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5 Types of Shoes to Wear with your Dressy Sweatpants this Season

5 Types of Shoes to Wear with your Dressy Sweatpants this Season

This week, we answered a customer question about what shoes go best with a pair of our Dressy Sweatpants.

Q: What shoes do I wear with my sweatpants? I love my Dressy Sweatpants but always feel like I wear the same two pairs of shoes with them … I’ve seen sweatpants styled so many ways but never know where to start or how to create outfits with sweatpants.

Finding the perfect pair of shoes to match your outfit is something that has perplexed women for centuries. The average person experiences “wardrobe panic” at least 36 times a year, and with so many shoe options to pick from, selecting which clothes to wear from your wardrobe let alone which pair of shoes to go along can eat up a lot of your morning routine. 


As the saying goes, shoes can make or break an outfit. From the colour, style, height and material, shoes can blend into an outfit for a minimalist approach or can become your ensemble's focal point for a show stopping look. With sweatpants being the ultimate pant (a bold but true statement) their level of comfort and versatility must be appreciated. 


In order to make wearing sweatpants outside the house effortless and enjoyable, we’ve compiled a list of our favourite shoes to style with sweatpants. From sweatpants and heels to shoes with joggers, it’s all about playing with proportions and colour to either dress up your look or keep it comfy and casual so you’ll never have to wonder what shoes to wear with sweatpants.


Here are 5 options for different occasions and seasons that will mix and match with your sweatpants and ideally other outfits in your wardrobe.

How To Dress It Up

Dress up sweatpants? Yes it’s not only possible but encouraged. From cozy sweatsuit sets to joyful joggers, sweatpant outfits can be dressed up for most occasions. With the right pair of sweatpants, you can head to work, catch up with friends over brunch or run your weekend errands. To elevate this basic the key is to play with colour and material. 


Read on to find how you can seamlessly transition your everyday loungewear to cool and convertible sweatpant outfits.


 1. Ballet Flats

 A classic ballet flat pairs beautifully with a pair of sweatpants.


There are a myriad of dressy ballet flats in the market from dressy to casual, and selecting the right one to pair with your sweatpant outfit depends on the colour and material of the shoe. Neutral colours provide a touch of sophistication to your look so opting for colours like black, white, brown and navy blue allow for versatility across all of your wardrobe’s outfits. Including neutral coloured shoes in your closet also allows for increased styling options for your capsule wardrobe and ensures you can get the most out of your closet.


Selecting high quality materials as well will dress up your sweatpants outfit. We suggest opting for a pair of timeless soft or vegan leather shoes which will last for years to come and  have easy to follow care instructions. If you’re looking to mix up the ballet flats, try swapping in a pair of leather loafers with a wider leg sweatpant to give your outfit an effortlessly posh look. Loafers with a gold or silver buckle will also increase the level of sophistication to your outfit.


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.

We recommend sticking with a basic ballet flat or a cut-out (D'Orsay style) flat versus doing a strapped ballet flat which will not work as well with a pair of longer sweatpants as they will cover the extra detail. While minimalist shoes work well with longer, looser fitting leggings, we recommend wearing elasticated ankles with a bolder shoe such as a patterned loafer in order to properly showcase the shoe.


2. Booties

We love a good pair of shoe-ties (short + booties). We used to fear this shoe as our bottom half is curvier than our top, however, we've found that a good bootie can add interest to any outfit and help even out proportions. The extra height elongates the leg like a heel and a short bootie works well with a pant like the where you don't want to cover up the ankle details. Similar to ballet flats and loafers, neutral coloured booties work well with any outfit combination, add a classic staple to your capsule wardrobe and work well across seasons. The slight heel on the booties also adds an extra dose of dressy style to your sweatpants.


If you’re looking for more of an edgier style, we recommend tucking in a tighter fitting pair of sweatpants or ones with a tight ankle like a jogger into a chunky pair of boots. The tighter fitting leggings with the chunkier boot will ensure your sweatpant outfit doesn't look too bottom heavy and can easily be paired with a jacket like The Unmoto Jacket for a sleek look. Not sure which chunky boots work well with sweatpants? Try a pair of jet black combat boots or for a cool street style, opt for contrasting white combat boots which pair nicely with black, navy blue or grey sweatpants.


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.


3. Pumps

A heel is a work outfit essential. 

