Outfits to wear with Leggings, any day of the week

April 14, 2020 5 min read

dressy legging from encircled

Elle Magazine once said that sportswear, and leggings were on the way out. Well, they couldn’t have been more wrong.


The demand for leggings has skyrocketed over the past few years and with the normalization of working from home well... to say that we’ve been living and breathing leggings 7 days a week- no matter the event, is no understatement. We’re loving our leggings for the comfort they bring. Leggings are just so easy to style and too comfortable to take off. Pull on and go - as simple as that


Legging outfits can still pose some questions on style though. Is it worth dressing up leggings if you’re just working from home? Do business casual leggings exist? Does it even matter what you wear while staying in? Can leggings be worn as pants? Despite being the comfiest and easiest item to style, outfits with leggings can cause a stir amongst even the most fashionable. But, according to Reader’s Digest, how you dress can impact your mood - positively or negatively. So, for those of us loving legging outfits everyday day of the week, read on for some style inspiration and learn how your work from home uniform can be dressed up or down for times when you need to leave the house.


And for those of you who are still skeptical of their versatility and wondering how to dress up leggings - read on to meet your new favourite wardrobe staple.


Legging Outfit Ideas

We know life gets busy and things come up so we’ve split up our style guide into two legging outfit suggestions to cater to all sorts of events- how to dress up leggings for those days where business casual legging attire is needed and legging outfits to keep comfy, because some days lounging in your coziest clothes is just needed. 


Here are endless ways to style your leggings.


How to Dress up Leggings

Aside from their level of comfort, leggings are a great capsule wardrobe staple because they can be dressed up for so many different occasions. From working from home and having virtual meetings throughout the day to running errands or even going out to brunch or dinner with friends, dressy leggings outfits are easy to style for all seasons.


Boardroom Boss: Leggings with blazers


how to style leggings with a blazer

From business professional to business casual leggings, pair your favourite pair of dark coloured leggings with a blazer and top for a polished look. The blazer will add length to your outfit and balance the look while the dark coloured leggings will maintain a level of professionalism. Mix up your dark tones and wear dark navy blue leggings with a black blazer for a fun take on a sharp outfit. Our Dressy Leggings are perfect for this - comfy and casual underneath but business appropriate to the eye.


Business Casual Cardi: Leggings with cardigans


how to style leggings with a cardigan

Opt for a more casual leggings outfit by pairing leggings with a cardigan. Adding a layer of dimension, this business casual leggings outfit is perfect for running errands or a more relaxed office environment. Finish off the look with a statement necklace or shoe such as dressy booties or knee length shoes.


The Dress(y) Leggings: Leggings with dresses


how to style leggings with a dress
Photo credit: @acjarrett

Dress up your look - literally, my pairing legging under a dress for the colder months. Swapping thin tights for cozy leggings provide more coverage and warmth, and maintain the level of professionalism within your outfit (no one will ever know you’re wearing your fav. loungewear under there). This tip is perfect for those looking for leggings outfits for work.


Long Lines: Leggings with long blouses


Photo credit: @sarebellamy

Long shirts to wear with leggings are the perfect option for those looking for more coverage as they head to the office or make their way through town running errands. For a more polished look, belt your long top at the waist, adding a layer of dimension to your legging outfit for work. A sleek black leather belt is classic, or opt for a bright red belt if paired with dark navy leggings and a white shirt for a pop of colour. No belt? No problem, tuck your shirt in for a classic french tuck.


Casual Legging Outfit Ideas

So, you’ve dressed up your leggings for work but are now looking for outfits with leggings that will satisfy your more casual weekend activities without looking sloppy or tired? We’ve got you covered.


Workout Wear: Leggings with hoodies/sweaters


how to style leggings with a hoodie

What’s more casual than leggings with a classic hooded sweatshirt? Wear your comfiest pair of leggings with an oversized sweatshirt like The Fair Cloud Terry Hoodie for the ultimate weekend outfit. Great for rainy days at the cottage, binge watching tv or even heading out to grab a few last minute snacks. Style this look with a classic ball cap or retro fanny pack to finish off the outfit.


Jean Jacket Joy: Leggings with jean jackets


dressy legging outfits

Pair black leggings with a jean jacket, white t-shirt and casual sneakers for the ultimate weekend outfit. Polished with the matching white t-shirt and sneakers, this look is dressed down by the jacket but remains stylish for brunch, a walk through the park or even a quick trip to the grocery store.


Lounging in Leggings: Leggings with long shirts


how to style leggings with a long shirt

Dress down your long shirts to wear with leggings by adding cozy socks during the cooler months or simply pair your leggings with your comfiest long sleeve for an effortlessly cool look. If you’re headed out of the house and are looking to polish off your style, pair your look with an oversized scarf for a balanced yet cozy look.


Whether you’re looking for leggings outfits for work that need to be dressed up or opting for a more casual look, it’s all about the accessories! Statement shoes like black leather boots or heels dress up an outfit while sneakers and sandals give off a more casual vibe. Pairing your outfit with a belt can make all the difference to polish off an oversized blouse and adding jewelry like necklaces and rings really display the extra bit of effort made to complete a dressier legging outfit.


Lacking a go-to legging? We've got you covered!

For an elevated legging that can go from work to weekend with ease, try out our Dressy Legging. Featuring edgy style lines, luxurious bamboo legging fabric, and pockets, these leggings do it all.


For the perfect everyday legging, try our Fair Legging. A classic high-rise legging, butbetter made better. They’re crafted with our luxuriously soft, eco-friendly 4-way stretch fabric that’s dyed and milled locally. The Fair Legging features a wide comfortable waistband for a seamless silhouette and a minimalist design.


For the warmer months or more active events try our Fair Crop Legging. Made from an ultra-soft, stretchy Bamboo blend fabric, this flattering cropped number has a fitted silhouette and high waisted band, sitting at the natural waist for a comfortable go-to wardrobe staple. 


Which outfit is your favourite? Comment below, we’d love to hear how you style legging outfits!


All photos are copyright Encircled. Contact us for permissions/rights to re-use or repost images.

Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is Made in Canada, out of sustainable, and eco friendly materials.

Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is ethically made, out of sustainable and eco friendly materials.Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is ethically made, out of sustainable and eco friendly materials.Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is ethically made, out of sustainable and eco friendly materials.Travel Essentials. Encircled creates versatile minimalist clothes with the everyday traveler in mind. Each piece is ethically made, out of sustainable and eco friendly materials.

Leave a comment

Also in The Journal

8 Actions You Can Take to be a Part of The Fashion Revolution Week!

April 20, 2022 4 min read

Are you Familiar with Fashion Revolution Week? 

It’s the week that brings together the world’s largest fashion activism movement for seven days of action surrounding the anniversary of the Rana Plaza factory collapse. In this post we'll give you 8 Tips on how to be a part of The Fashion Revolution.

Read More
Sustainable Spring Capsule Wardrobe

April 05, 2022 3 min read


Spring has officially sprung, and that means it’s time to pack up the puffer jackets and switch over to a spring capsule wardrobe. So, if you’re in the process of planning your spring wardrobe, you’ve come to the right place!

Read More
7 Women-Founded Brands You Should Know

March 08, 2022 4 min read

To celebrate International Women's Day, we highlighted some of our favourite women-founded brands doing amazing things!

Read More