We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

If you lived through the aughts and don't care to reminisce on the infamous fashion trends — the very baby tees and low-rise jeans we shuddered at until very recently — odds are the photographic evidence has long been safely stored away, in physical photo albums or on memory cards in a drawer, somewhere, at your parents' place. But if you're Haylie Duff, you might come across pictures of your Y2K wardrobe during a random Instagram scroll, when a tag on an image from, say, the 2002 Teen Choice Awards may pop up. 

"Isn't it crazy that we look back on that as an era? We're so far out that it's a throwback," she tells me. "Oh my God, we're so old. I'm that old."

Duff is game to discuss those early 2000s red carpet moments, which left a mark on many impressionable teens and tweens, and are now being reintroduced into our sartorial lexicon. She's amused by it all. "I look at these young girls that are wearing basically everything we wore in the early '90s — when I was a kid, my mom was always like, 'You guys think you invented that, but we've been doing that since the '70s.' Now, I'm old enough to be like, 'Oh my gosh, I did that as a kid,'" she says. "It's funny how that comes around." 

Her style nowadays is much less heavy on the low rises and oversized belts, and much more about ease, versatility and longevity. Duff's a mom of two now, and an actor ("Blending Christmas," her new Lifetime holiday film, comes out Dec. 12), influencer (you can follow her at @haylieduff) and entrepreneur (she co-founded the made-in-L.A. childrenswear label Little Moon Society) — she thinks about fashion in relation to how it best suits her lifestyle. Ahead, she breaks down her modern-day uniform, shares some of her favorite recent purchases and talks about the pieces from the 2000s she's kept to pass down to her kids. Read on.

"I was actually [just] online shopping because I've got some stuff coming up. It depends on the event — [for holiday parties] I normally love pants. I love a good pair of trousers, or even just a good pair of jeans with a sparkly top. That's one thing that is pretty consistent about me: I'm very casual. I tend to lean more into a great pair of shoes, good jeans and a sparkly top for the holidays versus dresses. Or a good jacket — I always love a good jacket. I love Jenni Kayne's cocoon sweater. I live in it. I've got it in every single color. I can put it over a dress or a T-shirt and jeans; I can just wear it with so many things. 

"I have a charity event coming up that I need a formal dress for. I'm like, 'Oh my gosh, something formal? I feel like it's been forever since I've been to anything formal.' You know who I always love for dresses that are more formal but not super fancy? Black Halo — for a good, simple black dress that you can wear and people don't notice if you've worn it twice.

"My uniform just about every day is a pair of slim jeans, Isabel Marant sneakers and a Les Tien pullover, or a good white T-shirt with my Jenni Kayne sweater. I love the blouses from Ulla Johnson; anytime I'm going somewhere and need to put together something quick, I can always put on one of her shirts and people are always like, 'I love your top.' She's got great fabrics and prints. 

"I actually bought a jacket from Good American — it was my first time ever buying stuff from there — and I love it. It's this really thick military jacket, but it's made out of cotton and has a good hand feel. I'm going to live in it this winter. I also bought a brocade jacket from Forte Forte. I have nothing to wear it to, but I'm excited for the day that I get to wear it. It's hanging there as like, 'One day.'

"I have a pair of vintage Levis that I live in, and that's something I feel like I'm going to have forever. If someone takes them away from me, I'll be so sad. I have a military jacket that I bought about a year ago that I love — it's so broken in and soft, and I can wear it with literally anything. Then, I have a Chanel crossbody bag... It can be your special bag that you use for everything. My mom gave me a Louis Vuitton that she bought in the '70s when I was probably 15, and it looked like she had just bought it. Sometimes, you can make a larger purchase like that, knowing that it's going to last you forever if you take care of it, rather than having 20 other handbags that you rotate out all the time.

"I did some Black Friday damage. I did some Jenni Kayne damage. I did some Freda Salvador damage. I've really been on a furniture kick more than anything recently, but I definitely got in on some Black Friday sales.

