20 Under $100 Jackets to Wear With Dresses

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Collage Vintage

As the weather gets progressively colder, we officially transition to comfy winter clothing. There's something so exciting about breaking out that favorite jacked, ankle booties, and chunky scarves. But don’t pack up those warm-weather pieces quite yet: With the right clothing and accessories, your favorite dresses can easily adapt to the next season. Here, we discuss the best jackets to wear with dresses this season all under $100. From plaid blazers to puffers and more, these affordable options are a guarantee way to reinvent your favorite dress this winter. To help, we've rounded up some of the best street style moments to share the key styling tips to help master this tricky transition.

Below, we reveal the best under $100 jackets to wear with dresses.

BOMBER JACKET

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Collage Vintage

Looking for a seamless way to add an athleisure piece to your wardrobe? Look no further than the bomber jacket. Style a silky bomber over a midi dress with sneakers. 

An oversize bomber jacket is ideal for layering.

Available in sizes 0 to 12. 

Wear a leather bomber jacket over a white tee. 

Available in sizes S to 4X

Try this military-green bomber jacket. 

Available in sizes S to L. 

Wear black booties and vintage denim with this jacket. 

Available in sizes S to L. 

PUFFER JACKET

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Collage Vintage

A puffer jacket is a guaranteed way to keep warm this winter, even on the coldest days. Wear an oversize bomber with a minimalistic slip dress. 

Style an oversize puffer jacket with a slimming slip dress. 

Available in sizes 2 to 16. 

A puffer jacket is a guaranteed way to stay warm this winter. 

Available in sizes XS to L. 

Try this feminine shade. 

Available in sizes 14 to 28. 

An easy way to take on the sportswear trend.

Available in sizes XS to XL. 

PLAID BLAZER

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Collage Vintage

Menswear is having a moment this year. For the office, wear a plaid blazer with a tailored dress and kitten heels. Then on the weekends, play with patterns by wearing the blazer with a floral dress.

Menswear remains a huge trend in the fashion world. 

Available in sizes 0 to 12. 

An office-appropriate option. 

Available in sizes X to 4X. 

Style a plaid blazer with minimalistic dress and sneakers. 

Available in sizes S to L. 

A blazer is a quick way to elevate your outfit.

Available in sizes XS to L. 

DENIM JACKET

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Collage Vintage

The denim jacket is hands-down a fashion essential. Try buttoning half your jacket and wearing it off one shoulder. 

Style a denim jacket with jeans for a retro look. 

Available in sizes XS to L. 

An oversize denim jacket is a key layering piece. 

Available in sizes XS to L. 

Opt for a bright color. 

Available in sizes 2 to 12. 

Wear your favorite denim jacket with a graphic tee. 

Available in sizes S to L. 

MOTO JACKET

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Collage Vintage

The moto leather jacket is incredibly versatile. Wear a black style with a statement dress and minimalistic accessories. 

Bold red is having a moment this season.

Available in sizes XS to XXL. 

Patent leather is having a moment this year. 

Available in sizes XS to L. 

Your new going-out jacket. 

Available in sizes XXS to XL. 

A leather jacket is a fashion-girl essential. 

Available in sizes 12 to 20. 

Now, check out the best affordable boots everyone is buying this season.