Shop Under-$50 Dresses to Wear With Ankle Boots This Fall

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While it’s easy to find stylish dresses in the hundreds (even thousands) these days, it’s always refreshing to come across a few that you love without the chill-inducing price tag. At least, I feel that way, and lately, I’ve been getting the sense that we’re on the same page, which is why I thought you guys would too.

Seeing as fall is right around the corner, I figured it might be the perfect time to round up such frocks (and, of course, jumpsuits) so that you can make your life easier and style them with ankle boots all season long. From bold florals to of-the-moment animal prints to flattering stripes and of course a few utility-inspired ones, simply continue on to shop the best under-$50 dresses and jumpsuits from our Who What Wear collection right now.

Who What Wear x Target

Long Sleeve Asymmetric Hem Midi Shirt Dress

Also available in more sizes.

Who What Wear x Target

Long Sleeve Wrap Midi Dress

Also available in more sizes.

Who What Wear x Target

Sleeveless Button Knit Midi Dress

Also available in more sizes.

Who What Wear x Target

Long Sleeve Utility Jumpsuit

Also available in more sizes.

Who What Wear x Target

Puff Sleeve Midi Dress

Also available in more sizes.

Who What Wear x Target

Floral Print Smocked Waist Dress

Also available in more sizes.

Who What Wear x Target

Floral Print Short Sleeve Smocked Waist Dress

Also available in more sizes.

Who What Wear x Target

Polka Dot Short Flutter Sleeve Midi Dress

Also available in more sizes.

Who What Wear x Target

Leopard Print Long Sleeve One Shoulder Midi Dress

Also available in more sizes.

Who What Wear x Target

Short Sleeve Denim Midi Shirt Dress

Also available in more sizes.

Who What Wear x Target

Short Sleeve Wrap Midi Dress

Also available in more sizes.

Who What Wear x Target

Short Shirred Sleeve Dress

Also available in more sizes.

Who What Wear x Target

Long Sleeve Midi Dress

Who What Wear x Target

Floral Print Ruffle Placket Midi Dress

Also available in more sizes.

Who What Wear x Target

Polka Dot Sleeveless Ruffle Midi Dress

Also available in more sizes.

Who What Wear x Target

Short Pleat Sleeve Midi T-Shirt Dress

Also available in more sizes.

Who What Wear x Target

Puff Sleeve Midi Dress

Also available in more sizes.

Who What Wear x Target

Apron Neck Jumpsuit

Also available in more sizes.

Who What Wear x Target

Long Sleeve Wrap Midi Dress

Also available in more sizes.

Up next? Our favorite boot brands to wear with all these dresses, naturally.

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Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.