Every girl knows that certain jeans need certain shoes. Bootcuts require boots, flares are better with heels… At Jean Stories, we’re typically inclined to let the denim dictate the shoes we wear. But what if we were to flip it, and do as designer Jessie Randall of Loeffler Randall does?…let fit follow footwear. What jeans would we (could we!) wear then?

There is no absolute answer to this question, of course, but that didn’t make me any less interested in the denim that Jessie reaches for when she’s in the mood for the more casual styles from her collection, such as the cross-strap Petra sandals (which she wears here), or the raffia Cora sneakers (see below). Her go-to? Striped overalls from Forever21. Not just because they look great with flats (her favorite), but also because they help her get her job done. “My ideal outfit is one where I am comfortable and still look chic enough to be in my office in Soho,” she told me when we photographed her in her totally stunning, totally soothing home in Park Slope, Brooklyn. “The comfort part helps me be more creative. I can’t think when I have some uptight outfit on.”

I love Loeffler Randall shoes, and after spending some quality time with Jessie, not just at her home but on a field trip to Savannah, GA recently, too, I love them even more. Reason enough for me to pick a pair of jeans because of how good they look with a shoe, for once? Yes, absolutely.

Use one word to describe your overalls:


What do you love most about them?

I like the ticking pattern. They go with everything, but also have a bit of interest because of the pattern.

Is there something about the fit of them that you feel works perfectly for your body type?

Yes, I love that there are adjustable straps. I have a bit of a long waist/torso so it’s nice to be able to make this adjustment.

…for your lifestyle?

I like the ease and vibe of rompers. Overalls are the denim version of a romper.

…for the shoes you make and personally love to wear?

These overalls look great with the more casual shoes in my wardrobe, from my cork sandals, to my raffia sneakers, to my double-height espadrille lace-ups.

Click on a pic to get closer…

If your overalls could give us a word of advice – maybe it’s something you’ve learned while wearing them – what would it be?

Just be yourself.

What do your overalls know about you that we don’t know?

How important comfort is in my daily look. I have no patience for anything that isn’t completely comfortable and easy to wear.

What’s the best thing you could be doing in your overalls right now?

Painting watercolors with my kids.

If you could go anywhere in the world in them tomorrow, where would it be?

When I travel, I only want to go to the beach. So, I would head to Jamaica and wear these on the plane.

What’s the best possible ending you could imagine for your overalls, if they had to go?

Maybe I could take the fabric and make them into a quilt or a rag doll for the little ones in my life. Or, I could rip them up and weave them into a wall hanging.

Do you see any similarities between the denim you love to wear and the shoes you love to make?

The shoes I make for my line are like denim in the sense that I try to design them to be timeless – they really should feel current wearing them today and five years from now. With denim and my shoes, you feel cool wearing them, but also exactly like yourself.

Do you ever think about denim trends when you’re designing your collections?

I do sometimes, because I design the kinds of shoes I want to have in my own wardrobe, and jeans are such a huge part of my wardrobe. All our shoes need to look good with jeans. I think about myself in jeans and then think about the kind of lift or vibe I want to have wearing them. That can inform the design of flatforms, or slides,  or chunky booties.

Have you ever made denim shoes?

I have tried to make denim shoes before. The tricky part about it is that so much of the part we end up loving about denim is the washes, and you can’t wash shoes once they are made. I once shipped the factory an old pair of my husband’s jeans to cut up and make some platforms out of. They looked incredible. Once we sold them we had to source a denim that looked distressed. Not easy.

Which are you more sentimental about, denim or shoes?

I am hugely sentimental about clothing and accessories in general, particularly about anything special my children have worn growing up. In my own wardrobe, I am the most sentimental about shoes because my line is such an important part of my life – it’s almost a chronology of my life.

Are there specific shoe styles you always wear with specific denim fits?

I feel like I look best in skinny jeans, so those are the only fit I really wear. I barely wear heels ever, most often I am in flats or semi-flat shoes. Heels with denim can look amazing but it’s a little too dressed up for me for every day.

Jessie Randall

What do your overalls and you have in common?

I would say I am pretty down to earth like these overalls.

What’s your favorite way to wear them?

I like dressing them up a bit with this Isabel Marant blouse. I also wear them with a plain old grey t-shirt from Alternative Apparel.

How many time a week or year would you say that you wear them?

I would say I wear them about once a month.

If you had to give them away, whom would you give them to? Why?

Probably to one of my friends. But these overalls are favorites of mine so I don’t see myself getting rid of them any time soon.

If you had to wear them forever, could you? Why or why not?

Probably not because I have a very small bladder!

Fill in the blank: In my overalls, I am _________.



To shop Jessie’s shoes and the entire Loeffler Randall collection, go to LoefflerRandall.com.