The men's slip-on "Chelsea" ankle boot (and similar buckled "Jodhpur" boot) are the rage right now. They're the perfect balance between casual and dressed-up and can be worn with just about anything from jeans to a suit*.

Crosby Square "Keating" Jodhpur Boot $375

A pair of smart boots will take you from the office on Friday straight through to Sunday brunch all winter long (and several winters to come) if chosen well.

Generally, you're looking for the following:

quality leather or suede upper
slightly narrow round toe (not square)
rubber sole - if you walk
leather sole - if you drive
subtle details (if any)

By far the most popular brand of Chelsea boot is Common Projects, however, the price will shock you (in a bad way).

Truth be told, I do not recommend the rubber crepe sole of these Common Projects boots. The porous crepe inhales dirt and is near impossible to clean.

Thankfully, since the Chelsea boot is so popular right now, there are more affordable options to choose from, though, a quality pair is still a bit of an investment.

When looking for boots, the first identifiable sign of quality is whether or not the sole is stitched to the upper body instead of "cemented" or glued. Called "Blake stitching" this prevents the sole from falling apart after only a few wears. Stitching can usually be seen around the bottom of the outsole like the Crosby Square boot shows below.

Some shoe soles include an additional piece of leather, referred to as a "Goodyear welt" after the man who invented the welting machinery. The welt is visibly stitched (or "welted") in between the upper body and the sole around the entire front of the shoe. This extra reinforcement makes the boot more water resistant.

A Goodyear welt is easily visible on the below Red Wing Ranger boot for example.

Second, the quality of the leather or suede used for the upper is obviously also important since it is the most visible. If it's good leather it'll age beautifully and last forever.

Finally, an added benefit is if the inner linings are also leather, which helps the shoe breathe and reduces that inside smell.

The boot brands I list below are known for their dedication to quality, both in the materials used and the construction. And are a couple hundred dollars cheaper than Common Projects.

Best Leather-Soled Chelsea Boots Below $399:

Best for indoor use and for a more dressed-up refined look. For those NOT daily slogging outside to and from the office, choose a boot with a leather sole like the two I recommend below.

1. Grenson - English brand known for making top quality shoes in general.

Grenson "Declan" Chelsea Boot $320 (SALE) — Grenson "Declan" Chelsea Boot $320 (SALE)

2. Crosby Square - makes a great Chelsea boot out of Spain (though the same cannot be said about their regular shoes made in Italy).

Crosby Square "Kensington" Chelsea Boot $365

Best Rubber-Soled Chelsea Boots Below $399:

For those who daily walk outside to get around town, choose a rubber-soled boot. While more durable, below styles are still very handsome.

1. Magnanni - well-made boots.

2. Frye - long-standing excellent boot brand.

Best "Weather" Chelsea Boots:

For those that slosh through particularly rainy or snowy winters, you can do it in style.

1. Sebago - not officially "weather" boots, but they're pretty resistant to the elements.

2. Hunter - iconic British waterproof boot brand.

Enjoy the winter (as much as one can)! These boots should help.

*To wear with suits: select leather instead of suede. Jodhpur boots that have a buckle instead of elastic-featured Chelsea boots may be a better choice.

Best Value in Chelsea Boots

Best Leather-Soled Chelsea Boots Below $399:

Best Rubber-Soled Chelsea Boots Below $399:

Best "Weather" Chelsea Boots:

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