Style is personal, very much connected to your lifestyle and personality. Which is why, even though we have some posts on how to build a starting wardrobe, and suggestions for how to dress for the office, we often shy away from listing things as “essentials.” In a recent Vogue article, it was revealed that Prince had 3,000 pairs of bespoke shoes (3,000!!) — all in one style, glamorous four-inch heels, each custom made to fit his glam-god ensembles. You’ll probably never find high heels listed as a menswear essential, but also no one more stylish than Prince.

That said, I’ve found I often reach of the same types of shoes everyday, and I’d like to think my lifestyle is a teensy–weensy more relatable than Prince’s. And in my time reading menswear blogs and forums, it seems many guys find these same styles useful too. I wouldn’t say they’re essentials — the best essentials, again, are found through trial-and-error. However, if you’re just building a wardrobe, here are five styles that have worked for me. Maybe they’ll also work for you.

A Pair of Proper Dress Shoes: Norwegian Split Toes

The only real wardrobe essential we stand by is a sincere suit, which also means you need its accouterments: a white dress shirt, dark silk tie, and a pair of proper dress shoes. Unless you wear a suit every day, however, you probably want to make those dress shoes derbies. Oxfords are too formal for sport coats and trousers — even worse with jeans. Derbies, on the other hand, span the gamut. They can be worn with tweeds and flannels; denim and knitwear; and (most) suits and ties. They don’t look as sexy, but I find them infinitely more practical.

When it comes to derbies, none make my heart pitter patter as much as the Norwegian split toe. It’s true they can look a bit taxidermic. And if done poorly, an elongated toe seam can even seem phallic. When everything comes together well, however, nothing looks as good to me. Wingtips are too common; cap toes too plain. Norwegian split toes plant your feet in the ground and say you like something a little different.

Style enthusiasts often consider Edward Green’s Dover to be the Platonic ideal, but it’s tremendously expensive. If you have this kind of money to spend, John Lobb’s Harlyn is also terrific. Both have those handsewn piecrust aprons and subtle toe seams that I think make this style look its best.

For something more affordable, check into Alden, Carmina, and Crockett & Jones. The last one has a slightly sportier style called the Durham, which rides the line between tailored clothing and casualwear, making it a bit more versatile. Enzo Bonafe and Vass offer handwelted split toes; Meermin and Carlos Santos are solid budget-friendly options; and Paraboot’s Avignon is good if you want something distinctly casual (too informal for suits, but a solid choice with denim).

Something Smart Casual: Penny Loafers

The penny loafer was the sine qua non of the post-war Ivy Look. Often worn with Shetland sweaters, flat front chinos, and tweed sport coats, they were the choice of Ivy League students across the East Coast, later finding broader appeal through Esquire. More than being an Ivy shoe, however, penny loafers embody the kind of casual, dressed-down style that the US has always championed (much like button-down collars, in that sense). In fact, that’s what originally made them popular with students, who wanted something comfortable and smart, but sufficiently casual to avoid looking corporate.

Which is why they continue to be so great today. They’re dressier than sneakers, but not as formal as lace-up dress shoes. They go just as well with jeans and casual jackets as they do with sport coats and trousers. The Prince of Wales even wears them with casual suits (although I don’t recommend them with true business clothes). I wear mine three seasons out of the year, all but the coldest of days.

Note, loafers come in a distinct range of formalities. Rancourt, Quoddy, and Oak Street Bootmakers, for example, have rounder toe boxes, making them easier to wear with jeans, and aprons made with functional moccasin stitching. The design derives from the old Norwegian and American Weejun method of making loafers: two pieces of leather form the uppers (one for the plug and the other for the sides). They’re then conjoined using a handsewn saddle stitch. If worn hard enough, that stitching will loosen up a little. Back in the day, students used to duct tape their penny loafers as they were falling apart, which for some was a mark of pride.

Compare those against the more urbane loafers from Edward Green, Carlos Santos, Meermin, and Carmina. Their toes are sleek and shapely; the apron is smoother and more refined. These can look more harmonious with casual suits and sport coats, but they can be too dressy for jeans or shorts. For something between these two worlds, try Alden, JM Weston, and certain loafers from Crockett & Jones (particularly the Boston and Harvard models). Those ride the line well between casual and formal, allowing you to switch between tailoring and jeans more easily.

