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When you feel safest while dressed in form-fitting clothes and high-heels, it can be hard to branch out towards less feminine styles that might be perceived as less sexy or attention-grabbing. Nevertheless, more minimalist fashion trends have a certain allure when they are so darn comfortable and cozy– especially during the colder, winter months when long cardigans, over-sized winter coats, and flat booties will rule supreme in your wardrobe. During this Thanksgiving long weekend, I tried my own version of ‘hobo chic’ with this particular combination.

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Since I tend to buy brighter colours and vivid patterns, it was hard to maintain a theme of muted colours. This time, however, I wore a blush pink midi skirt from Topshop (which features an interesting texture, asymmetrical hem-line, and side slit), a lace top, and a cozy long cardigan from The Gap (which I just bought at a 40% discount). As the crowning detail, I added a bit more femininity into this outfit with a new toque recently acquired from Aldo– I adore how the bejeweled details adds instant glamour to an otherwise plain accessory. Lastly, I wore these incredibly comfortable Jeffrey Campbell booties to complete my laid-back yet subtly stylish outfit.

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 Cardigan // The Gap

Top // Hong Kong Boutique

Toque // Aldo

Shoes // Jeffrey Campbell

Skirt // Topshop

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Images Credit: What Doffy Does

Would you try your own brand of hobo chic? Don’t be afraid to take trends that are outside of your comfort zone and transform them into your personal brand with little details here and there. Within reasonable limits, I feel that most people are unnecessarily afraid of wearing new styles and fashions– as long as you style it right, you probably can wear almost anything!