I love revisiting my closet staples with fresh eyes and discovering new ways to style them for another season. Today I’m doing exactly that and sharing four ways to consider styling a basic white button up.

I’ve had The Tailor Proper Fit shirt by Power of My People in my closet since the start of 2021 and it only seems to get more comfortable and more versatile with every season.

I love the crisp white, single pocket, tonal buttons, relaxed fit, and minimal details that keep it feeling casual (like a buttonless collar and seamless front placket). It’s made in Canada from sustainably sourced 4.4 oz cotton (which is fully opaque) and available in sizes XXS – 3XL. So if you’ve been on the lookout for the perfect white oxford shirt this is my top recommendation for sure.

Read on for my notes on four elevated but easy-going outfit ideas that you can build with any button up in your closet!

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I’ve been wearing and washing my Tailor Shirt for many seasons now and it has become softer and comfier with time. It always comes up looking bright white and while I love how it looks air dried (shown above), a little steam ironing will restore its sleek, crisp texture.

This shirt fits true to size (I’m wearing a M and usually order a S or M in tops) and there are lots of model references and garment fit notes on the product page.

You can also read about all the notable details and elements that make this particular shirt a unique and truly timeless classic in my original post here.

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LOOK 1

For this look I styled the Tailor Shirt open over a fitted white long sleeve crewneck with a wide leg olive green trouser and minimal white sneakers. I added a warm sweater over the shoulders for a touch of cosiness and added a black cross body bag to keep the layers held in place. I love this one for a creative office, casual workplace, a day of meetings and errands or just as a fresh, layered look on a warm fall day.

THE TAILOR SHIRT (gifted in 2021) STYLEBEE10 for 10% Off | MICRO RIB PIMA COTTON LONG SLEEVE | PLAZA TROUSER (olive sold out, black linked) | LOW 1 WHITE SNEAKER (full review here) | ALPACA CREWNECK (warm Taupe) | ELOISE BAG (old, similar linked) | All accessories from my Minimal Jewelry Capsule.

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LOOK 2

The next way I styled the Tailor shirt is probably my favourite way to wear it, which is tails out over a pair of trousers, layered under a sweater vest. I love the androgynous, collegiate vibe this look gives and that it’s incredibly comfy while still looking put-together and intentional. With a vintage houndstooth coat, chunky boots and a brown tote bag, this one is perfect for any occasion on your fall calendar.

THE TAILOR SHIRT (gifted in 2021) STYLEBEE10 for 10% Off | BOILED WOOL JERSEY PLEATED LANTERN PANT (gifted by Eileen Fisher, I LOVE these pants) | CORTINA BOOT (more on my winter boots here) | SWEATER VEST (colour way old, linked to current option) | TOTE BAG (old, similar linked) | All accessories from my Minimal Jewelry Capsule.

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LOOK 3

Whenever I’m in doubt about what to wear, I know that a white button up and jeans will never steer me wrong. I wanted to test out The Tailor with my newest fit obsession, which is a high rise, super wide leg, full length jean, in a vintage wash. I kept the tuck pretty loose, rolled the sleeves and left the top few buttons undone for a very Jenna Lyons meets Katharine Hepburn moment. I love this base with a classic sneaker like my Chuck Taylor High Tops and a relaxed trench coat. Layered gold necklaces are the perfect touch for a bit of polish. This is definitely a look I’d wear while traveling or grabbing dinner with friends.

THE TAILOR SHIRT (gifted in 2021) STYLEBEE10 for 10% Off | CURVY SUPER WIDE LEG JEAN (varian wash sold out, similar here, true to size) | CHUCK TAYLOR 70’S HIGH TOP | SWEATER VEST (colour way old, linked to current option) | HEADBAND BAG LEE15 for 15% OFF | All accessories from my Minimal Jewelry Capsule.

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LOOK 4

For the last outfit in this styling session I wanted to try for something that could work in a more conventional professional setting. I decided to layer the Tailor shirt underneath a lightweight knit (cuffs folded out) paired with a black dress pant. I tucked the shirt into the pants entirely and then I only front tucked the knit so that it wouldn’t feel too bulky through the waist. A black belt helps to keep everything in order and black boots offer continuity through the lower half of the look. I added a statement coat and a chic suede bag to add extra sophistication and presence to the look.

THE TAILOR SHIRT (gifted in 2021) STYLEBEE10 for 10% Off | WAY-HIGH DRAPE PANT (true to size) | BLACK GLOVE BOOT (sold out, similar linked) | ALPACA CREWNECK (warm Taupe) | PRISMATIC BAG gifted | BUFFALO CHECK WOOL PEACOAT (sold out, similar linked) | All accessories from my Minimal Jewelry Capsule.

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WANT MORE STYLING IDEAS?

Be sure to explore this styling post where I share another four ways to style The Tailor Shirt for fall and this Pinterest board where I’ve been collecting ideas for Oxford Shirt Styling over the years.

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THANKS FOR TUNING IN!

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STYLEBEE10 for 10% Off

Valid on first orders of regular priced styles anytime. Code will automatically apply at checkout. Free returns and exchanges in Canada.