3 Fresh Ways To Style An Essential Shirtdress

A highly versatile blank canvas, a shirtdress can take you from day to night and back. First gaining popularity in the '40s, this is a piece that should exist, in some incarnation, in the wardrobes of every style-conscious woman in 2011. I recommend the shirtdress to a lot of my Haute Closet clients, be it a specimen by The Row, as shown here, or something from American Apparel, DVF, vintage, or better. It can be forgiving, always feminine, and tough enough to stand up in a boardroom. Buying a well-made, high-quality basic like this one will prove its worth in no time. When I walked into Chalk and saw this piece from The Row’s Pre-Fall 2011 Collection, it was a gift for our collective all-season wardrobe and a god-send in the realm of basics. With its slightly flared skirt and exquisite tailoring, the garment has a delicious bit of stretch and a barely there sheen allowing it to transform seamlessly into the closets and onto the bodies of very different women.

1. Belt: Belts hitting the natural waist remain a mainstay in the stylish woman’s wardrobe. They can be cheap or expensive, beaded, chain, leather, or ribbon—stock your arsenal because you can wear them. A lot. My friend Swathi was taking a trip to see her beau, so I riffed on train rides and hopeless romantics to give the dress sartorial sweetness. Belts are the most obvious accessory for a shirtdress; really the only way to define the waist. Here, the pretty bow-belt is given edge by the combined textures of the bag, shoes, and the intricate necklace.

2. Bolster: With a well-chosen hat, bag, or shoe, you can totally transform your look. Either a straw fedora or a fascinator, flip-flops, or jewel-encrusted pumps, a great shirtdress can carry them all. When I imagined the dress for an easy-going beauty like Hilary, I thought playful and pragmatic, on the street and at the office. Even though it’s been dreadfully hot, A/C can be incredibly cold. Here, the shirtdress works as a jacket and a buffer against the breeze. Worn over a pretty summer dress, the Nike high-tops keep it fun and make it casual while the ladylike accessories make it anywhere-appropriate.

3. Layer: Even if you leave the dress open, you can vary the look and fullness of its skirt by adding an underskirt that hits just above or below the hemline of the dress. Otherwise, use the shirtdress as a topper or jacket and play with proportions on top and underneath. As one of the coolest ladies I know, I made sure to give Christina her due with an edgy look designed to turn heads and take on the town. Dressing up her own C/FAN skirt with a tough little bustier, these chevron-stripe and flouncy silk pieces were mimicked by the shape of the boot and the positioning of the dress on top. And with the added rocker accessories, this look can go to dinner, drinks, and a show, no sweat.

You can wear just about every accessory in your closet with a shirtdress and a little creativity: The dress can be buttoned all the way up or all the way down, the belt can be of any material, the shoes can be substituted, the list goes on and on. The most important thing to remember when choosing a shirtdress is less is best. The perfect specimen will be devoid of extras like ruffles and attached belts and should always button all the way down. Prints are okay if it’s one that doesn’t need to be the center of attention. Essentially, and this is true for all basics, extra flourishes severely limit your options for transforming a piece. Additionally, when choosing a basic like a shirtdress, always keep these three things in mind (especially if you’re on a limited budget!):

1. Quality: Don’t buy basics in bad (read: unbreathable or impossibly delicate) fabrics and make sure seams and buttons are well-sewn. Be sure the garment is easy to care for; otherwise, your newly beloved will be on its way to the trash can faster than designer ripoffs hit the floor.

2. Fit: Every basic you buy should fit like it was made for you; not uncomfortable, not too tight, not too fussy. There are so many options out there, so you shouldn’t buy anything that doesn’t make you feel like a bombshell when you slip it on. Fit is the secret to every successful look. Don't go blindly into buying—the fit is your friend and so is the mirror, if not the salesperson…

3. Application: If you’ve followed the tips above, you’ve already sunk time into your purchase, so make sure it’s worth it! A new basic should be able to work with multiple pieces already in your closet.