For work, choose a neutral shoe like black, white, navy or beige, or spice it up with a pattern. Easy patterns to pair will all wardrobe essentials include a black and white plaid, navy blue/white polka dot or an abstract pattern where the primary colour is a neutral tone. These versatile shoes will not only dress up a slim fitting pair of sweatpants for weekend brunch, but will allow you to dress them up with dress pants or keep it business casual with denim jeans.


When it comes to pairing sweatpants with heels, we recommend a more minimalist shoe for looser fitting pants while opting for strappier heels when it comes to slim fitting tailoring.


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.

A heel will really take your sweatpants to the next level. No one will know they are sweatpants (just you).


How To Dress It Down

Looking to keep your sweatpants outfit casual yet cool as you head out of the house? Pair your favourite pair of sweatpants with more casual shoes and materials for a look that remains stylish without looking sloppy.


4. Sandals 

For a warmer spring, and hot summer days, a flat sandal works well with sweatpants.

We love wearing our flip flops with sweatpants on a weekend when lounging about or heading to and from yoga. Spend the summer in sweats with our Fair Cloud Terry Jogger which goes nicely with any casual pair of sandals. From strappy, to heavy duty and everything in between, when going for a more casual look, all types of sweatpants - ranging from joggers to dressy sweats, pair nicely with sandals. To keep your look casual yet fashionable, wear your sweatpants and sandals outfit with a classic white tee, over the shoulder purse and your favourite pair of sunnies.


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.


Alternatively, you could add a dressier mule, or a more substantial sandal like a Birkenstock depending on your daily outings. The possibilities are endless!

5. Casual Runners

It seems almost too obvious to pair casual runners with sweatpants, right? Well, it works!

While more casual of a shoe, the style, colour and material of runners can all be experimented with to create a sweatpant outfits that match your personality. You’ll never have to wonder what shoes to wear with joggers or sweatpants again as anything from ordinary sneakers to brightly coloured high tops can be worn.


No matter your preferred colour and tailoring of sweatpants, we recommend investing in a pair of comfortable white sneakers which can be mixed and matched with all sweatpant outfits, dresses, summer shorts, jeans and outfits with leggings worn as pants. White sneakers will provide a casual yet timeless look to your outfit and will contribute to your capsule wardrobe basics. 


If you’re feeling as though white is too muted of a casual shoe, we recommend opting for a brightly coloured sneaker like bright red or blue which will draw the eye towards the floor, giving the appearance of elongating your legs. A great selection of brightly coloured sneakers can also be found amongst high top shoes like Converse, which pair well with any type of sweatpant. Or, for those looking to stay casual but require the extra height that pumps or booties provide, try platform sneakers.


There are now so many shades of 'casual runners' that can truly change your look (while not sacrificing comfort!)


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.


Sometimes the best look is to go with the flow of the spirit of the pants which are what the industry is calling 'athleisure'. 

A casual runner is also a good airport shoe and allows you to be ready for a workout anytime, anywhere.



Tips for Packing Shoes

  • As a general rule when packing for a trip that is less than 10 days, we try to limit ourselves to 3 pairs of shoes. This includes the pair of shoes we wear on the plane. 
  • Neutral shoes are always a good option because they go with many different outfits. A nude heel is our BFF.
  • Shoes are super heavy / bulky, so they can easily eat up loads of space in your carry-on. Wear your heaviest pair on the plane and to save space try packing socks or smaller clothing items in shoes like sneakers to maximize space. Need more advice on how to pack efficiently for your next trip? Read this article to start packing like a pro. 

Which shoe + sweatpant outfit is your favourite? Leave it in the comments below! 

If you have a question for us on how to style or wear your sustainable clothing designs, or general travel questions and tips, please contact us.


All outfit photos are copyright Encircled. You may use these with permissions but may not alter the photos. Please link back to our websites.


Pattie H

I wear all my Encircled leggings, be it the dressy sweatpants/fair leggings/dressy leggings/fair joggers, with Poppy Barleys. My go-tos are the At Leisure Slip On, the Two Point Five boots and any of my Birkenstocks. I leave flip flops for the beach and runners for running/sports. 😉

Patricia Russell

Love the look with the sandals and the pumps because I’m always looking for ways to look dressy with comfort. I am ALWAYS happy in Encircled clothing and you can dress them up. Thanks for sharing.

Bulet Kumar

Such a nice blog !!! Thank you so much for sharing for us. If you want to know more about best wear in summer, you can visit this site

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