Winter Dresses from Luxe to Less: The Shirt Dress

Welcome to the latest instalment of Luxe to Less, a popular post around these parts where I curate a range of different price points/options for a particular wardrobe staple.

Last week I kicked off a four week series on Winter dresses. It began with printed dresses and this week, it’s all about the shirt dress. I’ll cover knit and party/work dresses next.

Shirt dresses are fast becoming a modern fashion favourite, popping up across all seasons. Sleeveless and short sleeved versions were certainly trending in Spring and I for one am pleased to see this versatile style being carried over to Autumn/Winter.

Shirt dresses from luxe to less slider

1. Long Sleeve Shirt Dress in Olive, $69 from Target; 2. Elizabeth Dipped Hem Shirt Dress, $99.95 from Forever New; 3. Adventure Check Shirt Dress, $99.95 from Sportsgirl; 4. Tie Shirt Waist Dress, $109.95 from Sportsgirl; 5. Drop Pocket Shirt Dress, $129.95 from Witchery; 6. Long Sleeve Shirt Dress,^ was $129.95, now on sale for $79.95, from French Connection; 7. Charlie Pleated Yoke Dress,^ $149 from Bohemian Traders; 8. Dark Denim Shirt Dress, $149.95 from Witchery.

As you can see from the selection above, there are a few stand out trends in shirt dresses at the moment:

– a longer, dressier, unbelted shift style, like (5) and (6), which works well for work and dressy do’s;

– the more traditional belted style (1, 2 and 4) which is a versatile smart casual option; and

– the more casual, straight version in plaid (3 and 6) and denim (8).

I love a shirt dress (I’ve waxed lyrical about them previously here) as the button detailing creates some interest and gives you some choice about your neckline – whether buttoned right up or showing some decolletage.

A shirt dress is also a great option for anyone breastfeeding too.

So how to style your shirt dress this Winter?

1. Tights and boots are always a good idea – any of these shirt dresses would look great with a pair of opaque tights and boots, as I’m wearing below.


Wearing Flannel Shirt Dress by Country Road, Seed Heritage ankle books from last Winter and Ambra tights. Earrings by Ralph Lauren and bangles from Mimco and Silverberry, Bali.

Above, I’m wearing the Flannel Shirt Dress by Country Road, which is now back in stock in most sizes. It’s a generous cut as I’m wearing a size 10 and it’s still roomy. It’s made from a good mid weight fabric too which is perfect for milder Winter days here in Melbourne.

2. Take off the belt – even if you generally gravitate to belted or waisted styles (as I do as they suit me), don’t be afraid to take off the belt to create a different, perhaps more casual, straight fit too. Throw on a pair of trainers and you’ve got yourself a very comfortable every day outfit.


Sans belt … ta da!

3. Pump it Up – Dressier styles also work well with a heeled pump for work and are perfect for a Friday work to work drinks scenario.

4. Layer Up – In cold weather, don’t be afraid to layer up your shirt dress with a long sleeved tee or a fine knit turtleneck underneath or a faux fur vest or chunky cardigan on top for extra warmth.

5. Change it Up – replace the fabric belt with a leather one to create a different look.

For more shirt dress options, check out this fab post on Winter dresses by Beach Style Mum here. For inspiration and ideas for styling a chambray shirt dress, join in the Style It Project with Kimba Likes.

^ denotes an affiliate link – you don’t pay anymore but I earn a small commission.

Are you a fan of the shirt dress? Which frock is your pick? Is there a shirt dress in your wardrobe?