15 Investment Pieces You’ll Never Regret Spending On

By Jenn Rose Smith

If there’s anything more embarrassing than wearing a midriff-bearing cashmere tube top and sweater combo, it’s having paid way, way, way too much for it as well. I should know, because I did it circa 1999. I was in the first years of shopping for myself without parental approval, and let’s just say Bebe was the scene of many of my early crimes. Fortunately we live and learn, and while I still make fashion mistakes here and there, I’ve streamlined most of my spending into classic items that I know I’ll get at least 5 years out of. Spending money on a quality product actually feels good, especially when you know it will serve your lifestyle well. Take it from someone who’s learned it the hard way — these are 15 items you won’t regret.

featured image via chuan song

A camel trench.

We’re swooning over this one from Acne Studios but don’t get mad — we also love this more affordable version from Suncoo.

A classic LBD.

It’s still on pre-order, but we’re in love with this little number from Emerson Fry.

A pair of knee high leather boots.

Trends in heel height and toe shape are constantly changing year-t0-year, but this conservative design from Sam Edelman should stand the test of time.

Aviator sunglasses.

This is one product where it feels “right” to splurge on the original classic — a well made pair of Ray Bans.

A classic pair of Levi’s.

Speaking of true-blue brands, it doesn’t get more original than a great pair of Levi’s in a classic fit. Let’s face it — all other jeans are derivative.

The perfect black leather pump.

For weddings, funerals, job interviews, third dates, and everything in between.

A good leather jacket.

Whether it’s a slick bomber or a Ramones-eque moto jacket, you’ll get many years of wear out of a good leather jacket. We’re digging this one from Free People.

A simple cuff bracelet.

Simple cuffs and rings in sterling silver will always be cool in our book. We love the designs of Charlotte Cauwe, who we recently featured along with her girlfriend in our It Couple series.

A good weekender.

Nothing makes you feel like you have your sh*t together quite like carrying a nice bag through the airport. At under $80, it doesn’t get much better than these vegan faux leather bags from Sole Society.

A straw market tote.

It’s a shopping tote! It’s a pool bag! It’s your favorite piece of home decor! You’ll find endless ways to use a classic straw tote over the years to come. We like this one from the gorgeous site The Cook’s Atelier.

A chambray shirt. 

Perfect for concerts, cookouts, and just looking cool in general. We love this tailored western shirt from Levi’s.

A neutral clutch.

Instantly dress up any outfit by carrying a purse without a strap. We like this blush envelope clutch from Rebecca Minkoff.

A crisp white button down.

Doesn’t get much more classic than this. But you’ll wear yours more if it’s well made with a flattering fit. Why not buy yours from a shop that specializes in nothing but crisp white button downs?

A simple solid colored one piece. 

No matter what your fitness future holds, you’ll look great summer after summer in a simple one piece like this one from Solid and Striped.

A white shirtdress.

One word: versatility. Dress it up with giant cocktail earrings and an updo, or wear it unbuttoned low to the beach with your favorite pair of flip flops. We’re loving this classic tie front dress from DVF.