5 Fall Personal Style Pieces I’ll Always Splurge on and 3 I Never Will

I don’t have many hard and fast rules when it comes to personal style or shopping. But one thing that I’ll always stand by is that you should buy the best version of the wardrobe workhorses—the pieces you know you’ll wear time and time again—the first time. Skip the approximations. Skip the dupes. Buy right and you’ll rarely have to worry about it again. Hence, this week’s newsletter about the pieces I’m always willing to spend money on and ones I’m fine buying on the cheap.

Items I’ll Always Splurge On

Pants

If you’ve been reading this newsletter over the past year (thanks <3), this should come as no surprise: Nili Lotan and Dries Van Noten make my absolute favorite pants. They are unequivocally a splurge. But after years of trying to Goldilocks myself into trousers that are only okay, I finally cut the BS and dropped some cash on the pants I know will always work for me. I’ve regretted many clothing purchases in my life, but pants from these two brands are not on the list.

Boots

I hold onto my shoes—especially my boots—for a long time. And since I’m in New York, I need pairs that are comfortable and can take daily wear and tear from all the walking I do in one day. I’m fine with spending money on boots that I’m sure I’ll want to wear for many seasons (the benefits of not buying into trends unnecessarily) and then taking them to the cobbler should I need any repairs. The ones I actually own are no longer on sale because, well, they’re old, but below are some new season versions I recommend.

Jewelry

Believe it or not, I’m allergic to costume earrings. They do a number on my ears, so I kind of have no choice but to wear gold vermeil or solid gold. Luckily, this aligns with my overall approach to wearing jewelry—which is to wear the same good stuff every single day. Then, it becomes a signature! Pro tip: If you’re ever in Beverly Hills, swing by XIV Karats LTD, a no-frills jewelry store that has incredible gold and diamond jewelry at really low prices.

Items I’ll Always Save On

Jeans

I don’t believe in spending hundreds and hundreds of dollars on denim. Not to yuck anyone’s yum, but it’s just not for me. Sure, jeans can be annoying to shop for, but I don’t think you need to throw money at the problem—you need time. Try on many, many, many pairs to find the ones that work for you. And start at Levi’s! Over the past few years I’ve found so many pairs in both the men’s and women’s sections that I love and that cost under $100.

Jackets

Chore coats, barn jackets, and field coats are currently super-trendy, but they’ve been around for years. That’s why I believe in going straight to the source rather than buying the designer version of them—hence my love of Carhartt and Barbour. Affordable and made to last. What’s not to love?

White T-Shirts

Uniqlo, J.Crew. Gap: My go-tos for the last 20 years.

Bonus Category: It Just Depends…

Bags

I’ve spent thousands of dollars on bags and hundreds of dollars on bags. It really just depends on the item and my visceral reaction to it. If it elicits an I MUST HAVE IT reaction, well, I must have it! Coach, as I’m sure you’ve heard, is so back with tons of great options for less than $1,000. If you’re looking for a new bag that will stand the test of time, start there.

Sweaters

behind Discovering &Daughter last season was an absolute revelation and a game-changer for my sweater wardrobe (the fit is perfect). But that doesn’t mean I’m leaving my tried-and-true J.Crew cashmere crewnecks or Alex Mill wool jumpers.

First time reading Self Checkout? Catch up on the past few weeks.