How to Wear… Winter Woolies

Today in Cape Town is a definite reminder that Winter is on it’s way! This means a whole new way of dressing in the coming months… woolies, boots, layers, beanies all come into their own during this season.

Winter is a far easier season to hide certain “bits” which means I do prefer dressing in winter, but I still have a tough time knowing how to look fashionable while doing this. When I wear winter knits I end up looking like a bundled up bag lady!

This is where I thought it would be useful to get some tips for how to wear winter woolies while still looking trendy! Enter Candice, a personal stylist and shopper with her own business, With-Style, who is here to share with us some tips on how to do this….

I have just arrived back in Cape Town from a holiday in sunny Clarens only to discover that winter sneaked back in again! I really wasn’t ready for the mental shift from summer paradise to this grey, wet weather feel. However, chin up! It is time to trade in our summer dresses for heavier fabrics. What better way to warm up than to snuggle into our winter knitwear. Fashion is often a little stingy on good old comfortable knitwear but this year the fashion brigade are loving the knitted jumpers and we can have so much fun putting new looks together!

Let me rattle off some of the trends just so you know what’s what, and then we can look at my suggestions on the knits that really work. You can hit winter with chunky knits, star prints, bug and animal motifs, neons, oversize jerseys, capes, knits with leather inserts or bling, and also metallic knitwear! Knitted jumpers are trending and have even made the red carpet thanks to the super stylish Olivia Palermo.


With the reintroduction of oversized clothing the trending jerseys have an 80’s edge. Fortunately the ‘glammed’ up jersey is a look that is easy to work with. Slip into your skinny jeans, add a gorgeous loose fit sweater, a bag with metal detail, and sexy heels. Very easy, very sexy! If, like me, you are not inclined to heels during the day, then pumps, loafers or short flat boots are perfectly suitable. This is a good chance to show some leather pocket detail or to bring some bling into your look. The chunky necklaces are still very strong so its quite economical to have one or two in your wardrobe and then mix them in with different jerseys.


You are not limited to skinny pants alone. A major trend that is a keeper for any wardrobe is the leather skirt. Tight pencil style or an A-line cut, it will work beautifully next to the soft texture of a knitted top. Another one of my favorite trends was reworked this year and it was really lovely in the Paul & Jo collection. The loose relaxed jumper with beautifully cut but loose trousers, not skinnies, which can have such an ‘I am just effortlessly stylish’ confidence to it. Fabric and cut really are the key points here.

Seen often on style guru Alexa Chung is the jersey with the little collar of the blouse pulled through. This preppy look is fairly timeless and you can work it with skinnies, skirts and pleat front trousers. Animal motifs can give it some zing too such as the cute owl motif sported by Kate Bosworth!


So ladies I hope this is useful. Right now I am heading to my wardrobe, its time to unpack and revive my winter gear. Warm and cozy knits, here I come!

Author: Candice Ilic, With-Style

Kathryn Rossiter

Kathryn is a South African lifestyle blogger and mom of 2 who has been blogging daily for over 9 years! She writes about travel, health, beauty, fashion, decor and family... but not food (unless it's food she's eaten made by someone else) as she is a hopeless cook. She only wakes up early for 2 things... a red-eye flight to somewhere exotic and early morning game drives. She has just finished an extensive home renovation and would prefer to never see another box again. She's never met a chocolate or glass of bubbles that she didn't like!

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