How to Find the Perfect Pair of Jeans for Your Body Type (From a Vintage Denim Expert)

Denim should be the easiest thing in our closet — we wear it almost every single day — but somehow it's the category that humbles us the most. We've all had that experience of walking into a department store, trying on ten pairs of jeans, and leaving with none. I'm joined by Lindsay Davidson Paley, founder of Lenny, the LA vintage denim store that has become a destination for anyone looking for their perfect pair. After spending an afternoon in her store and walking out with jeans I actually love, I wanted to sit down with her to demystify everything about denim — from why fit feels impossible right now, to what to actually look for when you're vintage shopping, to the conversation you should be having with your tailor. In this episode, we get into: Why finding jeans that fit feels harder than ever (and the fit model problem nobody talks about) Vanity sizing and why you're a 24 in one brand and a 26 in another The single most important thing to know before you shop for jeans (hint: your measurements) Why Lindsay's a firm believer in dressing for your body — and the one rule jeans don't get to break The Levi's 501 lore: why everyone wants them, why they don't work on everyone, and how to actually wear them The viral "size up three in the new 501s" hack — and whether it actually works The three non-negotiables Lindsay looks for when sourcing vintage denim (original hem, wash, distressing) Why the original hem is sacred and what to tell your tailor so you never lose it The case against skinny jeans (and why America is the only country that agrees) Why a dark wash is the most universally flattering and elevating The crotch test — Lindsay's tell for whether a pair of jeans is actually right for you How to know when a pair is workable for tailoring vs. when to put them back Whether $700 jeans are worth it and what you're actually paying for The best modern denim brands worth investing in (Agolde, Citizens, The Row's Yale Alaw, Khaite, Reformation) The best pregnancy jean (and the Levi's Low Loose nobody can stop wearing) Why denim is officially a neutral — and what it says about fashion that Chanel, Celine, and Gucci are all sending jeans down the runway Plus, on Let's Get You Dressed: what to actually wear to a spring baby shower when you're not a floral dress girl Connect with Lindsey Davidson Paley: Instagram: Thank you to my partners at Macy’s for my newest wardrobe essentials. Shop my selects here! Let’s Get Dressed YouTube: Instagram: Newsletter: Liv Perez Instagram: TikTok: ShopMy: Hosted on Acast. See acast.com/privacy for more information.

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How to Find the Perfect Pair of Jeans for Your Body Type (From a Vintage Denim Expert) is an episode from Friend of a Friend by Liv Perez.

This episode is 46:56 long.

This episode was published on Jun 1, 2026.

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