Since I first discovered Gap Factory, it has been a welcome resource for finding comfy, cute and affordable (with an emphasis on affordable because I’m a girl on a budget at the moment) items. Gap Factory has become my go-to for easy, everyday style and budget-friendly styles. Every time I shop at Gap Factory, I’m always pleasantly surprised by how good their stuff really is. In fact, some of my most-worn pants have come from there. When you want to make dressing super easy and comfortable, Gap Factory has tons of great options.
And just in case you doubt my sincere love for Gap Factory, here is how I rolled up to my local store for my try-on: decked out head-to-toe in all Gap Factory pieces I already owned.
Gap Factory Winter Outfits: Cute, Comfy & Budget-Friendly Finds
Coat (S) | Sweater (S) | Cords (4) | Boots (8)
Cold-weather dressing should feel cozy and uncomplicated, and that’s exactly where Gap Factory shines. It’s one of my favorite places to find winter staples (for example, this Puffer is SO good) that don’t feel stiff or overpriced, which is a win across the board. I love that their pieces (like these pull-on pants and these dark green floral jeans) are easy to wear, and designed for everyday life.
If you like comfy/cute pants, then this post is for you!
Outfit 01 | But First, These Dark Floral Barrel-Leg Jeans
I finally got a chance to try on these dark floral barrel-leg jeans I’ve been eyeing for months and they were even better in person.
Sweater (S) | Jeans (4) | Boots (8)
These jeans are such a fun and affordable way to shake up your denim rotation. This print is rich and romantic and I love that it can work in both winter and spring. It feels fresh and unexpected, but still totally wearable with a simple tee or oversized sweater like this ForeverCozy Oversized Sweater that is top rated. The sweater is on major sale (33% off, plus an extra 60% off at checkout) and comes in 7 other colors including a lovely deep green.
Sweater (S) | Jeans (4) | Boots (8)
Fit Notes: These jeans fit true to size, if just a little large. They are the same style and fit as my eggplant corduroys. They are made from 98% cotton and 2% elastane and are machine washable. The sweater runs large and features an oversized silhouette and that hits below the hips. It is made from 75% acrylic, 22% recycled polyester and 3% spandex and is also machine washable.
Outfit 02 | Fair-Isle and Super Soft Pull-on Denim Joggers
You know I can’t resist a fair-isle sweater but the true winner of this outfit are these Super Soft Pull-on Denim Joggers that I was not expecting to love so much.
Sweater (S) | Joggers (S) | Boots (8)
I didn’t think I was much of a denim joggers gal until I gave these a try. I think why I love them is the barrel-leg fit and they are like, super-duper comfy, thanks to the soft denim, relaxed silhouette and the cinched waistband. But the tailoring and seam work keep them from feeling sloppy. They are the kind of pants you will reach for when you want comfort but not leggings. And the fair-isle sweater also comes in a grey and light blue option as well as a few non fair-isle prints. It’s super soft and lightweight.
Sweater (S) | Joggers (S) | Boots (8)
Fit Notes: These pull-on denim joggers run a little large but I would still order your usual size, the baggy look is really in right now. They are made from 55% cotton, 40% tencel and 5% recycled cotton and come in a slew of wash options including animal print. The fair-isle sweater features a wide, ribbed turtleneck and flared cuffs. It’s soft and lightweight and runs slightly large. It’s made from 75% acrylic, 22% recycled polyester and 3% spandex. Machine washable, lay flat to dry.
03 | A Pretty Print Midi Skirt for Winter? Yes, Please!
Okay, this pretty floral midi skirt may not be exactly Michigan winter-proof but it was so pretty and so up my alley, style-wise that I had to get it (and it was almost 60 degrees here just the other day). Also, it’s on bonkers sale at 58% off plus an extra 60% off at checkout which makes it literally 10 dollars!
Sweater (M) | Skirt (S) | Samba Janes (7.5)
This floral skirt adds instant depth to your outfit with it’s rich colors and easy, flowy shape, making them a great alternative to jeans when you want something a little more elevated. It looks cute styled with this oversized sweater, or a soft cashmere sweater, knitted tights, tall boots and a structured coat for contrast. It’s an effortless way to mix pattern and polish this winter.
Sweater (M) | Skirt (S) | Samba Janes (7.5)
Fit Notes: This skirt runs true to size and also comes in a navy polka-dot option. It features an elastic waist, seam detailing and and slit at the front. It’s mid rise and features a slightly asymmetrical fit that hits below the knee. It’s 100% rayon and machine washable.
04 | A Moment for this Pretty Quilted Puffer
I didn’t go into Gap Factory with the goal of trying-on outerwear, although, they have some really great outerwear, like this relaxed puffer, but I couldn’t resist picking up this ‘sunny grey’ relaxed quilted nylon puffer jacket, which reads more as a lovely ‘light-blue’ than ‘grey’, IRL.
