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6 Easy Ways to Style a (Comfortable) Classic Button-Up

6 Easy Ways to Style a (Comfortable) Classic Button-Up

Work, Errands or Dinner Plans? The Comfy Button-Up does it all.


Here at Encircled, we believe in clothing that is versatile to keep you best dressed for any occasion. Plus, wearing your clothes as much as you can is our top sustainable style tip! 

Whether the occasion is work, a casual outing or a dressy evening, here are 6 classic button up shirt outfits, featuring our very own The Comfy Button-Up Shirt - A timeless, elevated design that's actually comfortable.


1. The Comfy Button-Up Shirt + The Dressy Sweatpant + Mules 

For this outfit, we put together The Comfy Button-Up Shirt with The Dressy Sweatpant to achieve the ultimate office friendly, yet comfy look. Shown in the colour Wheat, we tucked in the shirt just enough to gently change the shirt’s silhouette. (A quick styling tip: tucking in the very front of the hem will elongate the legs and make you look taller). With cuffed sleeves and a higher v-neckline, an extra touch of elegance is added to this work appropriate style. Easily paired with tapered dress pants or tailored black joggers, throw on your favourite mules and be ready to take on your day’s work feeling confident and comfortable. 


2. The Comfy Button-Up Shirt + Denim + Sneakers 

A button up shirt and jeans is the perfect outfit for a morning coffee run or trip to the grocery store. Made to be versatile, this classic button-up can be easily dressed down for the days you want to relax. Wear the shirt untucked to let the hem drape freely with your contours. The breathable and ultra soft fabric features 4-way stretch to move with you throughout the day. We styled this outfit with a pair of medium wash denim and depending on the length of the jeans, you can also try rolling up the leg cuffs for a suitable spring feel. Before you head out the door, put on your trusty white sneakers and throw your hair back with The Renew Scrunchie for the added benefit of functionality.


3. The Comfy Button-Up Shirt + The Comfy Wide Leg Pant + Heels

Here to dress up a timeless button-up is The Comfy Wide Leg Pant. Designed for both the office and evening outings, this transitional clothing piece pairs beautifully with a white or cream shirt. For this style, put on your favourite pair of black high heels and tuck in the shirt to enhance the shape of your waist. As the shirt and pant are both machine washable, wave farewell to your dry cleaning bill. Made from breathable micro modal fabric, the pant merges dressy with the comfort of wearing sweatpants. Plus, both The Wide Leg Pant and The Comfy Button-Up Shirt feature subtle pleats, making the outfit an absolute match.

4. The Comfy Button-Up Shirt + The Dressy Legging + Mules

As another ultra comfortable look, this work from home outfit will prepare you for any virtual meeting. Worn untucked, this versatile shirt was designed with a shirttail hem, meaning its length hits perfectly at the hips and is longer in the back. Ideal to wear with The Dressy Legging, the pairing beautifully complements the shirt’s flowing silhouette. Made from a blend of Rayon from Bamboo ,  the luxuriously soft leggings feature two side pockets and elongate the legs. For when the weather’s a little chilly, consider throwing on The Comfy Puff Sleeve Cardigan as a cozy solution. Lastly, finish this look with black mules or loafers and be ready to leave restrictive clothing as a thing of the past.


5. The Comfy Button-Up Shirt + Denim + Heels

Styled for a late patio dinner with friends, we paired The Comfy Button-Up Shirt with some dark washed skinny jeans. To look more sophisticated, black or grey denim is a simple transitional piece that can quickly dress up your outfit. For that elegant feel, the shirt is best worn untucked to let the fabric drape softy over the hips. With stretch fabric and OEKO-TEX® standard buttons, you can stay worry free as this button-up removes button gape out of the picture. No more discomfort or exposure concerns, slip on a pair of black heels and you’ll be ready to take on whatever the night offers. 


6. The Comfy Button-Up Shirt + The Dressy Sweatpant + Sandals 

As the weather gets warmer, keep it casual with this springtime outfit. With flowers and plants beginning to bloom, it's always refreshing to add some colour into your wardrobe. Styled with one of our favourites, The Dressy Sweatpant looks comfortable and fresh with a tucked in button-up. In the case you're looking to switch it up a little bit, you could even wear The Sleeveless Unbodysuit for an underlayer, and wear the button-up as a light cardigan. To complete this spring look, break out those sandals you’ve ignored for too long and be ready to go about your day looking classic and feeling comfortable. 


For more Encircled styling tips, check out these posts:


Which look will you try?

Comment your favourite outfits below. We would love to know what you think!



This helps me a lot, thank you.


Thanks for this, really a big help. Continue to share your unique ideas.


Adorable! All your clothes are great. Keep sharing!

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