Freemans Sporting Club - Sakiori Denim Studio Coat





A wise man once said,

"If you look for deals, you will find them."

It was me. I said that, and it's true. One of my favorite pastimes in recent years has been searching for some of the best values in menswear. But over time, I've found that the way I've come to think about potential purchases has evolved quite a lot, which I'd wager is the case for many. In the beginning, most guys (including myself) set out to just try and "dress better" in a completely nebulous and predominantly naive sense of the phrase. At this stage, you need almost everything - a basic upgrade of chinos, jeans, oxfords, sweaters, jackets, etc. But as your style matures, your scope narrows, and your closet changes, it may be appropriate to shift gears and reevaluate how you consider the items you buy.





Below is a set of questions I try and ask myself these days when I'm contemplating buying something. I've found it's led me to have fewer regrets and increased the amount of enjoyment I get out of the things I do choose to buy. If you've never thought about the topic yourself, it may be a good jumping off point for developing your own system for evaluating potential purchases.





1) Does this work with your style?





Early on, this question might not mean as much as it does after you have all your basics covered and start developing a more focused sense of personal style, with all its accompanying likes and dislikes. However, I think it's important to be brutally honest with yourself, even when a find is unbelievably cheap. I still make this mistake all too often myself. Ask yourself if this is something you can and will actually wear. If the answer is probably not, then it's probably not a good idea unless you plan on flipping it - an endeavor that is usually not worth the effort.





Kapital at Unionmade



2) If you pass on this, will it really bother you?

"Please, someone buy this." I've read that phrase and said it myself more than a few times when a deal was almost "too good to pass up" but I knew, deep down, that it didn't check all the boxes for me. More times than not when I've been agonizing over a purchase, if the opportunity is lost I've actually found myself feeling relieved. That feeling is the amygdala congratulating the frontal lobe for not wasting money needlessly.

On the other hand, there are times I've waited too long on when I shouldn't have and missed out on some amazing pieces that I still think about, but that's honestly just the nature of taking the sale game to the bleeding edge. That gorgeous Freemans sakiori coat pictured above is a great example of that - something I'm hoping I can still catch on the secondhand market down the line in coming months/years.

3) Does this fit an existing gap in your wardrobe?





So let's say your closet is already stuffed with navy chinos, do you really need to buy another pair? The answer may still be yes - after I bought my This is really more of a soft consideration than a hard and fast rule. The more you need something, the lower your threshold usually is to purchase. Conversely, if there's something you already own that's very similar, it should trigger some deeper contemplation about whether or not it's the right choice. I could very easily own everything in the Red Wing Heritage and Wolverine 1000 Mile lineup for somewhere in the realm of $100-150 each, for example - objectively a very good price - and yet spending $1000 on 7 or 8 pairs isn't likely to meaningfully increase the sort of fulfillment I get from just a couple.So let's say your closet is already stuffed with navy chinos, do you really need to buy another pair? The answer may still be yes - after I bought my Freemans Sporting Club sashiko jacket in Japan, for example, I bought a very similar piece in the same line off Yahoo! Japan Auctions not long after. But the times when I'll double or triple down on items that are quite alike usually come as a result of answering a resounding "yes" to the last point...

My Red Wing Beckmans



4) Do you love it?

I find this question to be the single most important thing I ask myself these days. Most purchases you have to ponder a little while, but there are those rare pieces that come along once in a blue moon that just floor you. Think Margot Robbie walking out of her bedroom in Wolf of Wall Street. Think Gollum with the One Ring. Think the first time you heard The Beatles - whatever floats your boat. Those times you just know, and the decision is simple (speaking of things I love, by the way, I've got a Kapital denim ring coat on the way that you should be seeing more of soon).





If anything, waiting for moments like these has helped me hold back on some less compelling sales, which ultimately saves money and space for something else I can really enjoy. If you don't really love it, take some pause to ask yourself "what's the point?" You may end up with another piece of ignored filler in your closet. Counter-intuitively, "saving" money on a great sale may actually be wasting more of it. That's why buying the perfect thing at full price can end up being a better value in the end sometimes.



My Bleu de Chauffe eclair bag (purchased at full retail)



So that's basically it, if perhaps in slightly overly simplistic brush strokes. In reality, the decision of when and when not to buy something is often much more complex and nuanced than a few simple yeses and noes, but I think it's a decent place to start. Do drop me a line and let me know what sort of things you consider, what works for you, or any other aspects I haven't discussed here that have been useful in your own purchases.