5 Different Ways I Style Sweatpants
I know, I know—styling sweatpants isn’t exactly rocket science. But I’ve always found it a little tricky when it comes to pairing them with a bag or purse. Obviously, sweatpants naturally give off a chill, effortless vibe, so not every handbag fits the look. A structured tote can feel too formal, so I try to style them with a slouchy or crossbody bag. These are my go-to looks for running errands, grocery store trips (yes, I freeze in A/C), or when I’m on Aunt duty. Sweatpants are basically my summer staple because I’m that person who’s cold inside but still wants to be comfy and cute. Some of these outfits even work for those spontaneous “let’s grab dinner” texts from the girls. I keep layers in the mix so I won’t overheat if I end up outside in the sun for a bit.
Look 1: Lime Tee + Sweatpants
This outfit is perfect for days when you know you’ll be outside a bit—maybe on your way to the mall, or just looking to elevate a casual day. The lime tee makes the whole look pop. It’s bold, bright, and definitely the star of the show.
I love pairing this with a clutch purse to make things feel a little more chic. My go-to is one with a beachy vibe: light beige and cream with a woven texture. It adds just the right amount of subtle detail without overpowering the look. Honestly, this outfit even works for a cute, casual date night with the boyfriend—cozy, real, but still put together.
For days when I’m on Aunt duty, I switch out the clutch for a fun oversized beach bag with blue and green stripes. The green ties in perfectly with the tee, and the stripes give the outfit a playful, put-together feel. Plus, I need the space! It fits my nephew’s things and mine. I would even wear this outfit after a long day of swimming at the water park. It keeps me cozy.
Shoe-wise, this outfit plays nice with almost any Adidas style—lime, green, black stripes, take your pick. It’s chill, functional, and still eye-catching.
Shop the look:
Lime Tee by American Eagle (similar here)
Sweatpants by Aerie (similar here)
Clutch Bag by Caroline Hill (similar here)
Beach Bag (similar here)
Look 2: Graphic Tee + Sweatpants
This look is all about cozy-meets-cute vibes—and I’m here for it. The graphic tee I’m wearing has a soft butterfly print from Aerie, and I love the dreamy blue and purple hues. It’s an outfit that practically begs for a night in: pick your favorite rom-com (or action movie), grab a bowl of popcorn, and snuggle up on the couch for a laid-back date night with your beau.
But it’s not just for lounging. This outfit works perfectly when I’m on Aunt duty, too. It’s comfy enough to keep up with a little one running around the house, and still cute enough that I feel like myself.
When I need to step out for a quick errand run, I’ll throw on a crescent bag—mine’s a super soft sherpa material, which just adds to that cozy vibe. On busier days, I’ll reach for a sporty crossbody bag instead. It's lightweight, hands-free, and ideal for school pick-ups, soccer practice drop-offs, or even a park birthday party. No fuss, just function—with a little flair.
Shop the Look:
Graphic Tee by Aerie (similar here and here)
Sweatpants by Aerie (similar here)
Crescent Bag by American Eagle (similar here)
Crossbody Bag by Offline by Aerie
Look 3: The “Chessy” Vibes – Jean Button Up + Sweatpants
This look gives total Parent Trap energy—specifically Chessy from the Lindsay Lohan version. You know, the jean shacket-wearing, warm-hearted aunt figure who made grilled cheese feel like an act of love? I’ve always adored her character, and this outfit feels like my own little nod to that era.
I throw on a jean button up over my sweatpants and immediately feel like I’ve stepped into my “cool aunt” era. It’s giving comfort, support, and a little 90s nostalgia in the best way. To modernize the look just a bit, I paired it with a cream leather bag. It’s slightly structured but still has that casual, slouchy feel that makes it easy to wear. The clean, updated shape balances out the retro vibe of the outfit perfectly.
Whether I’m dropping by for a family visit or just channeling my inner Chessy, this look is a quiet favorite. It feels like a hug—with style.
I also pair this look with an oversized beach bag—mine has a fun jungle theme that adds a pop of personality. It gives off easy summer vibes but also happens to be super practical, especially when I’m hanging out with the family. Whether it’s snacks, sunscreen, or random toys, this bag holds it all.
Shop the Look:
Jean Button Up by Dear John (similar here)
Gray Tee by American Eagle (similar here)
Sweatpants by Aerie (similar here)
Cream Bag by Anthropologie (similar here)
Tropical Beach Bag (similar here)
Look 4: Oversized + Sweatpants
This fourth look is one of my absolute favorites because it’s perfect for travel. Whether I’m headed on a long car ride for a weekend getaway or racing through the airport to catch a flight, this outfit has me covered—literally and comfortably.
The base is simple: classic sweatpants paired with an easy, oversized sweatshirt for when the A/C hits way too hard. But what really elevates the look is the bag. I pair it with a structured emerald purse that adds just the right amount of color and polish. The rich green feels fresh and fun, and it gives the whole outfit a little extra personality—like, “Yes, I’m comfortable, but I’ve still got it together.”
The best part? The bag isn’t just cute. It’s enough for all my essentials—lip plumper, body mist, and face sunscreen. This look is proof you don’t have to sacrifice style for comfort when you’re on the move.
Shop the Look:
Oversized Sweatshirt by American Eagle (similar here)
Sweatpants by Aerie (similar here)
Emerald Crossbody Bag by Hobo (similar here)
Look 5: Tank Top + Sweatpants
This last look is all about having fun with cozy pieces in unexpected ways. It’s perfect for a laid-back date night with your boyfriend or a sunny trip to the farmer’s market when the heat is real. I paired it with a crescent bag to give it a slightly more festival-ready vibe—effortless but intentional.
Another way I would wear this look is when I’m heading to or from yoga. I’ll swap in a white sports bra and bike shorts underneath the sweatpants, just in case I want to shed layers. On those days, I pair it with a black shimmer crochet bag. It adds a touch of texture and sparkle while keeping things sporty and functional. The overall vibe is beachy-meets-athleisure, which honestly might be my favorite combo.
Whether you're keeping it chill with your person or just trying to stay cute on the go, this look proves that sweatpants can really go wherever you do.
Shop the Look:
Tank Top by American Eagle (similar here)
Sweatpants by Aerie (similar here)
Crescent Bag by American Eagle (similar here)
Beach Bag by Aerie (similar here)
