Do you ever watch IFC (The Independent Film Channel)?  Lately, they have been showing some old movies from the 80’s and 90’s, like The Breakfast Club, Sixteen Candles, Weird Science, and more.  The funniest thing about watching these movies is realizing how normal it has become to see the edited versions on network television with the curse words omitted.

This past weekend IFC aired Uncle Buck.  Remember that movie with John Candy and a young Macaulay Culkin?  I admit, for some strange reason I watch that movie every time it is on.  One thing that grabs me about the movie is how perfectly they captured the teen style of the late 80’s and early 90’s through the character Tia, played by Jean Louisa Kelly.

Shift Dresses

Seriously, if you want to really get a sense of what is going on with trends today, do a weekend movie binge of your favorite films from the late 80’s and early 90’s.  It’s all there.   I bet if I didn’t tell you that the image above was from the movie Uncle Buck, you would probably assume it was more recent.  Yes, what goes around eventually comes around.

One trend from this era that is back, and has me a bit conflicted, is the casual shift dress.  Be them in knits, like sweaters and sweatshirts, or wovens, you have probably seen these shapeless little dresses everywhere.  When I first spotted them, the part of myself that has absolutely no self-control, a strong desire for comfort and not sucking it in, breathed a sigh of relief. Super soft fabrics and no waist constriction?  Sign Me UP!   I started imagining how carefree I could be this winter.  How many times I could say “yes, please” to second helpings, along with all the body mysteries I would be able to cover up.

Yet, the other side of me imagined myself, my very curvy, big busted, wide-thighed, self in these dresses and got a little freaked.  Do I really want to look like a heap of laundry with a head?  Sure I may be comfortable, but at what cost?  Sometimes I just wish the world was blind.

So, yes, whie I’m conflicted, I really want to see if I can pull off a dress like this because they look so cozy.  With so many of them out there, there is bound to be one that will fit my body.  Thankfully, because I am a stylist, I will know how to be discerning when choosing the right one.  But if you considering a dress like this and don’t know what to look for, Here is my advice below, along with my tips on how to style, easy shift dresses for fall.  They’re quite versatile!

How to Wear Easy Shift Dresses This Fall

Using this drop-waist shift from Boden, here are some ideas for how you can stylishly, and figure-flatteringly, wear this comfortable dress  this fall and winter.

Before I get into some styling tips, let’s first touch on body shapes and what the right styles are for each body type.  Fair or not, these dresses are made for bean poles.  If you don’t have much body fat, or are boyishly straight, well good for you, and enjoy the limitless abundance of options out there.   This is not to say that we all can’t wear shift dresses, but if you have some meat on your bones, depending on where your meat is located, there are a few things to keep in mind.

If you are bottom heavy- Choose dresses without a lot of flounce at the hem and avoid ones that have dropped waist seams that cut horizontally across the wides part of your hips.  All these features will do is drag the eye down and make your butt and hips look bigger.  Instead, look for straighter styles or wedge shapes that taper slightly at the hem.  You can also look for styles that skim more closely to the body or have some subtle waist shape.

If you are busty- If you are very busty be very careful of these styles.  Busty women have defined waists and by bypassing the waist with dresses like this you risk looking as wide as your boobs.  Instead of boxy, look for clean silhouettes that graze the ribcage area and then flare slightly.  What this does is show off that you do have a waist and are not as heavy as your boobs seem to indicate.

If you have a tummy- Dresses like these seem to be gifts from God for women with tummies.  However, even those with muffin tops need to be careful in very shapeless dresses.  Shapeless dresses may seem like they cover a multitude of sins, but they can also show off every lump and bump and can make a woman look bigger than she is.  If you have a slight tummy, choose dresses in fabrics that are a bit heftier vs. flimsy fabrics that don’t contain the lumps and bumps.

Take a look at how I styled this one dress below to give you ideas on how to wear it.  Also included will be some more body dressing tips.  At the end of the post, be sure to check out some other styles out there to consider.

Outfit #1

Approach these dresses almost like oversized sweaters.  Yes, they are technically dresses, and you can certainly them this way, but the approach to styling them can also be more like how you think about styling your relaxed tops.  Here, for example, I layered this dress over a chambray buttondown from J. Crew.  With this look, I would probably add a dark pair of chocolate opaque tights that would look great with a pair of brown riding boots, like these from Modcloth.  For this easy weekend look, I added a Dooney & Bourke handbag, Michael Kors padlock earrings and corded bracelet from Max & Chloe.

Outfit #2

Another way to wear this dress is to just embrace the drape and add something equally drapey over it, like this relaxed sweater vest from Lord & Taylor.  There are a few trends going on by doing this.  First, the long over short trends (which was huge in the 90’s and back now), along with the large over lean trend.  If you want to embrace this, casual, somewhat boho trend, do it with this word of caution: Add some height to your outfit through your shoes, especially if you are short or very apple-shaped.  With so much bulk on top, you run the risk of now only looking short, but wide, in outfits like this.  By adding some height through heels, your overall appearance will be elongated, which will make you look slimmer and give you back some height that this outfit has taken away.  You don’t have to do spindly heels.  A chunky, stacked heel pair of boots, like these from Steve Madden, can add height and comfort.  To finish this outfit in a super casual way, I added this statement necklace and suede fringe handbag.  An outfit like this would look great with brown tights or heather grey ones.

Outfit #3

As I said earlier, you can treat these dresses like tunic sweaters or tops.  In fact, if you are very tall, using these dresses as tops could be your answer when wearing leggings.  That is exactly how I styled it here, using this pair from Athleta.  Dresses like this are great for casual days, especially styled accordingly, like with a denim jacket, easy scarf, these grey slip on sneakers, casual handbag, like this one from Le Sportsac, and some easy jewelry, like a long gold necklace and stud earrings.

Outfit #4

Dresses like this are not just for times that you are feeling like a garden slug.  The beauty of accessories is that you can take one piece from super casual to dressier.  Here, using the same dress, I jazzed up the look using this bib necklace from Bauble Bar, bracelet from Banana Republic and red lace up booties from Anthropologie.  When I saw those booties I stopped dead in my tracks.  God, I love them.  Not only would they work great with a shift dress but, man, would they look amazing with a sharp pair of tailored pants.  Anyway… back to this outfit.  Finishing the look I added a grey Vince Camuto handbag and pictured how great this outfit would look with grey or black tights.

Outfit #5

With such an open scoop neck, a slim turtleneck, like this one from the Gap, is another way to style this dress.  Keeping it monochromatic, I added a Frye crossbody bag and heather grey oxfords.  What I like about this outfit is you can add a splash of color with tights.  Imagine how cool a pair of tights in burgundy, teal, dark green, or even yellow, would look.  However, if you want more warmth, you can also just add a pair of leggings too.  To keep it playfully casual, I finished this outfit with a pair of star studs.

Shop for fall shift dresses

Now that I have finished these outfits, I really hope I find a figure flattering fall shift dress.  If you are on the search too, check out these additional styles.