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Mizzen+Main/Twillory
Whether you're dressing for the office daily or a one-time special occasion, wearing one of the best wrinkle-free dress shirts for men is a sure way to stay comfortable all day long. Also known as performance dress shirts, these shirts feature stretchy, breathable materials that will keep you cool, sweat-free, and wrinkle-free. On top of being easy to wear, most of the best wrinkle-free dress shirts are easy to maintain, as they are machine washable.
Our top pick is the Mizzen + Main Leeward Dress Shirt because of its consistent moisture-wicking fabric and a vast array of color options. If you're looking for something more budget-friendly, Twillory's shirts can be had for as low as $79 each when bundled.
This Mizzen + Main dress shirt really has it all, from moisture-wicking fabric to four-way stretch to an astonishing array of colors. Select from two fit and two length options, and feel confident about its anti-microbial technology, too.
Best budget: Twillory
Twillory
Twillory shirts are well worth it at full price, but the deal gets even better when you bundle — and if you're shopping for a workwear wardrobe, you'll likely want more than one color or pattern anyway.
Typically priced at $99 each, they can be as cheap as $79 each when you buy four or more. And for shirts that feature four-way stretch and a non-iron wrinkle-free material, that's hard to beat.
Best machine-washable: Bonobos
Bonobos
Bonobos is a brand seemingly never at rest when it comes to innovation, be it the company's game-changing chinos or its well-executed performance dress shirt. The wrinkle-resistant, moisture-wicking fabric delivers an activewear feel with the crisp look of a dress shirt, but the real key is that this shirt stands up more than adequately to repeated machine washing.
Best temperature-regulating: Ministry of Supply
Ministry of Supply
Ministry of Supply doesn't cut corners when it comes to the best performance dress shirts on the market. Case in point: The fact that this stylish dress shirt is built with NASA-grade temperature regulation and an absurdly breathable, lightweight, and sweat-wicking pique knit fabric. The brand claims it's 19 times more breathable than cotton, and our wear tests seem to back that up. As an added bonus, it's machine washable.
Best short sleeve: Untuckit
Untuckit
There are times — say, on Casual Friday — when a long-sleeve dress shirt is going to feel a little too formal. Ditch the excess fabric in a way that's still dressy with a stretchy performance shirt in a short-sleeve cut from Untuckit, and feel confident about your #OOTD knowing that this shirt is made to be worn, well, untucked. It's also flexible enough to wear with everything from shorts to chinos.
Best stretch: Rhone
Rhone
Searching for the feel of a workout shirt with the polish of a dress shirt? It's a tricky formula to perfect, but Rhone gets it right with the aptly named Commuter Dress Shirt. It's ideal for staying cool and comfortable (yet refined) on the go, whether your plans take you through the city to a rooftop happy hour or across the country for a coastal wedding. Crucially, it's built with 4-way stretch and anti-odor technology.
Best for inclusive sizing: Swet Tailor
Swet Tailor
Polished performance is the name of the game with Swet Tailor, which delivers a substantial range of size options and builds its shirts with bigger guys in mind. The shirt blends a tailored look with a cotton-spandex blend for crucial stretch and breathability. Better still is the fact that this shirt can be worn tucked or untucked, and any of the versatile, breezy color options should match other classic wardrobe colors.
Best slim-fit: Ash & Erie
Ash and Erie
A slim-fit dress shirt can add plenty of polish to your wardrobe, whether worn tucked in with the sleeves rolled up or paired with a well-fitting sweater or cardigan. Here, Ash & Erie makes it easy to find your perfect fit by neck sizing, and two reliable colors deliver plenty of styling potential in any season. For good measure, the wrinkle-resistant cotton is an optimal touch for tailored occasions aplenty. These shirts are also ideal for shorter guys (5'8" and under).
Best Oxford: Western Rise
Western Rise
It's not often you come across a dress shirt that can perform as readily out in the field as it can back at the office or at a rooftop happy hour, but Western Rise has somehow managed to do the impossible. The key is the use of moisture-wicking, anti-microbial merino wool. What really seals the deal in terms of wearability is the expertly designed, hidden Oxford button-down collar – that makes this one of the best performance dress shirts you can actually wear with dark blue jeans as well as tailored wool trousers or stretch cargo chinos.
Best formal: Eton
Eton
For formal affairs — everything from a black tie to an all-important business meeting — a dress shirt with a more dressy flair is more than acceptable. In fact, it's practically required, and Eton dress shirts rise to the occasion. The elastane-enhanced recycled yarn is plenty stretchy, but it's the cutaway collar that takes this performance-minded shirt to the next level.
Best made-to-measure: Woodies Clothing
Woodies Clothing
Buying one of the best performance dress shirts doesn't have to feel intimidating – it can be as easy as taking your measurements (a fairly simple process) and then selecting from a wide array of options via Woodies. The results are tailored to your liking, from the collar to the cuff design, and you can even add a monogram.