As guys, our wardrobes are far less subject to trends. The cut of our denim and the width of our ties seem to be the only variables for the most part, unlike our female companions, who face the whims of fashion head-on. The good news is that this means that we can buy better rather than more often, because the pieces we buy will last longer. Or they will if you're willing to prioritize. Before I go any further, a working definition of "splurge": this is not the sort of thing that happens in a makeover montage in a chick flick. It's not about fashion, or brand, or even about price. It's about quality. Threadcount and fit instead of logos and flash. Which is not to say that the manufacturer is unimportant, but make an informed approach. There's a huge difference between Polo made in China and Polo made in Italy.

So, what should you spend your hard-earned cash to wear (hopefully for a long time)? First, look at what you wear daily, to work and after. This will determine a lot your responses below.

Pants. Whatever sort of pants your job requires you to wear daily is worth a splurge. You'll have fewer pairs of pants than shirts, so you'll spend more time in the pants you do have. If you wear jeans, get quality jeans. Selvedge denim will stand up to a lot more punishment than cut and sew fabric on cheaper jeans. Look for reinforced stitching on the inside of the legs, and heavyweight fabric. If your office demands khakis or dress slacks, invest here, too. As much as I love Dockers' D-1 slim fit, they can't hold a candle to the Gio from UNIS: American made with Italian fabric, slim but not skinny, and with odd-numbered sizes for a perfect fit. $180 sounds like a lot for khakis, but when they'll last and look fantastic for the whole time you own them, it's a no-brainer.
Sweaters. Just kidding. While a nice cashmere sweater is a beautiful thing and worthy of investment in colder states, if you're living in a place where it only dips below 40 for about five days each year, spend elsewhere. Get a cotton sweater at J. Crew or where ever, and use the rest of your money for those khakis.
Outerwear. Regardless of how heavy of a coat we're talking here, well-built coats will last a long time, and will be largely trend-resistant. Find a good pea coat, trench coat or parka in real wool or waxed cotton instead of a man-made fiber, and let it wear until it falls apart. Which will take a long time. I bought two Barbour jackets this winter, and I don't think I'll buy another coat for 15 years. Seriously.
Suit. Notice I didn't say suits. Even the most casual guy needs a baller suit that he can bring out when the occasion demands it. Get navy or charcoal, not black. (Because you're not a waiter or a funeral director) No stripes, no plaid, no super skinny lapels or superfluous details, since you're keeping this for a while. Fortunately, quality suits are easier to find than you'd think. Scour a good Marshall's for something Italian, or find one of the many new online bespoke (custom) tailors to make one to your exact measurements. Don't feel like you have to spend a grand to make this happen; just get something worth a grand.
Blazer. Again, singular. A navy blazer is as versatile as a pair of jeans. Skip the polished brass buttons, look for something fully canvased (meaning that a layer of canvas is built into the body of the jacket, making it conform to your body better), get it tailored well. Wear it with any pants, any shirt, any tie or no tie. Wear it to breakfast, lunch and dinner. I'd almost be tempted to spend more on this than on the suit.
Shoes. The difference between quality shoes and cheap shoes is probably the most striking of all of these items. Compare full grain leather to corrected grain, and even the most untrained eye will notice the difference. Get one good pair of brown shoes that fit you really well, and are Goodyear welted so that they can be resoled when they wear out, and you should be able to keep them for a decade or longer with proper care. Budget $300 or more (seriously) and then wear them enough to ensure you're getting your money's worth. And when they're really worn out, the best brands (Allen Edmonds, Alden) have a refinishing service that will restore the entire shoe back to an almost-new condition.

Finally, note what was not included in this list. Shirts. Ties. Socks. Sneakers. All of these can be expensive items if you get tempted to spend, but it's much harder to justify the cost when you're talking about items that are some of the least durable and most subject to trends available. When it comes to these items, get stuff you like. Get it on sale. And shed no tears when it's not cool anymore or it wears out. Donate to charity, throw it in the trash and move on.

The other benefit to this sort of wardrobe is that it will age along with you. No matter how old you are now, you'll want to dress appropriately for your age. With conservative pieces like these, you'll look just as good as you move into your upper 30's as you do in your 20's, without looking like an old man now.

-Rob Hays

Rob is sitting in for Alex, and has written about menswear for AVE Styles before. He's also this guy.