Let’s be real: getting dressed during that awkward winter-to-spring transition can sometimes be difficult (are you supposed to dress for warm or cool weather?!). Luckily, that’s where these loose, stretchy dresses come into play. We found figure-flattering picks that make it easy to look pulled together. Think soft fabrics, forgiving fits, and silhouettes that work now with a jacket and later without.
We rounded up 13 dresses worth obsessing over from Amazon, Nordstrom Rack, Anthropologie and Old Navy. Expect everything from lightweight sweater dresses to dressier maxis and minis. Most styles come in multiple colors and sizes, which makes it easy to find an option you’ll want to wear on repeat. Plus, they’re all under $75 (so you really can’t go wrong).
Loose, Stretchy Dresses for Winter-to-Spring
1. Our Favorite: Simple and comfy, this roundneck dress is our top pick for winter-to-spring weather. Pair it with a jean jacket and boots on chillier days or sans sweater with sneakers for warmer ones.
2. Runner-up: This polo mini dress is constructed from breathable cotton, and the stripes are perfectly on-trend. The loose fit skims over curves without clinging.
3. Casual-Chic: Available in 12 different colorways, this boatneck T-Shirt dress is a stunner for brunch or running errands. It’s lightweight, yet can easily be layered with a long-sleeve underneath.
4. Designer-Looking: Channel your inner ‘rich mom’ with this floral dress, which looks like it retails for hundreds (but is under $50). The floral pattern is dainty and looks stunning with a cardigan and ballet flats.
5. Everyday Essential: Easy, breezy and relaxed, this crewneck maxi dress from Old Navy is a no-brainer for transitional weather. The versatile, loose shape looks dynamite on all frames – and we’re obsessed with the side slit.
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6. Funky Front Zip: Whether you’re running errands or headed to your kid’s soccer game, this long-sleeve mini dress is the perfect choice. The top half looks like your fave sweatshirt, and the flowy bottom keeps the vibe polished.
7. Dressy Occasion: Keep it dressy with this budget-friendly twist-front midi dress. The jersey material is stretchy and figure-flattering. We’re absolutely swooning over the side clasp hardware.
8. Transitional Long Sleeve: Yes, a sweater dress is lightweight enough for winter-to-spring weather. The stretchy, breathable material keeps it from being stuffy, and the V-neck adds interest.
9. Dainty Darling: This maxi dress is flattering for any frame because of the loose, flowy fit. And yes, reviewers say it even has functional pockets.
10. High Low: The trapeze dress is making a comeback – especially when it has three-quarter sleeves, which are transitional-weather-friendly. Take yours from work to cocktail hour in a snap by adding a pair of heels and some hoops.
11. Lightweight Stunner: If you tend to get sweaty, this flowy racerback dress is quick-drying and features a flattering skirt that floats over any problem areas.
12. Easy-to-Wear: Short flutter sleeves and a shirred bodice make this maxi dress seem particularly ethereal. We’re envisioning this with a cropped, boxy jacket and a statement-making bag.
13. Preppy Dream: Layer this cheetah print sweatshirt dress underneath a wool vest for a prep-school vibe on colder days. For warmer temperatures, add sneakers and a waist-cinching belt.
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