For most guys, their first footwear purchase is a pair of sneakers. And that makes sense. Sneakers are comfy, versatile and relatively affordable. But when it comes time to extend your shoe collection, the options can be daunting. Chelsea boots? Chukka boots? Desert boots? Slip-on shoes? Lace-ups? Full leather or suede? And we haven’t even started on colour yet…
In this article, we’re going to break down three shoe types you should add to your casual wardrobe, once you’ve got the obligatory white leather sneakers out of the way.
Every guy needs a good quality pair of Chelseas in the wardrobe. These are arguably the most versatile men’s shoe on the market. You can wear them with a suit, jeans or chinos. Style them up or down. They come in suede and full leather. And they’re ridiculously comfy to boot.
We’ve gone into more depth on Chelsea boots in the past, but essentially they’re close-fitting, ankle-height boots with an elastic side gusset. No laces. They originated in the 1800s and come in high and low profile varieties. If you’re just getting started with Chelseas, pick something flexile, like a brown leather DEXTER or LUCCA. You can wear these with jeans and a flannel shirt, or tan chinos and a caramel bomber. Frankly, it’s very hard to make Chelsea boots look bad.
Next, get yourself a pair of Chukka boots. Originally known as Clarks Desert Boots, Chukkas are mid-height ankle boots with rounded toes, two or three eyelets and a two-part leather upper. They’re generally considered slightly more casual than Chelseas.
We’ve written a comprehensive style guide for Chukkas, but again, it’s hard to go wrong here. Just grab some indigo denim, throw it over a pair of BRODY or LANARK Chukka boots, then layer up with a crew tee, simple knit, and a khaki utility jacket. That look will take you almost anywhere. Leather Chukka boots work great with texture, too. Try them with woollen pants and a denim shirt, or cuffed chinos and a woolly peacoat.
The quickest way to elevate your casual game? Branch out from the basics. There’s nothing wrong with starting with a pair of white leather DECO 2.0 sneakers, but there are literally dozens of other sneaker styles to explore: high-tops, slip-ons, smart-casual, athleisure, skater canvas, textile blends, ironic dad sneakers. The sky’s the limit.
To expand your sneaker collection, try mixing up materials. If you already have a full leather pair, try some RUDY sneakers in olive suede, or DECO 2.0 in grey nubuck. These look great with invisible socks, cuffed black jeans and a chambray shirt. The trick with sneakers is keeping them clean: even the best leather sneakers can degrade without care, and nothing cheapens a great outfit like ratty, mud-covered sneakers. Check out our sneaker cleaning guide to keep your kicks looking their best.
So you’ve got one or two pairs of sneakers, Chelsea boots and Chukka boots. Your collection is looking pretty good. But there’s one area missing: slip-on casual shoes. These are great during the warmer months, when you can quickly through them under some high-cuffed chinos, or even a pair of shorts. For a crash course in slip-ons, check out our dedicated styling guide.
It’s hard to narrow down the slip-on category to a single shoe, but if you have to pick one style, go for a driving shoe. Something like the BALFORT 2.0 is a great choice. You can wear these under tailored pants or chinos. Just match with invisible SETH socks, navy pants, and a crisp linen shirt. That’s a great outfit for wineries, roadtrip, summer lunches or even a weekend footy match.
The Golden Rule
The main thing to keep in mind when building a shoe collection is versatility. You want shoes that straddle a few social occasions, or can be styled up and down. This will extend the wearability of your shoes, and give you better value for money. All of the shoes listed above fall into this category. When you’ve built out the basics, feel free to splash out with different materials (like suede and nubuck), and more exotic styles like monk straps and espadrilles.
How many shoes is too many shoes? That’s something every guy needs to decide for himself. Most of the time it’ll come down to budget, space and your partner’s patience.