3 Effortless Shirtdress Styles That Go From Casual to Chic

affordable Shirtdresses Cloth & Stone 55

I like my clothing the same way I like my beauty products – versatile and effortless – which brings me to one of my wardrobe favorites – the shirtdress.  This can be anything from a tee or tank-turned-dress, or a classic button-up with more masculine (but still sexy) vibes.  Have two or three in your closet, and you’re set for everything from summer BBQ’s and Sunday brunches, to work and happy hour.

When you open those closet doors and grab one off the hanger, there’s no thinking involved.  You don’t need to pick out a pair of pants to match, or skirt – just slip it on and head out the door.  Plus, you can easily dress them up or down simply by switching out your shoes and accessories.  For example, for a casual look, pair a shirtdress with sneakers and a baseball cap.  Then, for a night out, swap them for some heels/boots, jewelry, and a sophisticated little handbag for a classy-chic look.  Here are three shirtdress styles that offer a ton of flexibility…

The T-Shirt Dress

If you have yet to introduce the shirtdress to your closet, the first one I’d recommend picking up is a basic black tee shirt dress.  It makes for the perfect blank canvas to dress up or down, and transitions effortlessly from day to night, filling in the ‘little black dress’ role when you need it to.  I recommend going for one that’s on the looser side (think shift dress) instead of skin-tight, with a v-neck.  The looser fit gives it more casual vibes, and when you want to dress it up, you can simply add a skinny belt to pull it in while adding some interest.  For a budget-buy, Boohoo has a cute oversized one for only $24, and Pretty Little Things has one here for $12.  I also love Daily Ritual’s dresses – they’re super soft (and also very affordable), and have a curvier shape than your average t-shirt dress while still leaving some wiggle room.

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The Button-Up Shirtdress

Another must-have is the belted shirtdress.  They just look so chic and effortless, and pair beautifully with casual flats and loafers, all the way to stiletto heels.   J.Crew makes some of my favorites.  For example, I’m loving this knit one – it falls right at the knees, so it’s perfect for the office, but would also work perfectly for a Sunday brunch.  And for something just a tad more casual, I’m loving this sleeveless chambray shirtdress.  Pair it with a cardigan for a casual Friday look at the office, or wear it on your beach vacay layered over your bathing suit!  Ivanka Trump also makes a sophisticated little ivory dress that you could wear practically everywhere!

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The Plaid Shirtdress

And finally, the third must-have style is the more casual plaid button-up shirtdress.  All of the styles I mentioned earlier can be layered up for fall, but plaid shirtdresses are my favorite as they pair especially well with jean and leather jackets and knee-length boots for an extra edgy look.  Jack by BB Dakota has some classy-looking ones in lighter colors like ivory and pale blue that would be perfect for summer with some heels or sandals and a skinny belt.  And if you’re looking for some darker plaids for fall and winter, Obey has both black and deep red ones that would be perfect for pairing with black tights or suede knee-high boots, and a fall jacket or winter coat.

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Plaid Shirtdress Cloth & Stone 43

The one I’m wearing here is from Cloth & Stone (which I managed to find over at thredUP for a steal!).  Since the weather is still warm, I simply paired it with some stud earrings (a find from my last Trunk Club box) and my favorite block heel sandals from M.Gemi (reviewed here) and was set!  The sandals add a little pizazz, but also tie in perfectly with the more down-to-earth, relaxed vibes of the dress.

m.gemi the attrice sandals 006

Stacked heel sandal from M.Gemi (similar)

M.Gemi has some of the classiest looking shoes, plus they’re extremely well made and comfy.  If you’re on the hunt for some last-minute summer sandals or shoes for fall, definitely check them out!


Are you a fan of the shirtdress? What’s your favorite style and way to wear them?

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