The Do It All: Textured Chukkas

No footwear style can do everything for you, but I find chukkas come close. They’re an ankle-height boot that takes its name from a period of play in polo (although, like a lot of menswear history, stories are often mythical and muddled, and there’s little evidence chukkas were actually worn for polo matches). Still, depending on their details, I find they go with nearly everything — casual suits, leather jackets, raw denim, casual trousers, and even fatigues. They straddle the line well in terms of formality.

I like chukkas in a textured brown leather, such as a suede or pebble grain, which I find helps visually break up the vast expanse of material that stretches across the vamp and instep. If you get them with a studded Dainite rubber sole, they also work pretty well as rainboots (just treat the suede uppers with a weatherproof spray and give pebble grains a quick brush down with a wax polish).

Unlike with split toes and penny loafers, there are often fewer details here to get wrong, which is good news if you’re shopping on a budget. Affordable chukkas from Loake, Herring, and Meermin can look just as nice as higher-end options from Alden, Allen Edmonds, Enzo Bonafe, and Vass (although Enzo Bonafe and Vass, being handwelted, are better built). Mine, pictured above, are Crockett & Jones’ Brecon. Many of the usual suspects also have terrific chukkas — Zonkey, Saint Crispins, Alfred Sargent, Edward Green, and Carmina. Unlined models can feel extra comfy in hot weather, but they’ll lack the structure you may want for winter.

For Real Casualwear: Simple, Mostly White Sneakers

It’s good to have a pair of authentically casual shoes, especially if you wear chinos or jeans. Typically this means sneakers — usually white, often simple. Sneakers can help an outfit feel a bit more relaxed and natural. You can even use them to dress down casual sport coats and tailored topcoats, although I find they still often look better with jeans than trousers.

Some of my favorite sneakers these days include Vans slip-ons and Margiela’s German Army Trainers. Plain white sneakers, a la Common Projects, are nice but also a bit ubiquitous. Vans and GATs, on the other hand, have that casual feel that can feel better with sportier, relaxed clothes. I wear mine with camp collar shirts and jeans in the summer, or leather jackets come fall. Adidas also has their version of GATs at the moment, and they’re a lot more affordable than Margiela’s.

Retro-style runners can also be great if you like “Rugged Ivy,” a term for that period in the 1970s when Americans repurposed outdoor brands such as Sierra Designs and Eddie Bauer into their everyday attire. Think: 60/ 40 parkas, Levi’s jeans, and Champion sweatshirts. I especially like Spalwart’s Marathon Lows for this sort of thing, but there are a ton of other options. Other solid sneakers include Chuck Taylors (I like the cushier 1970s version); Nike Air Force 1s (Common Projects and Vor are great upscale-versions of the same design); and Adidas’ Stan Smiths. Check our sneakers tag for more suggestions.

Your Experimental Pair: Side Zip Boots

Finally, make your fifth pair personal, buy something unique. By experimenting with new things, you may find your wardrobe grows in unexpected directions — a pair of pants to go with some new shoes, then a jacket that you didn’t think you’d ever wear.

My wardrobe has really grown in the last few years through my wearing of side-zips, which are close cousin of Chelseas and ropers. They’re a slightly taller boot, usually six inches in height, and have a zipper on the medial part of the foot. Some are clean enough to go with minimalist styles such as those from Lemaire (one of my favorite designers at the moment); others are a bit more rugged and sit better with workwear.

I love Margiela’s zip boots for their silhouette. Over the years, they’ve made sleeker designs and a chunkier, slightly square toe they call their Campus. As it often goes with designer shoes, however, the quality leaves a lot to be desired. The leathers are often thin and treated; the soles glued on. Buying them in suede helps, but guys who are sticklers for quality may be left feeling cold.

If quality is important to you, check out Buttero and Viberg. Buttero has lightweight, Blake stitched boots that work across a range of casualwear styles. Vibergs are a bit more rugged, but still reasonably versatile. Division Road has them in a beautifully rich Horween leather, Lampo zippers, and a Ridgeway sole with dropped midsole to keep them relatively elegant. Sizes are mostly sold out, but they’ll restock soon (the boots picture above are the same boots, but aged).

Lucchese is also a nice, slightly sleeker design. Just buy them in suede, as the smoother calfs can look artificial. TWLV seems good, although I wish they didn’t burnish those toe boxes. Kapital makes some of my favorites, but they’re hard to find outside of Japan (those are dyed with a fermented pomegranate juice that helps the uppers take on a unique color as they age). Lastly, Husbands Paris looks interesting if you like a more mid-century Mod look.