Dresses are generally hard to fit, and sweater dresses can be the hardest of all. Too short, tight, itchy, lightweight, shapeless, or just all-round unflattering. That said, when you find a sweater dress that works, it’s the best Winter dress because it’s warm, cosy and versatile. Dress it up or down, layer it with hosiery and toppers, and combine it with any style of boots. 

Sweater dresses come in many variations. Short, long, body-con, fluid, A-line, solid, patterned, casual, dressy, sporty, retro, chunky, fine gauge, and belted. Take your pick.

Hobbs
Greta Dress
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Boden
Cynthia Dress
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Boden
Cynthia Dress
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In 2008 I wrote a post on how to find a flattering sweater dress and the guidelines are just as relevant ten years later. I’ve changed my preference for my perfect length though. A decade ago, I liked my sweater dresses just above the knee, and now I like them just below the knee.

I’ve had many sweater dresses over the years and loved them all. They became instant workhorses because you can throw them on with fun hosiery, boots, a topper, scarf, bag, and not feel cold in the dead of Winter. They are a fabulous change to jeans and pants. If only it weren’t so hard to find a perfect fit. I currently have one midi sweater dress from last season and I am constantly on the lookout for more. My challenges are insufficient length, a fit that’s too body-con, a neckline that’s too wide, bad quality, or flimsy fabric. Or I find a fabulous fit and great quality but it’s in a colour I don’t like, or at a price I don’t want to pay.

These sweater dress guidelines aren’t flop proof, but they might help get you on your way.

1. Embrace a Fluid or Oversized Fit

Surrender the waist with a very straight cut, or avant-garde and arty silhouette that drapes over lumps, bumps and extra bits in an architectural way if body-con fits are not your thing. This type of gently fluid or very voluminous cut can work on any body type when there is just enough structure in the outfit. My olive sweater turtleneck sweater dress is fluid and straight through the body, hugs my hips and bottom a little, and tapers at the hem for structure.

2. Consider an Empire Cut

The baby doll style is an extra roomy option on the bottom, making it a forgiving A-line silhouette. Good for apple shapes, pear shapes, and even straighter figures who crave ample movement. A larger bust needs a lower neckline in this style, and the empire cut should not cut across the bust.

3. Find a Fit & Flare

If you’re curvy or very curvy and prefer to define the waist, silhouettes that are belted or fitted on the torso create that type of structure. The flared bottom creates movement and camouflages hip and thigh extra bits you don’t feel comfortable showcasing. You can also add a wide belt to a fluid fit dress to define the waist.

4. Choose Heavier Knits

This does not necessarily mean “chunky knit” because fine gauge knits can be substantial (like the knit of my olive sweater dress). Knits with weight smooth over the contour of the body instead of grabbing onto curves in an unflattering way. Chunky knit sweater dresses with a fluid fit can also be a lot more flattering than you think.

5. Get the Length Right

Sweater dresses can’t be hemmed, which means that the length has to be perfect upon purchase. I like them just below the knees these days, or a little longer. But many of my clients prefer them on the knee, or just above the knee if the fits are voluminous and the knit is chunky. Some will wear them a whole lot shorter with very tall boots and opaques.

6. Complete the Outfit

Make sure you try a potential sweater dress with the right support act before you say no thank you. The right shoes and hosiery can make the difference. And remember that shapewear is a lot more comfortable than it used to be.

7. Block the Dress Back to Size

Sweater dresses can lose their perfect shape and fit after laundering. This is usually an easy fix with the steam iron that presses out wrinkles, and blocks the areas back to the right shape.

And last, you can wear a knee-length sweater dress over cropped flares, cropped straights, culottes, bootcuts, leggings and skinnies if you like. I LOVE this outfit, although I’d wear flat white booties and a white bag. For this look, I would get a knee-length sweater dress instead of a knee-covering one.

DURO OLOWU Polka-dot Jacquard Wool Sweater Dress