• Connecting you to Australia’s best dress rental boutiques
  • Browse over 7,000 dresses and accessories for hire
Fashion Tips

7 Ways To Dress Tomboy Chic This Winter

Winter has officially arrived, bringing booties, oversize jumpers and coats to the forefront. The cooler seasons bring more flexibility to the wardrobe as you can layer, mix and match and get away with a casual androgynous look, personalised to your own tastes. Tomboy chic sums up the mix between this masculine and feminine aesthetic that balances items that are a bit baggy and a bit tight. Think Cara Delevigne, Ellen Page, the Olsen twins and Kristen Stewart all rolled into one. There are so many looks you can go for when it comes to tomboy chic, and the best part about sporting this look in winter is the versatility that comes with it.

We’ve put together a 7 step guide to help you achieve this cool and collected tomboy look that will make your winter a whole lot better.

1. Suit pants and office wear

These pants can go a long way and can be worn differently each time, whatever the occasion. Invest in a good pair and mix them with a tucked in or tucked out turtle neck, oversize tee or jumper, fitted shirt, blazer and a number of different shoes to suit all the seasons of the year. What’s more, you can wear them at work or style them with pumps and a leather crop jacket on the weekend.

Photo: Anthropologie

2. Layers, layers, layers

The best thing about dressing tomboy chic in winter is being able to match random pieces together, some that may have not been worn in a long time. Suit jackets with sweaters and denim or cotton shirts are always a good combination and can be styled with any type of pant including denim – straight-cut, boyfriend or skinny leg jeans are all good choices. Add a pair of worn converse or combat boots to top off your tomboy chic look.

Photo: Rooftop Antics

3. Mixing and matching

Dressing tomboy chic allows you to experiment with a mix of old and new pieces of clothing. If you’re in the mood to dress casual, but have a social occasion to attend, you can get away with combining a dressy pant with a sweater and shirt and accessories to suit your own personal style. If you have a collection of vintage style pieces, don’t be afraid to wear them with modern items to add to the overall edgy look, even if it is a pink dress with knee-high socks and a blazer over the top.

Photo: Jordan Zobrist – devonrachel.com
Photo: Collage Vintage

4. Tweed

If your grandma or even grandpa are having a closet clean out, double check whether they have any tweed coats they no longer want! Tweed is the ultimate addition to the tomboy chic aesthetic, adding a classic quality to the entire outfit. You can mix tweed with a pant or skirt, blending well with literally any colour. A favourite would have to be a camel or brown coloured tweed blazer that is reminiscent of the vintage British style – think equestrian mixed with Burberry. Check out this Thurley tweed number currently for hire.

Photo: Lena Modigh
Photo: Death By Elocution

5. Keep it simple

Tomboy chic may be a great way to mix the old with the new, but it can also be styled minimally through a simple monochromatic palette. Basic quality pieces are ideal for this and can be dressed up or down. Grey, black, navy and white are all versatile hues that can be mixed with each other or kept together to add to the minimalist, effortless yet ultramodern look. Designer sneakers are a nice way to keep the outfit super contemporary.



Photo: North Fashion
Photo: Give Me That Thing
Photo: Death By Elocution

6. Accessorize

Dressing tomboy chic doesn’t mean you can’t wear your favourite accessories, even a fedora or baseball cap in winter can be worn when styled well. Beaded bracelets or masculine watches are a good touch to any tomboy chic outfit. Samantha Wills is also known for her embellished pieces that are not only versatile, but full of personality and character. Gold, silver or fitted with rustic looking gemstones, you’ll be sure to find a statement bracelet or ring that will elevate your overall style.

Photo: My Scuttle
Photo: Matches Fashion
Photo: Natalie Dressed
Photo: Glam Radar
Photo: Mikutas Instagram
Photo: Mikutas Instagram

7. Snazz it up

So far we’ve shown you a variety of ways to rock the tomboy chic look, but what about if you want to dress it up a bit more with a snazzy touch? Tomboy chic isn’t just sneakers and brogues. Add a pair of heels or pumps for the ultimate tomboy chic formal flair and top it off with a fur coat for a dash or elegance. Unreal Fur do amazing fur coats ranging from pink, blue, emerald green, black or white.

Photo: Chloe Rose Boutique tumblr
Photo: Fashion Gone Rogue
Photo: Fashion Gone Rogue
Photo: Uh La La Land tumblr
Photo: Fashion Cognoscente
Photo: Maja Wyh – Who What Wear