I know it truly feels like summer in other areas of the country but here it’s been chilly, rainy and downright dreary on and off for the last couple of weeks. Dressing for this type of weather can become monotonous– button-down, jeans, flats, and don’t forget the umbrella. But I’ve been daydreaming about the sweater/dress combination (or any sweater/tea-length skirt combo for that matter for a while now). For starters, these outfits are incredibly easy to throw on and go. You can be comfortable all day and into the evening. The combination is also great weekend wear. Have a boat day or picnic coming up? A light sweater paired with a dress is the perfect outfit for activities. Sweaters with dresses are also a great way to embrace the warm weather in the daytime and protect yourself from the chill at night. This outfit can be worn in Minnesota for the next 4-8 weeks and I’ll definitely wear this combo as often as I can.

I love the idea of a pair of slip-on sneakers with a bright sweater and skirt. Great for when the weather is unpredictable but you still want to feel fun. Don’t forget the shades!

FRAME – Cutout Ribbed Merino Wool-blend Sweater – Tomato red • Frame • Sold Out
Women’s Chelsea28 Ruffle Midi Skirt • Chelsea28 • Sold Out
Comme des Garçons – Leather Pouch – Black • Comme des Garcons • $135
Vans White OG Classic Slip-On Sneakers • Vans • Sold Out
Le Specs Neo Noir Sunglasses • Le Specs • $59

Monochrome never goes out of style. The sweater/skirt combo gets a workwear update with a button down underneath. Add some classic white sneakers and you’re good to go.

The Elder Statesman – Intarsia Cashmere Sweater – Black • The Elder Statesman • $1,715
Frame Denim button down shirt • Frame • Sold Out
DKNY – Ribbed Stretch-knit Midi Skirt – Black • DKNY • $220
Cynthia Rowley Felix Fringe Convertible Crossbody • Cynthia Rowley • Sold Out
Women’s Adidas ‘Stan Smith’ Sneaker • adidas • $60

Who says jewel tones aren’t for the warmer months?! Pairing a jewel-toned dress or skirt with a neutral sweater is a fabulous way to embrace color in your wardrobe. A jewel-toned skirt also translates well for fall.

J.Crew – Cashmere Sweater – Gray • J.Crew • Sold Out
Barena full midi skirt • Barena • Sold Out
Spitfire FTL in Green. • Spitfire • $33
Gucci Black Princetown Slip-On Loafers • Gucci • Sold Out
Lancaster Paris Pur & Element Saffiano Leather Bucket Bag • $240

Try finding a skirt with interesting details like contrast piping or stripes. Keep it casual with sneakers and your favorite light and cozy sweater. You’re all set for a day of running errands or shopping around!

Vince – Textured Stretch Merino Wool-blend Sweater – Black • Vince • Sold Out
Vince Camuto Striped Pleated Skirt • $74.99
Women’s Adidas ‘Stan Smith’ Sneaker • adidas • $60
Cult Gaia Mini Acrylic Ark Bag • $280

Date night gets a relaxed make-under with a sweater, skirt, and ankle boots. Throw on a skirt (metallic if you’re brave!) and heeled boots and you’re ready to go. A basic bag with pronounced hardware is the only accessory you need!

Chloe Drew Leather Shoulder Bag – Black • Chloé • $1,850
J.Crew – Cashmere Sweater – Camel • J.Crew • Sold Out
Alice+Olivia midi pleated skirt • Alice + Olivia • Sold Out
Barneys New York Women’s Suede Ankle Boots • Barneys New York • $425

This might be my summer staple look. A nearly floor-length dress works well for day wear with flat sandals and a thin sweater.

3.1 Phillip Lim – Ruffled Pointelle-knit Sweater – Midnight blue • 3.1 Phillip Lim • Sold Out
Suno pleated skirt • Suno • Sold Out
Women’s Madewell Winking Hinge Cuff • Madewell • Sold Out
Women’s Steve Madden Jole Embellished Slide Sandal • Steve Madden • $34.96
Kenneth Jay Lane Polished Hinged Open Bangle Bracelet • Kenneth Jay Lane • $25

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Image sources: 1 / 2 / 3 / 4 / 5 / 6 / 7

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