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Outfit Styling

Styling & Outfit Inspiration for Jenny Overalls & Trousers

Thank you kindly for the enthusiastic response to our latest pattern, the Jenny Overalls & Trousers pattern!  I’m excited about this release since they are so many darn views, with hopefully a little something for everyone. Today I’ll be sharing some images for styling and outfit inspiration; there are a million ways to wear Jenny, and I’m hoping this post will help you figure out how.


Most overall designs skew more functional than aesthetic, but I think the high waist and wide legs of Jenny feels a little more glammed up than your typical workman’s Dickies. I really encourage you to think about fabric. For a structured (and durable) look, choose medium to heavy weight denim. A lighter weight, drapier fabric like linen is also an option, and makes the leg feel softer and floatier. The cropped length feels the most modern, but I love the drama and formality of the full length leg, especially with a heel; it makes your legs look about a million miles long.

I favour this high waisted style with a shirt that can be tucked in; an oxford button down or closer fitting tee are ideal, but I also like wearing my Jenny overalls with a longer, drapey tee with a bit of volume.


Shorty overalls tend to feel more youthful to me (I am a  teenager of the 90s, after all) but I think they can feel more sophisticated with the right fabric; velvet, suede or even just basic black grow them up a little bit. In denim with a striped shirt, they are an outfit you can take straight through to September.


Cropped wide-leg pants are having a serious moment, and I don’t think it will end anytime soon. After so many years of skinny jeans and slim fitting pants, the silhouette feels fresh and modern even a couple of years into the trend, and pairing these pants with a cropped shirt is hands down my favourite look right now (I wear some variation on this look almost every day). The full-length trousers are more formal and put together; paired with heels they are supremely elegant for evening and make those legs go on forever. Hemmed to wear with flats, they can add a little polish to a more casual outfit.


I love high waisted shorts but I find they tend to ride up; I think the more generous crotch of Jenny makes these a super comfortable summer option. When it’s hot you need room to breathe. Since the shorts are tailored and chic, I think some of you could pull them off for work, or dress them up with a simple pair of heels. I know I’ll be wearing mine with flat leather sandals and silk camisoles all summer long.

Later this week I’ll be back with a fitting post. How are you planning to style Jenny?