Can You Wear Booties With a Midi Dress

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Dress: Madewell

Necklace: similar here

Boots: similar here

Lips: NARS "Dragon Girl"

Bag: c/o Paravel

Winter time and jeans go hand in hand. I mean, I get it. It's cold. My legs are freezing so I have to keep covered. But sometimes aren't you just sick of the denim? One of the reasons I love springtime so much is that I get to break out my favorite sundresses. So why not wear them now!? We'll have to make some modifications, of course. This isn't the time to break out a crop top! Today I'm showing you how to style a midi dress with ankle boots for winter, and let me tell you, it's quickly becoming one of my favorite looks!

How To Style A Midi Dress With Ankle Boots - Poor Little It Girl

How To Style A Midi Dress With Ankle Boots When You Are Petite

The second this red ruffled midi dress showed up on my doorstep I knew I had to wear it out immediately. But yes, it was a little cold out. So while in the springtime I'll be wearing this one with sandals and a straw hat, for winter, It was all about the boots.

Now let me preface I was definitely chilly taking these photos but I didn't want to wear my coat. I really wanted you to see how gorgeous the color and print of this dress was…so I braved a few freezing minutes. Hey, that's what blog life is all about!

Accessorizing a Midi Dress

I don't think I've ever tried doing a midi dress and ankle boots before, but I am obsessed with this look.  It feels very New York City cool girl chic, right? And yes, if it was colder out, I totally would have worn black opaque tights with this. But I didn't think it was necessary today. I mean, it was cold but nothing I couldn't handle.

Obviously, with this midi dress and ankle boots look, I wanted to keep my accessories pretty minimal. I really want the dress itself to be the centerpiece! This neutral bag is so fun and unique and my long necklace kind of goes with the boho vibes of the entire outfit. And uh, like I could possibly wear a red dress without adding on a bold red lip. It's required, right?

With solid color or a more neutral dress, you obviously have a little room to experiment with accessories. In that case, I would definitely add a fun, bright colored bag or statement earrings. Color and statement pieces are a great way to add a little interest to your look. It may be gray outside during the winter months, but that doesn't mean you always have to wear muted colors to match!

Red Madewell Dress - Poor Little It Girl

Proportions and Balance for a Midi Dress

One of the reasons I was excited to share this look with y'all as well is that I feel this is a great look to inspire my fellow petite ladies. Usually, you hear a lot of short women like myself say that they can't wear midi hemlines or ankle/low calf boots but yes, yes you can! Any body type can pull off this length skirt or dress, and any body type can wear ankle boots. It's all about proportions and balance!

If you're curvy, you might opt for a fuller midi skirt or dress that sits at your natural waist and skims your hips. If you have more of a straight frame, you could opt for something a little more fit and flare.

Ideally, a midi dress/skirt should hit mid calf. For those of you with a little more height than I have, this usually isn't an issue. For those of us on the petite side, though, it's something we need to be aware of. We don't want our midi dress to end up falling somewhere between midi and maxi! This midi dress actually hits a few inches above where the boots start, so I'm still creating a long line with the eye, which elongates my legs. Yes, please!

Styling with Ankle Boots

For me, the ankle boots solidify this as a winter look. I mean, we wait all year to pull out our boots, so let's wear them! I tend to like wearing a midi skirt with heeled shoes to add a little extra height and length. You could certainly wear a flat boot instead.

I'll likely stick stick with these heeled ankle boots throughout the winter months to keep my feet warm, but if you live in a warmer climate (like Florida) you could definitely switch this up. A pair of classic pumps or slightly lower ankle booties would be great options for this dress. Or, if the dress is a little more casual than this one, you know I love wearing a pair of white sneakers!

How To Style A Midi Dress With Ankle Boots - Poor Little It Girl

I'm no stranger to the midi dress or midi skirt. In fact, I've featured this length several times before! If you want to see how I've styled this look in other seasons, take a look at how I styled a midi pencil skirt and chunky heel for spring, or this super cute red polka dot midi skirt for summer. And again, just to emphasize that anyone of any shape or size can wear a mid-length skirt or dress, I wore this solid color, form fitting midi-dress on a constant rotation throughout my pregnancy.

If you want to get more of my petite styling tips, make sure you check out my complete Petite Fit Guide!

PHOTOS BY SYD & LEX PHOTOGRAPHY
  • Poor Little It Girl™ partners with affiliate programs, meaning that I can earn a commission from purchases/clicks by those who visit this site at no additional cost to you!

  • Dress: Madewell

    Necklace: similar here

    Boots: similar here

    Lips: NARS "Dragon Girl"

    Bag: c/o Paravel

    hawkinstheyet.blogspot.com

    Source: https://www.poorlittleitgirl.com/how-to-style-a-midi-dress-with-ankle-boots/

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