As I clicked back through The Style Guide archives to prep for this post, I realized it had been far too long since we’d covered stylish men’s dress shoes on the blog. Like, nearly two years too long! A lot can happen in two years, folks. Of course, what can also happen in two years? Nothing at all. As in — if you buy an investment-worthy pair of men’s dress shoes from the below list,  you’ll be able to wear that pair frequently, day after day, with no need to trade ’em for a new pair. That’s the beauty of buying quality and paying a bit more, as you’ll see from the below list. We aimed for a mix of versatility and utility throughout the seasons — whether you’re suiting up for winter or dressed in classic spring style, the below picks should cover you for situations where you need to look sharp and feel comfortable. And with situations like spring and summer weddings come up, a dress shoe refresh could be in order. There’s certainly a lot of  technical minutiae when it comes to different types of men’s dress shoes . From the functional roots of wingtip brogues (the brogue detailing was meant to provide breathability in the rain) to the durable nature of a dress chukka boot, there’s a lot of ground to cover (pun intended). However, we’re going to focus on the basics: Shoes that look great with everything from a suit to chinos and a blazer, and perform just as well as you’d expect. If you’ve got additions to the list or thoughts, tweet at me incessantly on Twitter or leave a comment below. Happy shopping!

#1. Allen Edmonds Liverpool Chelsea Suede Boots — $445

The versatile and refined dress boot you didn’t know you needed.

Can suede Chelsea boots serve the same purpose as classic dress shoes? They certainly can, and I’m here to tell you why. Coming from the craftsmen at Allen Edmonds — who certainly know a thing or two about handsome footwear — the suede Chelsea boot becomes something more than an of-the-moment pair of footwear.  Built on the refined 943B last, this is a pair of dress boots as crisp as any on the market, made with high-quality brown suede, Goodyear welt construction and versatile looks (I wore mine with light wash denim and a navy blazer recently, for reference).

#2. Grant Stone Long Wing in British Tan Calf — $334.95

Striking dress shoes made to break in over time — beautifully done by Grant Stone.

#3. Allen Edmonds Park Avenue Cap Toe Oxfords —  $395

It’s hard to beat classic brown leather cap toe Oxfords from Allen Edmonds.

For absolutely beautiful footwear that’s made with the utmost attention to care, look toward Allen Edmonds. The Park Avenue Cap Toe Oxford is, simply put, a heck of a dress shoe. Available in shades ranging from crisp black (suitable enough for the most formal occasions) to an intriguing navy leather, the classic shade of brown seen above is a safe bet to become your new go-to dress shoe. Minimal enough to wear with a suit and still able to work with dark blue denim and a V-neck sweater, they’re certainly worth the investment.

#4. Ankari Floruss Brogue Derby in Black — $182.98

A classic black long wing that works for business casual and ultra-formal situations.

If you’re quick on the uptake, you might notice that we hadn’t featured any black leather dress shoes to this point — that’s changing with these fine brogue derbies from Ankari Floruss.  A recent addition to the men’s E-commerce game, Ankari Floruss is the work of noted menswear bloggers Moti Ankari and Marcel Floruss. Give them both a follow — these are some stylish fellas who know how to put together an outfit. And  they can do footwear, too — with the Brogue Derby, you’re getting style that’s sharp as a razor and ready to be worn with your favorite navy or charcoal suit.

#5. Sebago Heritage Tassel Loafers — $115

A prep staple that can be dressed up in the warmer months? Not too good to be true.

A chukka boot that can be dressed up or down.