-appropriate attire by tucking it into tailored trousers and adding a structured blazer. Choose a henley in a rich fabric like silk or fine knit for a more polished appearance. Complete with pointed-toe flats or low block heels for that perfect smart-casual balance.

Layering Mastery

Henleys excel as layering pieces. Try one under a denim jacket with joggers for an athleisure vibe, or layer beneath a chunky cardigan with ankle boots for those transitional weather days. The key is choosing the right fit—slightly fitted through the body without being restrictive.

Your Henley Shopping Guide

High Street Heroes

Zara consistently delivers on-trend henleys with contemporary fits and seasonal colours, perfect for trying new silhouettes without breaking the budget. H&M offers brilliant basics in ribbed jersey blends, including their popular fitted styles in cotton-modal combinations that feel luxurious at accessible prices.

Mango excels at elevated basics with their henley selection featuring refined cuts and quality fabrics that look far more expensive than they are. COS brings their signature minimalist aesthetic to henleys with clean lines and premium organic cotton options.

Whistles offers beautifully crafted henleys in contemporary silhouettes that work brilliantly for both casual and smart-casual occasions. Jigsaw specialises in quality knitwear, including henleys in luxurious merino wool and cotton blends with excellent drape and fit.

M&S has truly stepped up their game with henley offerings that focus on flattering fits and comfortable fabrics at fantastic value points. Their ribbed cotton versions are particular standouts.

Premium Picks

Whistles and Jigsaw bridge the gap beautifully between high street and premium, offering superior fabrics and construction. Me+Em creates investment-worthy henleys in luxurious fabrics with impeccable tailoring that justify the higher price point.

Luxury Investment Pieces

Max Mara delivers henley perfection in their signature Italian fabrics, whilst Tom Ford offers silk-cupro blends with brushed-back cotton modal for ultimate luxury. These pieces are designed to last decades whilst maintaining their shape and sophistication.

Independent Discoveries

Rapanui Clothing creates sustainable henleys from organic and recycled materials in their renewable energy-powered factory on the Isle of Wight, proving that ethical fashion doesn't compromise on style or quality.

Community Clothing, founded by Patrick Grant, produces beautiful henleys entirely in the UK using traditional manufacturing techniques, supporting local communities whilst creating pieces that celebrate British craftsmanship.

The Perfect Fit

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Your henley should skim your body without being tight or baggy. The shoulder seams should sit precisely on your shoulder points, and the hem should fall just at your hip bone. For layering, choose a slightly more fitted style; for wearing solo, you can go for a more relaxed cut. The neckline should sit comfortably without gaping when buttoned.

Fabric and Care

Cotton remains the gold standard for henleys, offering breathability and improving with age. Cotton-modal blends provide added softness and drape, whilst cotton-cashmere combinations offer luxurious feel for investment pieces. Always check care labels, but most cotton henleys are wonderfully low-maintenance—machine washable and tumble-dry friendly.

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The Bottom Line

The henley shirt deserves a place in every thoughtful wardrobe. It's the piece that works when you want something more elevated than a t-shirt but less formal than a blouse. With the right fit and styling knowledge, your henley will become that reliable piece you reach for again and again. Whether you're investing in a luxury piece or building your basics collection with high street finds, choose quality over quantity—a well-made henley will serve you beautifully for years to come.

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