putthison:

Q and Answer: Ten In-Between Shoes

Matt asks: I need a new pair of shoes!  What I have right now is either too casual (a sneaker) or too formal (a fancy dress shoe), but I’m trying to figure out something in between. Any suggestions?

This is a question we get a lot. For men who want to wear something a little more put-together than their beat-up Nikes, but aren’t yet ready for a full-on sportcoat-trousers-dress-shoes ensemble, is there anything in between?

The simple answer is: yes. Here are ten choices for casual footwear that will keep you a head above the dirty sneaker crowd. (It’s a little tougher in the summer, so I’ll start there - the pictures run left to right and top to bottom.)

1. Refined sneakers. When choosing sneakers, look for simplicity. White’s a great color for spring and summer, black and brown will do you well in the cooler months. You want as few details as possible here, and if you’re going to try and dress them up, they should be clean and sharp. I’ve got some Common Projects, the gold standard for this kind of thing, pictured above, but if you can find similarly simple leather sneakers from a brand that doesn’t cost a bajillion dollars, go for it.
2. Boat shoes. While their ubiquity the past few years or their inherent preppiness might be a turn-off, boat shoes remain the default casual summer shoe (non-sneaker category). Wear them without socks in pretty much any casual situation during the hot-weather months. Then put them away.
3. Espadrilles. These are the classic European vacation shoe - what Cary Grant might wear to the French Riviera. They’re cheap, comfortable and refined. Just don’t try to wear them outside of summer vacation, and for goodness’ sake don’t wear those awful Toms.
4. Crepe-soled Chukkas. Desert boots are a comfortable, good-looking mostly-casual shoe for nine months of the year. Like boat shoes, they’re starting to overwhelm with their ubiquity, but if you try an alternative style like the calf version above, you can get a little more refinement and a little less “been there, done that.” (I can’t believe I just typed “been there, done that.”)
5. Leather-soled Chukkas. Chukkas with leather or dainite soles like the brown suede pair above are one of the most versatile shoes you can own. They’re great with jeans, and in a pinch they could even be worn with a suit (though maybe not in suede). 
6. Camp Mocs. Camp mocs are the cool-weather equivalent of the boat shoe. Inexpensive, casual, preppy and a little more refined than sneakers. The LL Bean Blucher Moc is the standard here, though the quality isn’t as high on them as it once was. Works great with jeans or chinos, but not so much with a more formal look.
7. Plain-Toe Bluchers. This is the classic casual shoe. My own pair is an old double-soled pair of Florsheims in shell cordovan. I wear them with everything short of a suit. Black looks like security guard shoes, so avoid it. Brown is a touch more casual than burgundy, and crepe soles a touch more casual than leather.
8. Country Brogues. Grenson is the classic maker of real country brogues, so that’s what you see above. The leather in shoes was originally perforated by folks who lived in marshy, wet conditions and wanted shoes that shed water. It’s purely decorative now, but still casual relative to other oxfords. If you want to wear brogues casually, look for prominent broguing, a stout shape and heavy soles. These are too casual for most suits (save country suits like corduroy or tweed), but if they’re clunky enough, they can stand up to blue jeans well. The boot equivalent of these shoes is even more casual. Note, also, that crepe soles or (especially) suede can turn down the formality of most dress shoes.
9. Work and Outdoor Boots. There are a broad range of work-style boots. I’ve pictured something in the middle, the Red Wing Gentleman Traveler. On the casual end are hunting and hiking boots (like Danners) and real work boots (like traditional Red Wings, with lug soles and moc toes). I love my Alden Indy Boots, which are moc-toed, but otherwise quite refined - I wear them with chinos or jeans and a casual blazer all the time. Also in this category are military-inspired boots, like Polo Rangers.
10. The Chelsea Boot. I’ve pictured a pair by the Australian maker R.M. Williams. A hefty, chunky Chelsea like these is more casual. A more refined model can even be worn with a suit. In fact, the Chelsea is probably the shoe that most comfortably goes from casual to formal.

Remember: city is more formal than country. Leather soles more formal than rubber (and lug soles the least formal of all). Smooth leather is more formal than textured, which is more formal than suede, which in turn is more formal than unpolished. Shoes are more formal than boots. Shapely is more formal than clunky.

And always, always stay away from hybrids. Nothing good can come of two shoes mating.

Finding a level of formality that’s between slovenliness and traditional business dress is vital for anyone who isn’t a slob or a traditional businessman. Hopefully this will set you on your way.