25 Flattering Dresses You Can Wear Anywhere This Fall, Winter, and Beyond

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Every time I buy a new dress, I think to myself, "OK, that's it, no more." Somehow, a week later, I fall in love with a new one I "need" again, which can be especially dangerous for my bank account with gifting season right around the corner. Currently, my obsession revolves around Banana Republic's Fall and Winter dress selection. The store has so many beautiful choices that are great for work, the weekends, and all those fancy holiday events. So if you're looking to spruce up your wardrobe without draining your funds, you've come to the right place; these options start at $99.

To save you valuable time, I curated a list of my 25 favorite picks of the season that the retailer has to offer. With cozy sweater dresses that will keep you equally warm and stylish, metallic ones you can wear while ringing in the new year, and even one that's been duchess of Sussex-approved, there's no shortage of good finds ahead. Keep reading to shop them all and find your next holiday look (or an entire wardrobe's worth).

Additional reporting by Krista Jones

Chunky Turtleneck Sweater Dress
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Chunky Turtleneck Sweater Dress

The color, texture, and style of this Chunky Turtleneck Sweater Dress ($159) nails the trifecta needed for a cozy-yet-chic Winter piece.

Puff-Sleeve Wrap Dress
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Puff-Sleeve Wrap Dress

Step into your next holiday party wearing this red Puff-Sleeve Wrap Dress ($129), and you're guaranteed to turn every head in the room.

Metallic Dot Tie-Neck Dress
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Metallic Dot Tie-Neck Dress

This Metallic Dot Tie-Neck Dress ($139) strikes the balance between comfortable, casual, and easy to dress up if and when you want to.

Peasant Midi Dress
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Peasant Midi Dress

It looks like leopard print is here to stay, so show off your playful side with this long sleeve Peasant Midi Dress ($159).

Luxespun Turtleneck Dress
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Luxespun Turtleneck Dress

Comfortable and undeniably stylish, this Luxespun Turtleneck Dress ($119) will be an incredible addition to anyone's wardrobe.

Double-Breasted Trench Dress
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Double-Breasted Trench Dress

If you think this Double-Breasted Trench Dress ($139) looks familiar, you're 100 percent correct. Meghan Markle was spotted in this exact dress recently, so grab this if you want to channel her style this Fall and Winter.

Flutter-Sleeve Midi Dress
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Flutter-Sleeve Midi Dress

You can never have too many black dresses, so add this Flutter-Sleeve Midi Dress ($129) to your rotation for a little added flair.

Print Midi Shirt Dress
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Print Midi Shirt Dress

This Print Midi Shirt Dress ($169) is as versatile as it is playful; it's simple to style for work or weekends alike.

Ribbed Mock-Neck Mini Dress
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Ribbed Mock-Neck Mini Dress

This Ribbed Mock-Neck Mini Dress ($99) is the perfect everyday piece and will make you look put together even on the laziest of days.

Metallic High-Low Dress
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Metallic High-Low Dress

Shiny, sparkly, and just the right amount of glam, this Metallic High-Low Dress ($159) is one of Banana Republic's best dresses for holidays and New Year's Eve events.

Print Maxi Shirt Dress
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Print Maxi Shirt Dress

This Print Maxi Shirt Dress ($149) is the perfect piece to introduce giraffe print into your wardrobe.

Turtleneck Column Dress
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Turtleneck Column Dress

Easy to pair with boots or a blazer (or both), this Turtleneck Column Dress ($129) comes with endless styling options.

Metallic Leopard Bi-Stretch Sheath Dress
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Metallic Leopard Bi-Stretch Sheath Dress

This Metallic Leopard Bi-Stretch Sheath Dress ($129) is made from a fabric that will keep you comfortable all day (or night) long.

Print Wrinkle-Resistant Wrap Dress
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Print Wrinkle-Resistant Wrap Dress

This Print Wrinkle-Resistant Wrap Dress ($99) is giving us major equestrian vibes, which means it'll never go out of style.

Print Soft Ponte Ruffle Mini Dress
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Print Soft Ponte Ruffle Mini Dress

If the print and vibrant red shade weren't bold enough, just add a ruffle to stand out in this Print Soft Ponte Ruffle Mini Dress ($129).

Lace Sheath Dress
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Lace Sheath Dress

A Lace Sheath Dress ($149) is a total wardrobe staple; you can wear and rewear it countless times, all year round.

Ribbed Sweater Dress
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Ribbed Sweater Dress

The warm-toned camel shade of this Ribbed Sweater Dress ($139) will flatter any skin tone.

Print Utility Popover Shirdress
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Print Utility Popover Shirdress

This Print Utility Popover Shirtdress ($129) is lightweight and comfortable, making it ideal for those days where you just don't feel like wearing pants.

Floral Puff-Sleeve Dress
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Floral Puff-Sleeve Dress

If you're already counting down the days to Spring, this pretty Floral Puff-Sleeve Dress ($139) might make cold days feel a little more bearable.

Striped Luxespun Turtleneck Dress
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Striped Luxespun Turtleneck Dress

Slip into this Striped Luxespun Turtleneck Dress ($119) when you want to feel warm and cozy, but still put together.

Metallic Dot Mini Dress
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Metallic Dot Mini Dress

You don't need to go full glitz to feel glam for the holidays, and pieces like this Metallic Dot Mini Dress ($139) are proof.

Wrinkle-Resistant Wrap Dress
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Wrinkle-Resistant Wrap Dress

Although it's simple, this marsala-colored Wrinkle-Resistant Wrap Dress ($99) is the perfect easy staple in anyone's wardrobe. The under-$100 price tag makes it one of Banana Republic's best deal dresses, too.