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10 Best Dress Shirts Under $50 for Men on Amazon

With the temperatures starting to dip and the holidays coming up, it’s time to swap out that tee you’ve been wearing all summer and change into something that will make you look and feel a little bit more polished. You might not be wearing a dress shirt as often as you were in the pre-COVID days, but that doesn’t mean there aren’t any opportunities to get dressed up. Since our social calendars aren’t too full, anytime we have a gathering calls for a step-up in the style game.

Without dishing out hundreds, you can find dress shirts that are comfortable (from the best men’s clothing brands) and breathable, which is really all that anyone wants when it comes to putting on a fitted shirt. Gain some major style points with these affordable menswear options from some of the best men’s brands on Amazon Fashion:

Chef Works Men’s Gingham Dress Shirt

Whether you’re throwing this dress shirt on with boxer briefs for a last minute Zoom meeting or you have your first date in what seems like years, this dress shirt will instantly make you look polished.

Dockers Men’s Long Sleeve Signature Comfort Flex Shirt

Sure, you probably have a white dress shirt in your closet, but do you have one that is machine washable, doesn’t wrinkle and has stretch to it? No? Exactly, that’s what we thought. Add to cart immediately.

COOFANDY Men’s Casual Dress Shirt Button Down Shirts Long-Sleeve Denim Work Shirt

This fashionable soft denim dress shirt is perfect for an occasion when you’re not sure if you should be dressing up or dressing down. We love the contrast from the plaid cuffs and buttons that instantly elevate this dress shirt.

Tommy Hilfiger Men’s Dress Shirt Slim Fit Non-Iron Gingham

Remember that time you tried hanging your dress shirt in the bathroom to get the wrinkles out, but really it just got wet? No need to worry with this shirt. The non-iron fabric resists wrinkles so you’ll look crisp all day long.

Unlisted by Kenneth Cole Men’s Dress Shirt Slim Fit Checks and Stripes

If you want to show off your figure, try a slim fit dress shirt that will hug your body and compliment all of the work that you put in during quarantine.

Nick Graham Men’s Modern Fitted Multi Gingham Stretch Shirt with Solid Tie

Gone are the days of trying to figure outfit your tie clashes with your shirt. This dress shirt and solid tie set takes all of the guess work out for you.

Amazon Essentials Men’s Regular-Fit Long-Sleeve Plaid Casual Poplin Shirt


If most of your dress shirts in your closet consist of different variations of the colors blue and white, it’s time to kick it up a notch. Since you’re probably not wearing dress shirts on the regular, step out of your comfort zone and try a bold color combination. Blue and orange is unexpected but still super stylish.

Van Heusen Men’s Flex Long Sleeve Button Down Stretch Plaid Shirt

Nothing screams “perfect fall dress shirt” quite like this shirt. With the softness and vibe of a flannel shirt, without the heaviness and warmth, this top is perfect for when you want to step it up, but still look cool and casual. If your significant other is requesting a day at the wineries or pumpkin picking, this shirt is perfect.

Kenneth Cole REACTION Men’s Dress Shirt Slim Fit Technicole Stretch Solid


If all black is your aesthetic, we’ve found you the perfect shirt. This dress shirt is extremely comfortable and looks great paired with slacks or dark denim. The best part? If you’re sipping on red wine this holiday season and accidentally bump into the charcuterie board, you don’t have to worry about any stains.

IZOD Men’s Big and Tall Button Down Long Sleeve Stretch Performance Plaid Shirt

If slim fit isn’t your style, we’re here to make dress shirt shopping less of a nightmare. With plenty of room and stretch through the chest and arms, you’ll no longer feel restricted and uncomfortable when you have to get dressed up.

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