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.

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.

A new outfit from Kimberly Smith of Penny Pincher Fashion, whom we introduced to YLF in October 2013.

Kimberly is sporting black faux leather skinny pants with a toffee crew neck sweater. Semi-tucking the sweater lengthens the leg line, so does pairing the pants with high-heeled booties. The suede booties add extra textural interest and echo the sweater colour. Our blogger’s chain-strap crossbody in toffee and black complements her outfit beautifully. Kimberly then adds a bouclé coat in a tailored Modern Classic cut. The rich jewel-toned teal is unexpected and fab with the warm-toned toffee of her sweater and footwear. A chevron scarf with subtle toffee accent, on-trend rib-knit hat with faux-fur pom-pom, and a simple gold pendant finish off the look to perfection.

Solid grey is my least favourite neutral, and overly cool for my warm complexion. In Seattle, where the days are grey for half the year, it’s the last colour I want to wear close to my face. I will wear grey in a pattern, or sport light pearl grey footwear and bag, but that’s it. 

I do like grey on those who wear it well. Shades of grey tend to look fabulous on cool-toned complexions. Most of all, grey is SPECTACULAR with grey, silver, white, or salt & pepper hair. It picks up the colours running through their hair. Colour repetition is complementary, flattering, and pulls an outfit together, which is why it’s pleasing to the eye. Clients with grey or greying hair look sublime wearing grey. Husband Greg has a salt & pepper ‘do and wears shades of grey with the best of them.

Just look at how well the grey-haired model I have used in these examples wears grey.

1. Ombréd Cool Tones

Both the light and dark grey in the pattern are repeated in the model’s hair. The cool-toned blue hem and black bottoms work well with her cool-toned complexion.

2. Greyed Green

This shade of seafoam is so unsaturated that it can almost pass for grey, and therefore picks up the grey in the model’s hair. Silvery grey footwear does a good job of bookending, and the silvery jewellery is the grey cherry on top. Tonal, elegant, and beautiful. My favourite of the four outfits.

3. Black & Grey

The grey dots in the black pattern pick up the grey in the model’s hair. The shades of grey in the necklace and silver earrings do the same. I’d have preferred the outfit with silver footwear, but the black elongates the line of the leggings and looks great too.

4. Warm Greys

The textured greys in the poncho have a taupe tinge to them that warms the palette. Although taupe is a cool neutral, it’s relatively warmer than grey and therefore brings out the warmer grey hues in the model’s hair. The warm gold earrings are an unexpected addition. The column of black cools the palette back down.

When my hair goes grey, I bet I will enjoy wearing solid greys a whole lot more. In the meantime, over to you. Do you wear grey, and do you have greying hair to complement grey wardrobe items?

Holiday parties are a lot more relaxed than they used to be, which brings me to the casual holiday dress. It is comfortable, sleeved and insulating. No form-fitting silhouettes that need shapewear. No need to find the right topper because it’s sleeveless. No worries that your outfit looks best with a jacket, because the dress does all the talking. And you can wear comfortable and practical footwear.

A shout-out to Artful Home where they sell eclectic and arty holiday attire from an XS to XXL (size US2/4 to US18/20). Silhouettes are fluid, a little architectural, and provide ample coverage. I found this site through the wonderful Brenda Kinsel, who wears their items with panache.

Here are some neutral and understated renditions to get you started, but feel free to add more colour and pattern. You might also like the combinations for settings other than casual holiday parties.

1. Arty Tartan

A sleeved A-line dress in a pattern made of substantial fabric WITH pockets and a versatile neckline ticks off all the boxes. It’s warm, comfortable, interesting, festive, forgiving and elegant. Throw it on over leggings or hosiery with a pair of flat or heeled shoes, and Bob’s your uncle. Add bling, a clutch, lippie, and possibly fingernail polish. Brenda Kinsel wears this dress with grace and panache. I love her dressier additions of fishnet hosiery, matching specs, low-heeled ankle strap pumps, and sparkly expressions. You can also keep the look more casual with leggings, skinnies, flats or casual boots.

2. Magical Movement

This type of drapey dress works on most body types. It’s just structured enough through the sleeves and upper torso, and lets the volume and colour-blocking below the bust create movement and interest. Wear it over leggings, skinnies or hosiery, and add anything from ballet flats, booties, and shooties, to oxfords, Docs, pumps and ankle strap looks as footwear. Add festive bling to dress up or dress down this look as much as you like.

3. Cosy Cardi Layers

An A-line shift dress in a jersey or silky fabric looks surprisingly good with a tailored maxi cardigan worn loose like a casual jacket. A fine gauge knit cardigan is dressier than a chunky knit, and can be longer than the dress. Finish off the look with hosiery, boots or pumps, flats or oxfords, and some bling.

4. Sweatered & Booted

A great sweater dress is a beautiful thing because it’s the warmest and most versatile option. The turtleneck midi here has been layered with a cardigan, but you can wear the dress on its own with hosiery and your choice of dressy or casual footwear. You can add a scarf instead of a necklace. Finish off the look with bling and bag that make you smile.

I wore formula #4 to a few casual events last year, but more frequently when I work with clients. It’s a workhorse olive sweater dress from Banana Republic that is my go-to Winter dress. It’s gorgeous quality and hasn’t pilled, stretched out of shape, or shrunk. I wish I had it in other colours. I dress it up with hosiery or boots, shooties, pumps or heeled oxfords, and pick from my large capsule of handbags and outerwear to change up the palette and the mood. I’m happy to pattern mix up to three patterns in an outfit. I’ve also dressed it down with cream hi-top Converse sneakers and a guitar-strap crossbody bag. I often wear it with a scarf for warmth, which I either drape around my neck indoors or take off. Here are the exact items from my wardrobe that I mix and match to create an assortment of outfits.