The Dressy Sweatpant

Size Chart
Dark Grey
Dark Olive

Your new fav pant. The Dressy Sweatpant is easy to dress up or down because of the modern design and luxurious fabric that’s comfortable, breathable and sustainable. This fancy sweatpant features a tapered leg with ruching at the ankle.


Chic enough for the office and casual enough for weekends. The must-have pant for all seasons. Pair with the Dressy Sweatshirt and make a Dressy Sweatsuit.

          • A modern pant with flattering wide pleats and ruching at the ankle. Inseam 30”.

            Two side-slit pockets and a third back hidden zippered pocket. Sits comfortably at your natural waist.

            Comfortable and machine-washable 4-way stretch fabric that won’t bag out.

            Redesigned in 2019 based on customer feedback.

            Knit, dyed and sewn in Toronto.
          • Made from a blend of MicroModal® | Lycra

            Our MicroModal is knit and dyed in Toronto. MicroModal
            is a naturally derived, plant-based fabric cultivated from beech-tree pulp which is sustainably sourced in Austria, and neighbouring countries. Modal is made through an environmentally-conscious process where 95% of water and materials used to make the fabric are recycled. The fabric is also OEKO-TEX® Standard 100 certified which means it is free of harmful chemicals.

            Learn about our fabrics


          • Fit Advice:  We recommend staying with your typical size in pants. The cut on the Dressy Sweatpants is slightly looser in the leg, with a fitted waistband that sits at your natural waist.View the size chart

            Model's Measurements: Ashley
            shown in product photos wearing Black, Olive, Dark Grey is 5’7"/ size 4-6 and wearing an M. Kenna shown in product photos wearing Black is 5'7" / size 18-20 and wearing a L
          • Machine wash on the gentle cycle, preferably inside out in cold water. For best care, hand wash and hang to dry. Do not dry clean, and do not put in the dryer. A light iron can be used if needed, but please use a towel in between the iron and garment.




    0 - 2 (XS)
    4 - 6 (S)
    8 -10 (M)
    12 - 14 (L)
    16 - 18 (XL)
    20 (XXL)


    Customer Reviews

    Based on 195 reviews
    Love them!

    I have been an encircled fan for a few years but had yet to purchase their most famous piece. Finally decided to take the plunge. I am either a 10 or 12 in "regular" pants so decided to size down to the Medium and they fit perfect! I can see these being a staple in my wardrobe! Thank you, as always, for amazing clothes!!

    Hi Karen! Thanks for your review, we're so happy to hear that you're enjoying them!
    Love the new fit

    This is my third--and favorite--pair. I like the revised fit a lot (without the drop crotch)--I'm glad I didn't order the black until this time (first 2 were gray and olive). I didn't need the extra length, but it fits just fine. All are super comfortable and I love wearing them!

    Hi Irene, thank you for your review! We're so happy your enjoying the redesigned Dressy Sweatpant!

    I've had these pants for over 4 years and love them. Perfect for travel or a night out. I don't wear them casually because I don't want them to wear out. Sadly the new version will be way too long; I'm 5'2". I've never needed the back zippered pocket -- too small & awkward.

    So comfy

    I call these dressy pajama pants. Not because they look like pajamas but I feel like I’m wearing pajamas. I wore them with heels to church, flip flops around the house and cute sandals to work they are very versatile depending on the shoes and type of shirt you pair them with. I cannot wear them on my waist however it just is very uncomfortable for me to wear clothes that high but it works to wear them lower- it does give a very slight harem look but I like the slight baggier style. If you want them tighter you have to pull them up pretty high if you’re short. My one complaint is what other people have mentioned about the elastic for the waistband. Why such a small elastic band?? Even though they are comfortable I have to either fold the thin elastic band over or under and regardless of either way I fold it it does leave a imprinted mark on my skin. It definitely needs a wider elastic band or just make that whole waist panel a very lightweight loose elastic. If I were the Encircled designers I definitely would be looking to redesign that aspect. I will definitely be keeping these but if I’m forking out $150 for a pair of pants I feel like they shouldn’t leave marks on me. I’m 5’2.5” about 125 lbs and got the small. Mediums would be way too big. Other than the thin elastic waistband I love these pants and will probably order another pair.

    Hi Maggy, thank you for you review! We truly appreciate honest customer feedback and your comments will be shared with the production and design team!
    Almost perfect pants

    I have had these pants for a few months now and they are comfortable and I do love them, but.... I only wear them at around the house, they could be dressy enough to wear out but the length ruins it for me. The fabric is great, but the length is far too long.... I'm 5 foot 3 and the ruching at the bottom bunched up so the pants looked baggier than they are (more like harem pants). I considered getting the ends taken up and cutting off all the ruching... making the pants looking less tailored. But in the end, I did get the pants taken up at the bottom hem and it looks even more baggy. The rest of the pant is awesome.... please Encircled, make these pants in a petite version! I would buy them in ever colour if they made the same pants for us shorties! For those of you who are short like, beware, you will probably have to take up the hems, and the ruching detail will be destroyed!