Lisa Fine of Quiet Town

Every morning, I see Lisa Fine, co-founder of Quiet Town, at elementary school drop-off. (Her kids go to the same school as Toby.) She always looks comfortable and cool, so it’s no surprise that “Anjelica Huston in the 1970s” is her style inspiration. With her laid-back vibe and talent for turning menswear into wardrobe staples, she’s nailing it. Here, Lisa shares five outfits she wore in a week…

Lisa Fine from Quiet Town

Sweater: Jesse Kamm, similar. Pants: Jesse Kamm. Shirt: J. Crew men’s, similar. High-tops: Converse.

“When I was pregnant, I wore stuff from the J. Crew men’s sale rack. It’s the best place to find a classic, oversized look. This striped shirt is a men’s extra large and after having babies I cut the bottom and sleeves off. Now I use it for layering all the time. Most mornings I get ready in five minutes because I’m taking my kids to school, so there are little mantras I use when getting dressed. One of them is ‘go monochromatic.’ If I put on a camel sweater and pants, to me it looks a little more elevated and planned because it’s monochromatic.”

Lisa Fine from Quiet Town


Sweater: Uniqlo men’s. Skirt: from India, similar. Trench: Unis, similar. High-tops: Converse.

“My husband and I went to India for our honeymoon, and I found this skirt in a vintage store. I loved the mirrors around the waist. I didn’t wear it for 10 years, but now I’m like, what took me so long? The message is definitely ‘don’t discredit the crazy things in your closet.’ The mirrors aren’t an everyday look, but with a big sweater over it, it works! Layering solves everything. My favorite layering pieces are black turtlenecks, chambray shirts, denim jackets, white fishermen’s sweaters and trench coats.”

Lisa Fine of Quiet Town

Sweater: J. Crew men’s. Slip: La Petite Coquette, similar. Hat: Rag & Bone. Clogs: From Tokyo, similar.

“I’m always shopping different parts of my dresser. Why not sleepwear? I have a belly pooch from my babies, but if you throw on a schlumpy oversized men’s sweater, then you’re accentuating this pretty nightgown without being too revealing. Funnily enough, I actually feel sexiest in oversized clothes — nothing makes me feel sexier than when something’s falling off a little! But it’s important not to be completely swallowed. Showing just a hint of an ankle or wrist is great.”

Lisa Fine of Quiet Town

Dress: Vintage, similar. Shirt: Madewell. High-tops: Converse.

“This dress is crazy so I try to temper it with a chambray shirt underneath. Narnia, where I got it, is the best vintage store in the world. This dress was $25. I realized if I played it down by adding a chambray shirt and high-tops, it would reflect real life. That helps it feel more down-to-earth, versus kooky. I wear it with Adidas shower slides in the summer. I try to keep the whole thing really chill. It has its own energy.”

Lisa Fine from Quiet Town

Jacket: Madewell, similar. Sweatshirt: Vintage, similar. Overalls: J. Crew, similar. Shoes: Vans, similar.

“My husband was at a bachelor party in D.C. They ended up in a vintage store and he got me this pink sweatshirt. I was like, ‘That’s so weird but cute that you’re shopping for me at a bachelor party!’ I love bright colors, especially when they’re toned down with a neutral like these khaki overalls, which are about 10 years old. I cut the bottom off them to create a raw hem. Oversized sweaters, high-waisted jeans and high-top sneakers are all part of my uniform. I’m a total disappointment to my daughter Sunny because I don’t have high heels in my closet.”

Thank you so much, Lisa! Your style is awesome.

P.S. Cool earrings and four more women share a week of outfits.

(Photos by Ana Schechter for Cup of Jo.)