You’re Shopping For Shoes Wrong (According To This Shoe Expert)

It would be really easy to be frenemies with Jessie Randall. The cofounder and creative director of Loeffler Randall — the fashion-girl-approved shoe and bag company that’s stocked at holy-grail retailers including Bergdorf Goodman and Barneys — has been running her lucrative business for a decade, nabbing a CFDA award along the way. Plus, she owns hundreds of pairs of shoes. (Ugh.) But then you think of the possible perks of knowing her. (What’s a sample size in shoes, again?) And on top of it all, she turns out to be a genuinely likable, badass person. Such was the case when we caught up with the girl boss at her office in Soho, where we grilled her about everything that matters when it comes to buying and wearing shoes. Not surprisingly, the woman who launched her own line because, she says, “I couldn’t find the exact pair of shoes I wanted to wear,” starts her outfits from the ground up. Read on for Randall’s shoe-centric insights on pulling the trigger regret-free, how to tell they’re “the ones,” and why you should buddy up to an old-school cobbler, stat. Then head over to Gap, where the style conversation continues. We won’t blame you for forgetting all about the “-enemy” part. Okay, straight up: What’s the secret to shopping for a great shoe?
"Finding a brand that fits your feet really well is important, especially for fall, when you end up buying investment pieces that you're going to wear for a really long time. The next thing is the quality of the materials. Check inside, look on the outsole — it should be easy to tell when something is synthetic versus real leather. Put your hand and your foot in there to see if there's adequate padding. And inspect to make sure the stitching is beautiful and everything is done in a high-quality way." So is having to break in a new pair a deal-breaker?
"Even really nice shoes can take a little while to break in. Go slowly — it takes a bit of time to get them to mold to your feet. That’s normal. But you really should only be shopping for shoes at the end of the day when your feet are swollen. That’s a good way to get a size that fits you well. People’s shoe sizes change over time and all people have a different-sized left and right foot, so it’s important to get your feet measured."

How about care? Are you a special-storage freak?
"I take terrible care of my shoes because I get a lot of them [through work]. But you can put them in the bags they come in and keep them out of the sun. And you can stuff the toes with tissue paper once you put them away for summer or winter, so they stay in the right shape. It’s also great to take them to a really good cobbler you trust at the beginning and end of the season. Talk to them about how to help preserve your shoes. You can say you plan on wearing these everyday for the rest of fall and ask, ‘What can you do? Can you treat the leather so they stay clean longer? Add on to the sole?’"
If you don’t happen to own an accessories company, how do you build a well-rounded shoe collection and make rent?
"For fall, it’s great to get a go-to bootie that you love, can walk around in, and will wear with everything. I like something more flat for everyday. A pair of rain boots is good to have, as is a basic pump. A pair of sneakers is another versatile item. What’s great is that you can wear them with something really casual like jeans or with a little miniskirt or a minidress — it looks really cute. You can’t really go wrong."

When is it worth it to splurge?
"Obviously, your wedding is when you should spend a lot of money on a pair of shoes. Around the holidays is also when I'll buy something a little more dressy. Or sometimes you just find something that makes you really excited the second you see it, and you have to get it. That’s when you know it’s worth it. Seasonally, it’s fun to add that 'wow' piece to your wardrobe."

What’s your response to the conundrum of wearing killer going-out shoes, only to kick 'em off in pain at the party?
"I don’t think you have to go super high to be dressed up. I don’t like to be too dressy or too casual — I kind of like the middle space, a mix. We have this 90-millimeter pump that I end up wearing any time I go out. It’s so comfortable, people tell me all the time, ‘I never wear heels, but I could wear this all day long and be fine.’ There are really great heels out there that are a bit sexy but aren’t killing your feet — cute kitten heels or a heeled bootie."
Any shoe sins that make you cringe?
"I don’t think there are hard and fast rules for what you should and shouldn’t do. I see people wearing shoes that are very cheaply made, which maybe haven’t been produced in the nicest conditions. I feel like, you are walking around in those everyday; you should invest in something that is going to take care of your feet. I like to know that I’m getting something higher quality and made with care. So for me, it’s just thinking about fit and quality." What’s your advice for avoiding purchases you’ll be sick of in a year or two?
"I’m always thinking about that when I’m designing. We want this product to be in your closet for a very long time. We don’t want you to look at it and be like, This is so last year. Especially with something that can be a little more expensive, it’s important to think about all the occasions in your life, making sure there's a lot of versatility. A style you can go to the farmers' market in but also wear with something dressy? Those types of shoes are the ultimate because you get so much use out of them." BTW: On top of looking and fitting great, the jeans featured here were made by women who participate in Gap Inc. P.A.C.E., an education program that offers them the opportunity to gain life-changing skills and confidence. Gap has committed to expanding the program — which is now active in 10 countries including India, China, Indonesia, and Bangladesh — to reach one million women worldwide. Meet some of these women and read their stories at

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