Best Casual Maxi Dresses

There are four reasons I love casual maxi dresses. One, they are great for airplanes. They don’t cut into your stomach like a non-stretchy jean, and they keep your legs warm. Two, they can be dressed up (like I did in the outfit above) and down. You can wear a casual maxi dress to both the grocery and a summer party. Three, you don’t have to shave your legs. Four, the length protects your legs from the sun. I love to prevent sun damage, but I know we aren’t always good about putting on sunscreen. With that said, below are some tips on how to wear a casual maxi dress, but if you are ready to shop, scroll on down to my favorite casual maxi dresses I have put on my clients and myself this month.

How To Wear A Casual Maxi Dress: The Shoes

Here are the best shoe options for your casual maxi dresses…

1. Flat Sandals
2. Low Chunky Heels
3. Open Toe Wedges

Basically, you want to skip anything closed-toed. There are exceptions of course, especially in the winter when the right bootie can look quite cool with a long sleeve maxi dress. But if we are talking casual maxi dresses in the summer, which are usually sleeveless, do me the pleasure of sticking with these open-toe options. You also want to skip those stilettos.

How To Wear A Casual Maxi Dress: The Outerwear

Here are the three best outerwear options for a casual maxi dress…

1. Rectangular Scarf aka A Shawl: Shawls are an elegant accessory that can add warmth when needed and be shoved into your purse, or hang loosely around your neck when you don’t need them. Make sure your shawl has a similar texture and flow as your casual maxi dress. For example, don’t mix a shiny shawl with a matte linen dress. For tips on how to tie and style a shawl check out this post.
2. Cropped Jacket in Denim or Leather: Be careful if you choose a cropped denim jacket. Skip the denim with contrasting orange thred or robust pockets on your bust. Also, skip the overly cropped, aka shrunken, denim jacket — that’s dated. You want a relaxed, but flattering modern version of the timeless denim jacket. Also, keep in mind that you want to pair a dark denim jacket with darker maxi dresses, and lighter denim jackets with lighter maxi dresses. Don’t create too much contrast. If you’re looking for a slightly edgier option, a mid-weight waist-length supple leather jacket is perfect with a casual maxi dress. Just make sure it is not too stiff or heavy. That looks disjointed over the flow of a fabulous maxi dress.
3. Fitted Cardigan of Any Length: A cardigan that drapes beautifully down your body is one of my favorite choices for a casual maxi dress. If it hugs your body beautifully, any length can work, from waist length to floor length. Just make sure to skip any grandpa or baggy cardigans. This is not the best look with a casual maxi dress, unless it is a body-con maxi dress.

Farm Rio Tie-Front Linen Dress

Sizing + Fit: XXS-XL

Fabric: Linen; cotton lining

Caslon Sleeveless Jersey Maxi Dress

Sizing + Fit: True to size. Comes in sizes XXS-XXL

Fabric: 95% rayon, 5% spandex

A.L.C. Rhodes Cotton Maxi Dress

This casual maxi dress is available at Bloomingdale’s, Nordstrom, and Shopbop.

Sizing + Fit: Order your true size and a size up to compare. Comes in sizes 00-14.

Fabric: 100% cotton

Farm Rio Pineapple Garden Maxi Dress

This maxi dress is available at Bloomingdale’s, Anthropologie, and Saks Fifth Avenue.

Sizing + Fit: True to size. Comes in sizes XXS-XL.

Fabric: 100% viscose

Aqua V-Neck Maxi Dress

You may need to tailor the top of your bust like I did. A good tailor can easily do this and then the fit will be perfection.

Sizing + Fit: True to size. Comes in sizes XS-XL.

Fabric: 55% linen and 45% rayon; lining 100% rayon

Elan Sleeveless V Neck Maxi Dress

This casual maxi dress is available at Bloomingdale’s and Amazon.

Sizing + Fit: Order your true size and a size down to compare. Comes in sizes XS-XL.

Fabric: 100% rayon

Aqua Cotton Sleeveless Eyelet Cutout Maxi Dress

Sizing + Fit: True to size. Comes in sizes XS-XL

Fabric: 100% cotton; lining 100% polyester

Karen Kane Jersey Knit Maxi Dress

This maxi dress is available at Bloomingdale’s and Nordstrom.

Sizing + Fit: True to size. Comes in sizes XS-XL.

Fabric: 92% rayon, 8% spandex

Farm Rio Leopard Forest Midi Dress

This summer dress is available at Bloomingdale’s, Neiman Marcus, Nordstrom, and Saks Fifth Avenue.

Sizing + Fit: True to size. Comes in sizes XXS-XL.

Fabric: 100% cotton

Nordstrom Mixed Media Tank Maxi Dress

Sizing + Fit: True to size. Comes in sizes XXS-XL.

Fabric: 93% cotton, 7% spandex

Bleu by Rod Beattie Let’s Get Loud Floral Print Cover-Up Maxi Dress

This casual maxi dress is available at Nordstrom, Zappos, and Bleu by Rod Beattie.