This quilted puffer jacket features a lightweight yet insulating fill and a slightly structured silhouette that keeps you warm without the bulk, making it a practical cold-weather staple. The all over quilted wave pattern adds some dimension and maintains a minimalist vibe. It also comes in olive, navy, ‘birch’ white and a lightish brown option and is currently 60% off.
Puffer (S) | Pants (M) | Boots (8)
Fit Notes: This jacket runs true to size is made from 100% recycled wellon fill and has a quilted outer. It has dropped sleeves, patch pockets and elastic cuffs. It is made from 100% nylon.
05 | The Striped Pants that Surprised Me the Most
Well, I was not expecting to love this striped high rise easy wide-leg khakis as much as I did. Maybe it’s because I sized up for a more slouchy fit but they have such a cool, oversized fit.
Hoodie (M) | Pants (M) | Boots (8)
These striped pants combine classic tailoring with a modern twist the slightly relaxed fit keeps the silhouette effortless and wearable and vertical stripes help elongate your frame. Crafted from a soft, mid-weight fabric with just enough structure to hold it’s shape, they are comfortable enough to wear all day long yet polished enough for outings. These pants are just cool without trying to hard.
Hoodie (M) | Pants (M) | Boots (8)
Fit Notes: These pants fit true to size (although I sized up for a more slouchy fit) and come in regular, petite and tall sizing as well as 6 different color/print options. They feature a stretch, twill weave, an elastic waist, a zip fly, with front utility pockets and back patch pockets. They are high waist with a 27″ inseam and are made from 97% cotton and 3% spandex.
06 | Baby Blue Stripes + Front Yoke Barrel-Leg Jeans
You might be noticing a pattern: I love blue, especially light blue, so this CashSoft Relaxed Sweater Polo Shirt stopped me in my tracks immediately. I love the pop of red stripes too. Also, I love jeans with unique details and these front-yoke barrel leg jeans add just the right amount of interest.
Sweater (S) | Jeans (6) | Samba Janes (7.5)
This super soft striped blue polo sweater offers a fresh take on a classic knit, with crisp stripes and a relaxed silhouette that feels both polished and easy going. It’s lightweight and it’s soft, cozy fabric makes it perfect for layering over shirts or under jackets. And these front yoke barrel leg jeans bring a modern, flattering spin to denim and are easy to wear with their soft, yet slightly structured fabric.
Top (S) | Jeans (6) | Samba Janes (7.5)
Fit Notes: This soft, lightweight cotton blend sweater is made from 53% cotton and 47% nylon and runs true to size. It features henley button-front and a spread collar as well as ribbed cuffs. The jeans run true to size and are made of 94% cotton, 5% recycled cotton and 1% elastane. They are a medium weight and feature a yoke front seam. They come in short, regular and long lengths and the regular size has an inseam of 26″.
07 | A Cute Ruffle Denim Blouse + Pull-on Khakis
Back in the day, I graduated with a Masters in Elementary Education and taught in the Chicago suburbs and I feel like this ruffled blouse and pull-on khakis would be a perfect everyday fit for the classroom. It’s comfortable and classy and easy to move in.
Blouse (S) | Pants (S) | Boots (8)
This ruffled shirt paired with pull-on khakis is the definition of easy, everyday polish. The soft denim top adds subtle texture and interest with it’s ruffled neckline and relaxed fit, while still feeling casual enough for everyday wear. Together it’s an effortless outfit that feels pulled together without trying too hard, perfect for busy days when comfort and style need to coexist.
Fit Notes: This ruffled button-up top also comes in four different plaid print colored options and fits true to size. This denim option is made from 100% cotton and features long puff sleeves with button cuffs, dropped shoulders, half button front and ruffle trim around the neckline.
Blouse (S) | Pants (S) | Boots (8)
Fit Notes: These are same pants as the striped pull-on pair I am wearing in outfit four and outfit five but in a small instead of a medium so you can see that they are slightly more fitted and not quite so oversized (I usually wear a size 27/28 in jeans and I am 5ft7in).
08 | Houndstooth Wide-Leg Pants + An Oversized Denim Shirt
Together this cropped, oversized denim shirt and houndstooth wide-leg pants nails that effortlessly cool, relaxed and oversized vibe that still feels intentional.
Shirt (S) | Pants (S) | Samba Janes (7.5)
The washed-black button-down has a soft, broken in feel that keeps it casual, while the trousers are slightly more structured and add balance and a more polished edge. I love how the darker tones work together to create an easy, wearable look that doesn’t rely on trends but still feels modern. This look works in the office as much as it does running errands.
Pants (S) | Samba Janes (7.5)
Fit Notes: This cropped denim shirt is 100% non-stretch cotton and features a straight, cropped fit that hits above the hip. These pants run large and are made from 64% recycled polyester, 34% rayon and 2% spandex. They feature an elastic waist with front slant pockets in the front and back welt pockets.
As always, thank you so much for reading this post! If you have any questions or anything you’d like to see covered, just leave a comment and I will do my best to make it happen! Until next time,
xo, Jess ( My Instagram | More of My Posts )
