These outfits caught my eye because we haven’t seen flowing dresses paired with jeans, leggings and trousers for a while. Wearing fitted dresses over jeans, both tapered and bootcut, was a fashionable look about eight years ago, and it’s fun to see the look rekindled and updated. This time the frock is more flowing with the option of an added tunic sweater. 

In the pictures above the models are wearing the same silk crepe V-neck tunic dress in different colours. A white dress over grey jeans, and a black dress over leggings. The high-low hemline is extra long at the back, creating an avant-garde integrity. The shorter front gives the outfit structure, as does its lack of sleeves (remember that exposed skin adds structure to an outfit.) Slim-fit pants add further structure. The heel elongates the line of the look.

In this variation, a low contrast lightweight and texture-rich V-neck tunic sweater has been layered over the dress, jeans and heels combination. The asymmetrical hemline creates diagonal lines both in front and at the back, which adds structure. There is something magical about diagonal lines that draws the eye up, which accentuates an elongated silhouette. The effect of the layered look would have been completely different if the dress and sweater were straight-hemmed, high-contrasting pieces. In that case, you’d have added extra horizontal lines to the outfit, which wouldn’t have been as conventionally flattering. 

The tailored bodice and sleeves of the sweater add further structure to the layered look. Voluminous sleeves would work in a shorter length, with the exposed skin adding structure.

Do NOT think that this outfit combination will only work on supermodel body types. Not at all. As a regular height lass you’ll be fine wearing these layers with a heel. Taller lasses may not need the heel. I have a 6ft, size 12/14 client who wears this look beautifully with flat sandals, loafers and ballet slippers. 

As a petite, you can make the look work by shortening the length of the dress and sweater a little to even out proportions. Create enough outfit structure so that those long loose layers don’t boss you around. Choose a V-neckline for outfit elongation. Keep the colour contrast between the layers low to prevent extra horizontal lines. And wear low or high heels. 

This is a refreshingly elegant and arty look, with romantic layers that are as angular as they are soft and pretty. Comfortable, forgiving on the midriff, and interesting. Who’s in?

I call shoes “flats” when the heels are no higher than one inch. So flats actually come in an assortment of heel heights (as shown below). Even the flattest heels are around a quarter of an inch high.

It is hard to make an exact cutoff point, but normally when a heel reaches 1.5 inches I call the shoes low heels, and not flats. Flatforms, which are essentially platformed heels sans the arch, are also heels and not flats.

I’d like to hear your thoughts. Where do you draw the line?

We devote a category to body type on YLF because the information provides a helpful starting point when you’re unsure about how to create conventionally flattering and balanced proportions for your shape. The suggestions there are useful and tangible, but they should be viewed as helpful guidelines and NOT as rules. Partly because no set of guidelines can completely cover the infinite variability of body shape, but also because conventional figure flattery is not the only way to be stylish. The edgiest and most fashion forward outfits are often not conventionally flattering at all. They are creative, trendsetting and “just flattering enough”.  

Over the years I’ve placed less and less emphasis on the importance of body type dressing guidelines. When YLF first got started almost 8 years ago, body types were all the rage. These days the idea of sticking to a prescribed way of dressing for one’s shape seems like a dated concept. We want to celebrate our freedom to wear what tickles our fancy. That’s why I thoroughly support looking beyond body type dressing rules in order to create interesting and individualistic looks, and most of all, to have fun on our style journey.

Bending the guidelines is not about wearing unflattering outfits that make you feel self-conscious and unattractive, just for the sake of looking unique and showcasing your creativity. Rather, it is about bending a guideline in just the right way so that you can create conventionally flattering proportions. By doing so you will have a larger variety of silhouettes and outfit combinations at your disposal than the strict guidelines would suggest.

Regardless of whether you are following, bending or throwing away the guidelines, I believe it helps to understand them. So over the next five weeks it will be back to first principles as I update the dressing guidelines across all five body types and in the context of current fashion trends.

Note that although the guidelines are general, most of us don’t look exactly like one of the prototypical shapes. So it will be up to you to filter through the information and use the parts that make sense for your shape. You will also need to take into account your figure flattery priorities. Sometimes you’ll adhere to the guidelines and wear conventionally flattering outfits. Other times you will let those creative juices flow and wear things that you love even though they sacrifice some degree of conventional figure flattery. Either way, there is only one rule to always keep in mind: Have fun with fashion.

YLF forum members have had excellent experiences with these two pairs of jeans. 

• Jennifer Lopez Bootcut Jeans: They are available in regular, plus and petite fits, and across a variety of short and longer lengths. Read the rave reviews. 
• Levi’s 525 Straight Legs: These are slimmer on the calf, but not “calf-sucking”. Also available in petites and across short and longer lengths. Read more rave reviews. 

One of our forum members was struggling to find jeans, even at high price points. She was thrilled when the Jennifer Lopez bootcuts fit the bill, and were also more affordable. Leave no retail stone unturned.