Let’s be honest here: some things are worth the price, while some could be skipped entirely.
Here are some items you should spend a couple extra dollars on, and some others you can skimp on and still come out okay.
Splurge on these if you have the cash
You can find “dress shoes” practically anywhere (even Payless has stuff that can pass for decent “dress shoes”, or something that resembles a leather shoe), but there are vast differences between a pair that costs $39.99, $300, and $1600. And yes, there are shoes that cost $1600.
Where do the differences lie? Material (leather vs faux leather), quality of the material, the sole, construction, finishing, and so on. For a decent leather shoe, you’ll want to stick in the $200-$300 range and up. Alternatively, if you’re a slick bargain hunter, you can scour eBay or Style Forum for brands that typically sell models in that price range and buy them at a discount (albeit slightly used in most cases).
I found a pair of used Antonio Maurizi double monk straps in a tan leather for $120 online. These usually retail for $300. Granted, it took a while and I had to be patient in looking for that particular shoe, but if you have that kind of time you can find some great deals online.
I also have a pair of burnished brogue boots by Harris that my lovely girlfriend got me for Christmas. She found them on sale at Barney’s for $275, but their retail is around $600. Deals are plentiful for the patient shopper.
A classic watch
I can’t wait to amass a collection of watches like John Mayer, but until then, I’m setting my sights on an entry-level piece that’s classic and goes with everything.
I appreciate watches more than I do clothes, mostly because it’s a different ball game with a higher barrier to entry. Sure, you can buy a $500 pair of Alden shoes and learn their history, but to know and appreciate (and be able to afford) the mechanics of a tourbillon, for example, is something completely different.
As far as classic, entry-level watches, I’m thinking of pieces like the Cartier Santos, Rolex Air King, IWC Portofino, or the Tag Heuer Monaco. Sure, it’s good to have a Timex as your everyday watch, but as your disposable income grows, look into investing in one of these. Soon it will turn into your everyday watch, and maybe even become an heirloom you pass along to your kid one day. How cool would that be!?
A great suit
Just like shoes, there’s a big difference between a $200 H&M suit and a $6000 Ralph Lauren Purple Label suit. That’s a whole article within itself, but a lot of the differences lie in the construction and fabric alone. If you’re interested in details, check out my friend Antonio’s explanation here on Quora.
The price of the suit isn’t as important as the way it looks on you, so no matter the price, always take it to a tailor.
Assuming I was rolling in dough, however, I wouldn’t mind spending top dollar for a nicely made suit, crafted from some fine wool cashmere, like RLPL. Besides, if you DO have that kind of money, you’ll probably find yourself in a bunch of situations where suiting is necessary. That’s how I picture it, at least.
Save your money; don’t bother spending top dollar
T-shirts, socks, and underwear
I find it a little crazy that Calvin Klein sells ONE pair of boxer briefs for close to $30. Do they last five times longer than the Hanes boxer briefs that I get from Target? As far as I can tell, they’re pretty comparable, save for the branding on the waist band.
Tees as well. I’ve seen T-shirts for $50 and up… for a plain, white tee. Why?
Stick with the basic brands you see at Target, or a 3-pack you find on sale at Macy’s. You don’t need a $50 t-shirt. One brand I do like (that can be pricier than something you’d find at Target) is American Apparel. They have great-fitting tees in super soft jersey cotton.
I’ve mentioned this before, but I’ve never spent more than $50 on a pair of jeans. I stick with dark-wash, unadorned, straight leg denim from Levi’s. If you’re the John Mayer of jeans, and you’re all about the selvedge 20 oz Japanese cone mill blah blah blah that goes for $300+, I can respect that.
For the everyman, however, try a pair of Levi’s 514 and see how you like those.
Bird legs? Levi’s 511. Thighs bigger than your head? Levi’s 501xx Shrink to Fit.
So these are my thoughts on what I find acceptable to spend a little more coin on, and what I feel can be skipped.
Agree or disagree? Let’s hear it in the comments below.
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