When we think of dresses, the first thing that usually comes to mind is getting dressed up for a party, wedding, or other semi-formal event. Thinking about going dress shopping normally involves trying on short and sleek cocktail dresses or A-line party dresses. But what if you’re looking to kick back and take it easy? Normally wearing a dress doesn’t seem like the choice for a laid-back casual day, but I’m here to change your mind!

These gorgeous options are perfect for casual weekends and day looks. I’ll show you dress options that are perfect to wear running errands, to a backyard barbecue, to a casual summer concert, and even comfy looks that are perfect to wear traveling or on vacation. In fact, there is a whole page of casual dresses that are perfect for all your days of dressing down. Slip into one of these cute casual dresses and add a polished look to your casual daywear.

Contrasting Cool


OK, so the first one is not technically a dress, but I wanted to include it anyways. This is one of those great outfits that is super easy to toss on but still makes you look chic, polished, and put-together. I can see this maxi skirt being worn on vacation or to the airport while traveling. It’s also a great skirt to pair with any tee or top for a casual day look when you’re out running errands but don’t want to look like a total bum. If it’s a bit cooler outside, you can easily toss a fitted denim jacket over the top to create a polished put-together look.

I also love the contrast of chic neutrals paired together. Solid black paired with beige is particularly striking. The free-flowing floor-length maxi skirt has that laid-back bohemian effect, complete with a waistband of stretchy crochet knit. Add to that a lining that reaches down to mid-thigh and it creates a sheer, gauzy effect. Here is a great cropped black tee if you want to create a similar outfit.

Casual Stripes

Since we’re on a black and beige kick, let’s continue with the next neutral look! The key to casual dressing is to find things that look polished and put-together but are still comfy. This black and beige striped dress checks all the right boxes. Stripes are a wardrobe staple we love and the lace trim at the neckline adds a girly touch. The cinched drawstring waist and cotton fabric keep this little number cute and comfy. This is just one of those great wardrobe staples to have on hand when you have to run out to the store or to the post office and you don’t want to spend an hour getting ready, but you don’t want to look like a bum either. Toss it on alone or with a black cardigan and some basic black sandals and you’re out the door in 5 minutes flat. On sale for just $14, now is the time to add this to your wardrobe!

Sporty Spice

What I love about this next neutral look is the sporty feel of this striped dress. Whether you’re a baseball fan heading to a Chicago White Sox rooftop party or you’re taking in a tennis match at the US Open, wearing this dress will give you the chic and polished look you’re after while still maintaining that laid-back sporty vibe. The pinstripes remind us of America’s favorite pastime (baseball!) but the flowy A-line cut is perfect for on or off the tennis court. When game day rolls around, I’m always on the lookout for something a little more polished and girly than the typical frumpy jeans and a t-shirt look everyone wears. This dress will stand out without looking like you overdid it. This sporty dress is a WIN- whether your team does or not! In order to keep it sporty and casual, try pairing it with black sandals or black and white Converse style tennis shoes.

Tee Time

What’s better than your favorite classic t-shirt? Maybe this cute and casual navy dress with a classic cut like your favorite fitted t-shirt. When the weekend rolls around, instead of throwing on a bummy tee and jeans that will stifle you, throw on this cute and comfy A-line dress made of a casual cotton fabric similar to a comfy t-shirt. The best part of it is that it has that classic cut, but the girly lace details at the sleeves and bust keep you looking chic. You won’t sacrifice comfort, but you’ll look 10 times more chic and sophisticated while you’re out running errands or meeting up with friends. I can see this being worn with beige wedges or sandals. Also available in Off White.

That’s a Wrap


When we think of casual dresses, the classic wrap dress always comes to mind. The wrap style was first created by Diane Von Furstenberg in the 1970s and became a huge hit with working women for its ease and simplicity. The wrap style effortlessly creates a polished put-together day look with minimal effort. Slip into this feathery light wrap number and you’d swear you’re floating on air. Yes, seriously! Made of soft flowy chiffon, the fabric is designed to waft around your curves in the most natural way. The delicate shape similarly mirrors this relaxed vibe – a V-neckline and soft cap sleeves create a snug and cozy fit on the bust area. This leads into a fitted waistline, defined beautifully by a thin fabric belt. This is a casual day dress you can wear to work in an office setting and then out to dinner or drinks afterwards. Also available in Powder Blue.

Country Cutie


How can you not melt at the idea of a strapless dress in a shade of delectable butter? This Expertly Embroidered Mesh Strapless Dress has all the makings of a casual classic. The shape is sweet and girly, fitted across the bust and midriff before leading into a full A-line skirt. The entire dress is fully lined but the lower half is slightly sheer just so that you can still make out the embroidered designs on it. I love that the embroidered designs give it laid-back casual country look. I can see this dress being worn with cute cowboy boots to a country concert or festival. It could also be dressed up a bit and worn as a bridesmaid or rehearsal dinner dress. It’s the perfect option for a more casual country style wedding in a barn or other laid-back venue. Also available in Pink Coral.

A Bright Burst of Florals


What woman doesn’t love the surprise of a huge bunch of flowers? Here we have a structured A-line dress just covered in them! In shades of beautiful bright pink, olive green and pure white, the overriding effect is sweet and unabashedly feminine. Thin adjustable spaghetti straps dance over the shoulders while a defined sweetheart neckline is highlighted by hot pink buttons all down the bust area. There’s even a fabric sash that wraps around the waistline for an even more defined hourglass silhouette. Pair it with some beige wedges to complete the look. Wherever you wear this girly gem, you’ll be the talk of the town!

Sky Blue Stunner


Another flowery must-have – only this time it’s the fine pairing of sunny sky blue and brilliant white. This Flower Patch Embroidered Strapless Dress reminds us of a relaxed day walking in the countryside or strolling along an untouched beach. The gorgeous pale blue shade is embossed with finely embroidered flower motifs making up its hemlines. Wear this one with your favorite casual flat sandals for an easygoing summer ensemble. Also available in Pink or Yellow.

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