I will be the first to admit it: I buy a lot of clothes. I try to budget myself, and I try to be as reasonable as possible, but one way or the other I buy a lot of clothes. With the fashion capital of the West Coast, Union Square, one BART ride away, countless thrift stores in Berkeley, and the Internet close at hand, I always end up emptying out my wallet and having to find new space in my closet. To be frank, it’s a natural part of the life cycle of the menswear geek. You’re first in it for the “timeless style,” not the brands, and operate under the assumption that men’s fashion has not changed that much in the past half century. You envision a solid wardrobe that is heavily reductionist: you need that one good pair of denim, one good suit, two pairs of dress shoes (one black and one brown).

“Buffalo Exchange had too much J Crew today.” The struggle is real, my friends.

But somewhere down the line, you grow keen to the details. You now need a dark brown wingtip oxford and Allen Edmond walnut monkstraps, not just a “brown shoe” (maybe double monkstraps). You are not sure if you want a double-breasted or a single-breasted suit, so why not both? And why doesn’t your wardrobe have camo or floral yet? Your taste is going to evolve, and you won’t even notice it, and that’s where you’ll find yourself in trouble. That’s where I’ve found myself in trouble. I always think that whatever I’m buying is “that one last piece” to whatever my original end-goal for the perfect wardrobe was. Let me tell you right now that it’s not, whatever it is. That’s why I have a maroon Brooks Brothers tie with birds on it, a Banana Republic Mad Men plaid blazer, and way too many sweater vests. Are they pretty cool? I’d think so. Are they necessary? I’d be hard pressed to say so.

It may be too late into the game for me, but to anyone who’s recently began to dabble in menswear, I strongly encourage you to start off on the right foot. I’m not saying, “don’t get into menswear,” because let’s all face it, suits are cool and ties magically improve every outfit. But keep conscious of your budget. I’m also not saying that you’re going to have to start shopping at Walmart and Ross and Goodwill (although that’s definitely a fun option), but it’s all about making each purchase really count. You can have your Banana Republic, and your Allen Edmonds, but make sure that everything you buy really is a meaningful addition to your closet. Here are questions that you should ask yourself every time you go shopping from now on:

1. Does this work well with the rest of my wardrobe?

A great way to prevent yourself from purchasing that next hella-trendy pair of camo pants or that ultra-preppy cricket sweater that might just kill your week’s budget is by asking yourself how many outfits you can really make with that one piece. If you can only think of about one, then put it back on the rack, my friend! You have to stop assessing each piece in isolation. Take colors for example. Why do we wear blue jeans so much more often than any other color? Because blue, especially any sort of dark blue, is incredibly versatile and works practically with anything. Burgundy pants? Not so much. Anything hunter green that would’ve looked fine with the blue jeans would look Christmas with the burgundy. In talking more about color, you’re going to find that certain colors are generally easier to work with, possibly even more “fashionable” than others. Neutral, muted, and earth tones, especially of blue and brown, come to mind. That’s not to say that everything you buy has to be neutral in the boring and bland sense. That’s where style comes in. Let’s say that you do prefer browns, beiges and other earth tones. Burgundy would work fantastic as a loud pop of color to contrast with the earth tones. It’s a two way street: having a more mature style leads to smarter buys, and smarter buys will then pave the way towards mature style.

Why ???

2. Would I have worn this two years ago?

Trends are an incredibly touchy subject in the world of clothes and style. On one hand, trends are probably one of the most significant and treacherous causes for wasteful spending and bad buys. For instance, due to reasons that remain unfathomably bizarre, just last year cargo pants made a comeback from the sartorial hell hole that was the 90s and took malls by storm. For hundreds of dollars you could have your own pair of designer, GQ-endorsed cargo pants everywhere from Gap to Barney’s New York. What the hell, right? You might have been able to wear those cargo pants maybe until November last year.

That’s not to say trends are evil. In a community that constantly pushes for creativity and uniqueness, fashion would be old news and maybe even a bit boring if it were not constantly reinvigorated with fresh ideas. Pocket squares, floral prints and monk straps are some retro-throw backs that come to mind that were each mini paradigm-shifters in its own right, and they’re each here to stay. The problem is, there is a difference between trends that are meant to help you reinvent your style and trends that are merely meant to give you something new to buy.

You’re going to have to figure out which is which. So, you have to ask yourself, would the “you” from two years ago have considered this trend stupid? If yes, then the “you” two years in the future would probably also have to agree. On the other hand, if you could imagine yourself wearing it two years in the past and in the future, then go ahead. You are probably not just swept in the hype of the now. Once again, camo pants? It was for dorks just back in 2011. Good idea? Probably not. Chambray shirts? They’re very GQ right now, but you could have just as easily pulled it off two years ago.

3. Did I want this before I came into the store?

One way I exercise constraint when faced with a tough decision at the store is by constructing a “master wish list” before I go shopping and only buying whatever is part of this list. That way, if I ever do splurge on a single item, I can be for sure that I won’t experience buyer’s remorse the next day, because there was no impulse and suddenness involved in the decision. Furthermore, by deciding what you want before you shop, you can really begin to construct a well-curated wardrobe rather than a random assortment of apparel.

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