Winter Investments

Fashion has always been a form of self-expression. Discover the winter styling essentials, layering techniques and investment pieces I return to season after season.

By Annie Nguyen, Fashion Designer

June 3, 2026

My first love for styling and experimenting with fashion started when I began collecting Bratz dolls. Through dressing and styling my dolls, I naturally started experimenting with my own style from a young age. Fashion became a way for me to play, create and express myself and that mindset has stayed with me ever since. No matter the weather or season, styling should always feel fun.

  • Philly Stripe Long Sleeve Knit Jumper - Ivory/Black
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Philly

Stripe Long Sleeve Knit Jumper - Ivory/Black

$139
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  • Greer Knee Length Skirt - Black

Greer

Knee Length Skirt - Black

$79

If you ever struggle with what to wear in winter because you want to stay warm without sacrificing style, the key is mastering the art of layering. You never want to leave the house feeling like your outfit is unfinished and the best way to elevate a winter look is through accessories and styling tricks that make an outfit feel more intentional and interesting. One of my favourite apps to use right now is Whering, which allows you to upload photos of your clothing and curate outfits using pieces already in your wardrobe. I love it because it gives you fresh ideas and helps you style items you already own in new ways.

  • Paige Faux Leather Cropped Jacket - Cherry Brown

Paige

Faux Leather Cropped Jacket - Cherry Brown

$239
  • Bailey Wrap Skirt Mini Dress - Charcoal Marle

Bailey

Wrap Skirt Mini Dress - Charcoal Marle

$159
  • Keaton Modal Long Sleeve Overlay Top - Espresso

Keaton

Modal Long Sleeve Overlay Top - Espresso

$89
  • Keaton Modal Straight Leg Overlay Pant - Espresso

Keaton

Modal Straight Leg Overlay Pant - Espresso

$109

Winter dressing is all about investing in timeless outerwear pieces that do the talking. My personal favourites are funnel neck jackets and the classic trench coat. Both instantly elevate an outfit while adding warmth, structure and versatility.

You also don’t need to pack away your favourite mini skirts and dresses once the temperature drops. Styling minis through winter is easier than you think. Simply pair them with stockings or crew length socks to create a chic, layered look. Shoes can completely make or break a winter outfit, so investing in versatile styles is essential. Knee high boots, mid length boots and chunky boots are staples in any winter wardrobe. Personally, I love styling cowboy boots to add texture and an effortless off duty feel to a look. For a more preppy combination, I like pairing loafers or ballet flats with oversized jumpers and shirts to create balance and keep the outfit from feeling overly polished.

  • Alden Short Trench Jacket - Black
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Alden

Short Trench Jacket - Black

$259
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  • Tanya Buttoned Long Sleeve Maxi Dress - White
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Tanya

Buttoned Long Sleeve Maxi Dress - White

$159
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I follow countless OOTD Instagram accounts from around the world for styling inspiration, but my favourite cities to watch are New York, Paris and Copenhagen. Their effortless approach to layering and winter styling constantly inspires me and gives me fresh ideas for dressing during the colder months. Creating a mood board of winter outfits is also a great way to plan your wardrobe ahead of the season. It helps you identify gaps in your wardrobe, build your wishlist and define the style direction you’re drawn to.

  • Laurelle Sleeveless Modal Draped Bodysuit - Chocolate

Laurelle

Sleeveless Modal Draped Bodysuit - Chocolate

$119
  • Bobby Oversized Jean With Front Pleat - Black

Bobby

Oversized Jean With Front Pleat - Black

$149
  • Curtis Faux Leather Bomber Jacket - Dark Chocolate

Curtis

Faux Leather Bomber Jacket - Dark Chocolate

$219
  • Coraline Long Sleeve Sheer Top - Neutral

Coraline

Long Sleeve Sheer Top - Neutral

$89

At the end of the day, there’s a difference between styling an outfit and simply wearing one and that difference is what truly makes or breaks a look. Create that moodboard, invest in accessories and timeless outerwear to really elevate your winter style.

Discover more from our Winter Edit.