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Black Friday Early Access | 35% Off Everything

Black Friday Early Access: Offer valid 11/6/2026 at 12:00 AM ET through 11/18/2026 at 11:59 PM ET, valid online and in-stores. To redeem online, enter code EARLY at checkout.

Cannot be combined with any offers or promotions. Offer has no cash value and is not valid on previous purchases, or purchases of gift cards. Exclusions may apply. See full return and exchange details here.

Black Friday Early Access | 35% Off Everything

Black Friday Early Access: Offer valid 11/6/2026 at 12:00 AM ET through 11/18/2026 at 11:59 PM ET, valid online and in-stores. To redeem online, enter code EARLY at checkout.

Cannot be combined with any offers or promotions. Offer has no cash value and is not valid on previous purchases, or purchases of gift cards. Exclusions may apply. See full return and exchange details here.

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Wrinkle-Free Caldwell Shirt

  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
    New
  • Wrinkle-Free Caldwell Shirt
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Wrinkle-Free Caldwell Shirt
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Model is wearing UNTUCKit Caldwell wrinkle-free plaid shirt in red.
  • Video of a model wearing an UNTUCKit Wrinkle-Free Shirt

Wrinkle-Free Caldwell Shirt

$115.00

35% Off with Code EARLY

Color White & Red Plaid
Size
Fit
Make it personal—add a gift note at checkout.

Ditch your iron and make the most of the season. This Wrinkle-Free button-down comes out of the dryer crease-free and ready to wear, so you can spend less time getting ready and more time out the door. It combines fine shirt details, including a polished button-down collar, single-needle side seams, and structured cuffs, with the comfort of an untucked shirt.

Red and white plaid practically signals the holidays, so it's a natural pick for the office party or a cozy get-together with the neighbors. Layer a sweater over it when the temperature drops, and the plaid peeks out at the collar just right. Pair it with our 5-Pocket Chino Pants or your favorite jeans for an easy cold-weather look.

It has the perfect untucked length, a chest pocket, and our signature red sail at the hem.

FEATURES

● Button-down collar
● Chest pocket
● Red signature sail
● Perfect untucked length
● SKU #41939RED

FABRICS

● 100% Cotton
● Imported

Regular Fit - Our classic cut with the perfect untucked length. Runs slightly smaller than traditional shirts. 

Slim Fit - Two inches less fabric in the body and a half inch less in the sleeve.

Relaxed Fit - Three extra inches of room in the body without any extra length.

Regular Tall Fit - This fit has two extra inches of length in the body and sleeves.

Slim Tall Fit - Two inches slimmer in the body and one inch slimmer in the sleeve—plus two inches of length in the hem and sleeves.

Machine wash cold with like colors

Do not bleach

Tumble dry

Medium heat

Remove promptly

Iron warm, if needed

NO DRY CLEANING NECESSARY

Free Shipping on orders $110+. Free Returns online and at 80+ stores within the US.

Overall rating: 4.4166665 / 5 from 12 reviews.

AI Generated Review Summary

Summary topics

Review topics: [fit, quality, pattern, shirt, difference, wife, button, wrinkles, print].

Review highlights

Reviews

Comfortable

"Comfortable"

— Matthew A. (5/5)

No Longer a Fan

"Your shirts are not the quality and fit I loved for years. This shirt is too long and fits tight in the shoulders. I have tried your relaxed fit but it is more for portly guys with bellies. You really need an athletic fit for us guys who lift. Being larger in your upper body does not necessarily mean you also have a gut. Would have returned but washed before wearing."

— Anonymous (1/5)

My Caldwell Wrinkle Free Shirts

"These shirts are amazing. Even the buttons and button holes are superior quality You can immediately tell the difference."

— Robert S. (5/5)

Continue to be my go-to for shirts

"I love the quality of the shirt, size and fit options, and especially the untucked length (thus the name - UNTUCKit). Have bought many of their offerings and will continue to buy more."

— RICHARD E. (5/5)

Wrinkle free Caldwell shirts

"My son loved the shirts, he is wearing them to work and they are very comfortable and nice looking! No wrinkles!!"

— Susan K. (5/5)

My Wrinkle Free Caldwell Shirts

"These shirts are totally amazing. Even the buttons and button holes are noticeably better"

— Robert S. (5/5)

Wrinkle free Caldwell shirts

"My son loved the shirts he is wearing them to work and they are very comfortable and nice looking! No wrinkles!!"

— Susan K. (5/5)

Wrinkle feee Caldwell shirt

"Nice quality and looks nice and wears well. No wrinkles."

— Susan K. (5/5)

Wrinkle-Free Caldwell Shirt

"Great print and another shirt added to the collection."

— Dwayne C. (4/5)

Wrinkle-Free Caldwell Shirt

"Great pattern and wife loves the way it looks"

— Dwayne C. (4/5)

Q&A