The 5 Best Investment Pieces in my Closet - Lollipops & Laptops

I’ve never been one to go full throttle on the latest trends. If I had to describe my style, I’d call it California Prep–casual and classic. I could live in jeans and a t-shirt if I didn’t work in a corporate setting. Over the years, I’ve worked out a few of my favorite brands and I tend to stick to them. They’re usually mid-range brands that can be found a Nordstrom or local boutiques. And while the quality is decent enough, I have found that in many cases, either the fit doesn’t stay relevant or the piece starts to fall apart after high use. In comes the investment pieces.

From the perfect coat to the ultimate statement bag, it’s easy to feel overwhelmed with the cost of true “investment pieces” for your wardrobe. For some, it might never be an option. Some people think they are worth saving up for. For a lucky few, they aren’t investments at all. But for me, there are five pieces in my closet that I have invested in over time and have been worth every penny, based on longevity of style and quality. Read on for what they are, how much I paid for them, why they’re great, and a decent budget-friendly option if it’s just out of the question for you but you want to hone that California Prep style.

The Perfect Blouse

The 5 Best Investment Pieces in my Closet - Lollipops & Laptops

Between my casual style and corporate day job, I have rarely found a piece that I can wear during the week and also on the weekends. But this top legitimately looks as good with jeans as it does with slacks. You know it’s a good find when they’re still selling the same blouse in the same silhouette nearly a decade later.

The 5 Best Investment Pieces in my Closet - Lollipops & LaptopsBrand: Joie

Purchased: 2011

Price I Paid: $195

Current Price: $208

Budget Alternative: Check out this blouse for a similar look. Best part? It’s hand washable (aka the hand wash cycle of the washing machine) versus my dry clean only version.

The Statement Bag

The 5 Best Investment Pieces in my Closet - Lollipops & Laptops

I joke that I paid 7.25% interest over 6 years for this bag because I was living off of student loans for law school at the time and it took 6 years (at 7.25% interest) to pay them off in full. It’s a good lesson in what not to do. In any case, I purchased this bag when I was in Paris at the Chanel store on Rue Cambon and it felt so right to buy it there. For the record, I take insanely good care of bags, so this one is in mint condition and lives in its dust bag inside its original box. The price for these bags have gone up so much (nearly $6,000 now!) that this is arguably one of the best investments I have made (if I’d ever be willing to part with it, that is).

The 5 Best Investment Pieces in my Closet - Lollipops & LaptopsBrand: Chanel

Purchased: 2007

Price I Paid: $2,500 (€1,740)

Current Price: $5,900

Budget Alternative: I don’t subscribe to buying fakes–they’re poor quality and tasteless (and illegal!) so if Chanel isn’t in your future, opt for a nice Rebecca Minkoff bag or skip the brands altogether and hit Target for a steal.

The Red Heel

The 5 Best Investment Pieces in my Closet - Lollipops & Laptops

I wanted these babies so bad as a new lawyer, so I split the cost with my then-boyfriend (now husband). They are a classic and go with everything, but I needed to put a little cushion at the heel to help keep my feet from slipping out of the low-cut heel. (The shoe salesman at Neiman Marcus had them on hand so it seems like a common problem). As I’ve gotten older and more practical, I have fewer reasons to wear them. Still, there’s something so special about that little peek of red when you put these pretty ladies on. Although the rounded toe is more outdated today, they are still on point when paired with jeans or a great power suit.

The 5 Best Investment Pieces in my Closet - Lollipops & LaptopsBrand: Christian Louboutin

Purchased: 2009

Price I Paid: $675

Current Price: $695

Budget Alternative: Again, I’m not a fan of look alikes, so I’d go with just a great classic black pump here. These are my go-to for daily wear that hold up great and are reasonably priced. I have them in nude and black.

The Work Bag

The 5 Best Investment Pieces in my Closet - Lollipos & Laptops

One of my more practical purchases, this bag is used every day for work and doubles as a carry on whether I’m throwing a book and sweater for grown up travel or stuffing diapers and toys in it for family vacations. The nylon fabric is super durable and there are just enough pockets/sections to be organized without being able to hoard.

The 5 Best Investment Pieces in my Closet - Lollipops & LaptopsBrand: Tumi

Purchased: 2018

Price I Paid: $395

Current Price: $395

Budget Alternative: There are so many options when it comes to laptop bags. If you really want a brand name, Longchamp makes a great, classic nylon bag. It doesn’t have all the organization (just one small interior pocket) and it will only fit smaller laptops, but it’s another classic at less than one third of the price. For a deal on a nylon tote bag, check this one out.

The Timeless Necklace

The 5 Best Investment Pieces in my Closet - Lollipops & Laptops

To be fair, I didn’t personally purchase this–my husband did as a gift for our wedding day. But as a classic piece that is nice on its own and still looks great layered with trendier pieces, I find myself wearing this as much with a suit to the office as I do with a dress for date night or jeans and a t-shirt at the park with my kids.

The 5 Best Investment Pieces in my Closet - Lollipops & LaptopsBrand: Tiffany & Co.

Purchased: 2009

Price I (He) Paid: About $2,000

Current Price: $3,100

Budget Alternative: Diamonds and brand are what makes this pricey, but for an everyday look, choose a delicate pendant like this one from Swarovski or this one (only $25!).

What have been your best investment pieces and what are you eyeing as your next investment for your closet?