When Should You Spend and When Should You Skimp?

A few weeks ago I got a turtleneck for cheap from Banana Republic. It proudly states “Made with Italian Yarn,” which is hilarious, because it’s 20% nylon (do Italians make the best nylon?). However, that didn’t bother me because it was inexpensive, it fit well, and it was exactly what I was looking for.

We’ve all got a certain budget we’re working within when buying clothes. Some folks have a larger budget than others, of course, but everybody has to make decisions about what they will drop a ton of money on versus what they’re okay buying for less. For me, I’m always thinking about opportunity cost. While I’d have preferred, say, an Eidos turtleneck for its superior construction and material, the cost (nearly 10x) simply wasn’t worth it to me. Now I’m planning ahead to know what spring purchases I will use that extra money for.

While I don’t have a flowchart or anything, here are some questions to ask yourself in order to maximize the use of your dollars when building your wardrobe.

First, have a working list of what the ideal wardrobe for you would look like. It should mostly be the “must-have” items that you’d wear regularly, but it’s also okay to have stuff that delights you. This list can help you keep track of progress made toward attaining a good working wardrobe, and also keep you from making costly mistakes. I wrote more extensively on this concept in my article How to Create a Capsule Wardrobe and Making Smart Menswear Purchases.

With that in mind, then, here are questions to ask yourself:

What is your lifestyle? The utility of any given item is defined by your lifestyle, meaning what you have to wear day to day will play a huge role in what makes sense to invest in. This can go both ways, actually—for instance, if you need to wear a white dress shirt every single day to work, it can make sense to buy a bunch at low cost when you’re first starting out, knowing that the regular wear and tear will take its toll on them. But as you increase your rotation, adding in nicer, better designed, better made shirts as your budget allows makes sense because of your needs.
How do you like to dress? What is your style? Most of us have clothes we reach for time and again when we are dressing to impress. It makes much more sense to spend extra on stuff you know you’ll wear a lot (and in particular that which will be seen a lot), than it does for things you’ll primarily be wearing to bed.
What kind of design are you looking for? Designers typically continuously tweak, evolve and update their line to stay fresh. That can be good if you’re someone who’s already got a good working wardrobe and are now just buying clothes because you like them—you can be open to being surprised by something interesting. But sometimes that’s not good because you just want a stylish basic to fill a need in your wardrobe. I was excited to find that Banana Republic turtleneck because it met several specific criteria I had that I couldn’t find anywhere else within my general price range—thin enough to layer but with visual surface texture and a ribbed neck.
How long do you honestly think you’ll wear it? Is it a “forever” piece or something you know is a just a phase you’re going through?
Is it outside your comfort zone a little bit? Maybe you’ve been inspired by someone’s sweet fit on Insta, but aren’t quite sure if it’ll work for you—finding it for cheap somewhere is a good way to dip your toe in to see if it’s “you.”
Is there a dramatic quality increase from the budget options to the expensive options?

With the buying and selling forum, eBay, etc., it’s possible to get high-quality stuff for much lower prices—if you’ve got the patience and time. But especially when you’re starting out and you need to build a wardrobe fairly quickly, asking yourself these questions can help you decide what to save up for and what’s okay to buy for less.

Below are some products (including that turtleneck) that I personally own or would buy that run the gamut from expensive to not so much.

Banana Republic turtleneck.

Barbour Ashby: I’ve been inspired by cool dudes like Jake Grantham rocking the Barbour over tailoring, and there is really no substitute for the original. This, to me, was worth spending more on for the authentic original.

Navy/Gold repp stripe tie, PoloRL: Navy/gold bar-stripe repp ties aren’t hard to find, but I liked the specific color of gold Polo used.

Brooks Brothers light blue OCBD: OCBDs are a staple for some guys, and while Kamakura, Proper Cloth, O’Connell’s, Ratio, Mercer & Sons and millions of others make good ones, the shape and complete lack of lining of the collar from Brooks Brothers—in addition to the consistency of availability and generous return policy—make this a good choice. I prefer this lighter blue color, but they offer tons of other options. Just make sure to stack discounts (you can browse the Official Sales Thread to find the newer ones).

Eidos Navy donegal blazer.

Eidos large glen plaid suit: There is no substitute for Eidos as designed by Antonio Ciongoli for me—the swooping arc lapels, the Neapolitan details, the killer fabrics, not to mention a near-perfect fit on me. When you find a winner, you stick with it as long as you can.