How to Dress Outside Your Comfort Zone

Meet Jill Lansky!

The style + beauty blogger behind The August Diaries, a visual diary with style tips, beauty tutorials, travel guides, + life experiences. As a digital and style influencer, she empowers her readers to become the best version of themselves and to use clothing as a means to gain confidence.

She is also a YouTuber + produces easy makeup tutorials that real women can learn from. Follow along on her blog + Instagram for more inspiration and to connect with her!

How to Dress Outside Your Comfort Zone

It’s probably fairly obvious that I rarely dress outside my comfort zone (although I’m making more of an effort to!). I have staples – denim, moto boots, leather jackets and messy waves – that I feel good in, so that’s what I always resort to. And I feel confident in my personal style, but sometimes I crave pushing myself when it comes to fashion. Especially during Fashion Month and when runway looks are circulating, I get inspired to try something fresh.

If you’re wanting to push your own boundaries, my biggest suggestion is not overspending on an item. Here are 3 places to start:


Before this year, I was all about dainty gold jewellery – nothing else. But after seeing chunky gold earrings everywhere, I bought a couple pairs and haven’t taken them off.


Makeup is another place I’ve been switching things up, namely with this blush-colored tutorial. I don’t think I own a single piece of pink anything, but I’m in love with this current beauty trend. I’m also adding more colour into my wardrobe, starting with my makeup – this red lip has become a fav!


Without spending a ton, you can absolutely play around with shoes. I’ve found some of my favorite pairs at places like Forever 21 and H&M. If you end up trying something new and hating them, you won’t completely break the bank.

Aritzia blouse | Levi’s denim shorts | Givenchy slides (save version here) | Proenza Schouler Hava bag | Cuchara Kitson necklace | Lisbeth necklace


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