Sizing + Fit: S-L

Fabric: 100% rayon

Loveappella V-Neck Jersey Maxi Dress – Hazelnut

Sizing + Fit: If between sizes, order one size down. Comes in sizes XS-XL and petite sizes.

Fabric: 95% rayon, 5% spandex

Loveappella V-Neck Jersey Maxi Dress – Dark Purple

Sizing + Fit: If between sizes, order one size down. Comes in sizes XS-XL and petite sizes.

Fabric: 95% rayon, 5% spandex

NZT by Nic+Zoe Scoop Neck Linen Blend Tank Dress

This casual maxi dress is available at Nordstrom and Nic + Zoe.

Sizing + Fit: True to size. Comes in sizes XS-XL

Fabric: 52% linen, 48% rayon

Reformation Rou Dress

This Reformation Rou Dress is super soft, has pockets, and doesn’t require wearing a bra. It also comes in a variety of colors.

Sizing  + Fit: Runs small, order one size up. Comes in sizes XS-XL.

Fabric: 88% Tencel lyocell, 12% spandex.

Casual Maxi Dresses From Years Past

I originally wrote this post years ago and update it regularly due to its popularity. I’ve left these photos below for nostalgic purposes. Whenever I update older posts, I love to hold on to a collection of images as a bit of a time capsule so we can watch how our style evolves.

Bailey 44 Dishdasha Dress

This Bailey 44 Dishdasha Dress is the perfect airplane dress. The ruching is forgiving and the style can go from a Padres game to a concert. This dress is available at Nordstrom and Neiman Marcus.

Sizing Tip: Runs a bit small. Order a size up.

J.Crew Ratti V-Neck Maxi Dress

The J.Crew Ratti V-Neck Maxi Dress is really beautiful and 100% cotton. Of all the casual maxi dresses on this list, this is the dressiest, but that doesn’t mean you can’t wear it more casually. Yes, you can wear it to a wedding, but you could also wear it to a barbecue with the right crowd. And nothing would stop me from wearing this for rooftop drinks.

Sizing Tip: True to size, but also order a size down to compare if you’re unsure.

Stone Row Addicted 2 Me Smocked Maxi Dress

I adore this Stone Row Addicted 2 Me Smocked Maxi Dress. The print is absolutely fresh and the comfort is spot on. Wear this to brunch, parties, the Del Mar Races, and the pool. If you don’t like the sleeves, you can seam rip them off, but I think they make the look.

Sizing Tip: Runs true to size, but I recommend also ordering one size up to compare.

Felicity & Coco Strapless High/Low Dress

This Felicity & Coco Strapless High/Low Dress is silky soft, flattering, and fun. I could wear this to any social event.

Sizing Tip: True to size, but also order a size down to compare.

Red Carter One-Shoulder Maxi Cover-Up Dress

The Red Carter One-Shoulder Maxi Cover-Up Dress is very high cut. It goes great over a swimsuit, but I love it as a dress. I envision you wearing it as a hostess when you have people over at your home. I promise it’s not too see-through.

Sizing Tip: One size fits most, so it works like a mumu.

Tart Chloe Empire Waist Maxi Dress

Tart makes yummy maxi dresses and this Chloe Empire Waist Maxi Dress is no exception. Their fabric is pajama soft, but not thin, and their cuts are flattering.

Sizing Tip: Runs true to size, but also order a size down if you want to compare.

MICHAEL Bloom Maxi Dress

This MICHAEL Michael Kors Bloom Maxi Dress is so sweet and versatile. You can wear this to the grocery or a party. It is available at Nordstrom, Bloomingdale’s, Dillard’s, Zappos, and Macy’s.

Sizing Tip: Runs very large. Order 1-2 sizes down.

Maeve Elseby Lace-Up Dress

You may recognize this Maeve Elseby Lace-Up Dress from my What To Wear Wine Tasting post. It is crazy soft, has a heftiness to it that I like, and you don’t have to wear a bra — it does amazing things for the bust.

Sizing Tip: Runs true to size. As a size 6 woman, I wear a small. Keep in mind that the ties in the back make it a little adjustable too. At first, I thought the small was too small for me, but it absolutely wasn’t. It’s perfect.

BP. V-Neck Casual Maxi Dresses

This BP. V-Neck Maxi Dress is inexpensive, soft, and flattering. In fact, BP always puts out awesomely soft and affordable casual maxi dresses. Click here to check out more.

Sizing Tip: True to size.

Lacausa Molly Midi Dress

I love this Lacausa Molly Midi Dress for its bold color, pockets, and breast support. I have been wearing it with the SOFTEST jean jacket ever: Pilcro Boyfriend Denim Trucker Jacket. Note, this jacket is oddly sized. I wear a small petite in it. The regular small was too wide and long, but the XS was tight on my upper bicep. SP for the win!