5 Days, 5 Ways: The Check Shirt

5 Days, 5 Ways: The Check Shirt

Ch-ch-ch-ch-ch-check it out
check shirt, charles tyrwhitt

By Gabi Meyers | Last Updated: Jun 23 2022 | 2 min read

A solid wardrobe consists of at least a handful of patterns. Your very first button up shirt was probably a solid white, followed by a French blue, and then maybe a gingham number…but have you checked out checks? A check shirt gives a quiet but impactful dose of visual interest, and never goes out of style.


check, shirt, charles tyrwhitt, check shirt


The check shirt is an easy option to add a touch of visual interest to any outfit.

suit, navy, pink tie, watch, check shirt

Suit: Suit Supply, $999 | Tie: The Tie Bar, $19 Watch: Michael Kors, $250

Shoes: Johnston & Murphy, $155 | Belt: Bonobos, $98 | Glasses: Warby Parker, $95

Wear it well: Take pattern play to the next level by pairing your check shirt with a dotted tie.


green pants, blazer, check shirt, sportscoat, trousers, hopsack, cole haan, acne

Blazer: Gant, $650 | Pants: Acne Studios, $240 | Tie: Frank + Oak, $26

Oxfords: Cole Haan, $270 | Work Bag: Mismo, $550 

Wear it well: Add some fun to your weekday work look by skipping the socks and flashing that ankle.


red pants, retrosuperfuture, carhartt wip, check shirt, charles tyrwhitt, paul smith, jack purcell, converse, publish

Bomber: Your Neighbors, $89 | Chinos: Incotex, $295 | Sneakers: Converse, $125

Sunglasses: Carhartt WIP, $218 | Cap: Publish, $44 | Wallet: Paul Smith, $150

Wear it well: Match your pants to your favorite accent color in the check, and balance the loud pants with all black everything else.


going out outfit, check shirt, thursday night, coach jacket, embroidery, paul smith, red ear, made and crafted, levis, tom ford
Paul Smith Red Ear, $525 | Jeans: Levi’s Made & Crafted, $160 Cologne: Tom Ford, $220

Sneakers: Onitsuka Tiger, $70 | Key Holder: Areaware, $56 | Wallet: Jack Spade, $88

Wear it well: Go mostly monochrome by dressing around one accent color in the check pattern.


shorts, sweatshirt, check shirt, sunglasses, bass, steven alan, miansai, herschel, saturdays

Sweatshirt: Saturdays NYC, $120 | Shorts: Fred Perry, $125

Penny Loafers: G.H. Bass & Co., $110 | Sunglasses: Steven Alan Optical, $165

Bracelet: Miansai, $85 | Backpack: Herschel Supply Co., $60

Wear it well: Skip the office and pair your work top with your weekend favorites for a Friday in the park.



Want to see more ways to wear the items featured in this article? See 5 ways to wear a crewneck sweatshirt, statement bomber and minimal sneaker.

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.