"If you looked at early 2000s pictures, you know that 'simple' was not in my vocabulary back in the day. As I got older, and especially as I had kids, my time to spend on myself every day — how long I take to get ready and things like that — has gotten smaller, so I tend to reach for really good basics that I know [make me] look fairly put-together and like I put a little effort into it, but it didn't take that much. Stuff that I feel like I can do school drop-offs in, but then I could walk into a meeting if I needed to as well. I think also, as I've gotten older, I care a little more about quality versus quantity. It was a big part of my kids' clothing line, Little Moon Society, which was born out of all of a sudden, my awareness of what the fashion industry meant for the environment. I started being like, 'Oh, I think I'm going to maybe not buy as many things, but I'm going to buy better things.' 

"There are outfits that come to mind [from the 2000s] that I'm like, 'I cannot believe I wore that' — those come to mind a little more prevalently than the good ones. I went through a phase where I wore a lot of vintage. There's a vintage dress that comes to mind that was a black and one shoulder. Looking back, the choices that I made that were more simple have stood the test of time much longer than some of the crazier outfits that I wore.

"One of the things that I wore a lot were big bangles, and a lot of the ones that I had, I bought at vintage stores. That's a look that always sort of works — a great statement piece of jewelry never really gets old. I could wear some of them today and people be like, 'Cute.' 

"We could probably let go of the super, super low jeans. I also remember very big belts back in the day. Someone tagged me on Instagram recently for a giant belt. The jeans under dresses were also really funny. That was the jam... Like, 'the dress would've been fine on its own, Haylie. What were you doing?' 

"I have boxes and boxes of my old special things — my old designer heels or special designer dresses that I loved — packed away from my girls. My husband's always like, 'Do we need to keep five boxes of shoes?' I'm always like, 'When they're 20, they're going to think this stuff is incredible.' I hope we're the same shoe size, because they've got some real gems coming for them.

"When I was doing 'Hairspray' on Broadway, it was such a big life change for me at the time. I was in my early twenties. I moved to New York by myself for the first time. It's such a big deal to do that. I bought a draped neck Missoni mini dress. I wore it to something — I can't remember what it was, but I remember that purchase and being like, 'This is the greatest dress. Oh my God.' I wore it with these purple glitter Gucci pumps. I thought those shoes were the greatest thing that had ever happened to me. They're definitely packed away in my boxes for my girls one day. They're either going to think they're amazing, or they're going to be like, 'Mom, these are so not cool. I can't believe you wore these.'

"I see stuff I like scrolling through Instagram. I love the Popular page — I'll spend so long watching the most random Reels people post. I think I see stuff there probably more than anything. This whole new shopping thing on Instagram is a real problem for me. They're like, 'Oh, you like that? Well, here's 20 more things that are kind of similar.' And I'm like, 'Oh no.'

"One of the cool parts about this business in general is that when you're on set, you get to work with really talented people that know how to put things together and how to make a really great outfits seem effortless, which I think is the best kind of fashion. I hate when somebody follows every trend. I gravitate more towards people that have found something that works for them, and then just continue to reinvent that. I certainly have been inspired by wardrobers and people in the costume department on movies and how they put things together. But I also feel really fortunate that so much of my job and what people look to me for is me at home. I do so much cooking, I do a lot of recipes for different brands — that really is more of me in my home environment, and that really is in alignment with who I've morphed into fashion-wise, which is a little more low-key.

"I love online shopping from specific stores. I need returns to be really easy — that's the thing that will deter me from shopping somewhere. But as we've started to, knock on wood, hopefully come out of the pandemic a little bit, moving to Texas things have been a lot more open here. I actually have gone shopping into actual stores a little more than I was before, which I have to tell you, I really enjoy. I forgot how much I enjoyed that. My kids are both in school now, and some days I'll find myself just going off on a shopping day by myself. I put my ear pods in, listen to an audio book and hit up a Nordstrom. I'm like, 'Nothing can be better than this moment.'"

This interview has been edited and condensed for clarity.Please note: Occasionally, we use affiliate links on our site. This in no way affects our editorial decision-making.

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