Men’s Dress Boots: The Complete Guide

Men’s dress boots are an absolute wardrobe staple. You can wear men’s dress boots with jeans or a suit, depending on the style. They are the perfect mix of rugged everyday utility and smart style.

The first step in choosing men’s dress boots is material and style. They can come as casual as suede or as formal as patent leather, with a price tag to match. As for style, dress boots have a long history and so have developed a wide array of styles from the chelsea boot to biker boots.

Chelsea Boots

Men's dress boots loake chelsea boots
Loake Chelsea Boots

These men’s dress boots derive from traditional riding boots. Because of this they have elasticated sides around the ankle. This is ideal for today’s world as you can slip them on instantly and yet still look great.

The secret to buying the best chelsea boots is to get a good fit around the ankle, otherwise you look like you’re standing in buckets. A snug fit on the other hand reveals your lower leg smoothly conforming to a beautiful leather shoe. This hardly matters when you’re standing but as soon as you sit down the top of the chelsea boots becomes much more relevant. See our list of top chelsea boots here.

If you are being especially daring you can get chelsea boots with coloured elastic accents. Chelsea boots themselves come in a wide range of colours.

How to wear chelsea boots

The great thing about chelsea boots is they go with just about everything. They add a smart touch to a pair of jeans but equally look great with a suit. For most uses a pair of black chelsea boots is all you need, although brown leather or suede is great for more casual looks. High quality designs come with a hand stitched leather sole which looks the best – although you may want to have a cobbler add rubber on top for extra grip and to last longer. Alternatively, plenty of brands offer a rubber sole which may not be as elegant but offers great durability for everyday use.

Lace up dress boots

Allen Edmonds Men's Dalton Lace-Up Boot
Allen Edmonds Men’s Dalton Lace-Up Boot

These classic boots have barely changed in over 100 years. Lace up ankle boots come in a range of styles from plain military style boots to brogue boots with decorative toes. These come in a huge range from very cheap to premium luxury. They can take a while to break in so be careful that the ankle doesn’t damage your calf. Some come with padding at the back to prevent this. Many brands tend to offer these with a very chunky sole but for mens dress boots  try and find a leather or slim rubber sole.

Chukka Boots

Rockport Men's Classic Break Chukka Boot
Rockport Men’s Classic Break Chukka Boot

While these don’t really qualify as men’s dress boots, the mods of the 1960s wore these suede boots with their italian suits and the look continues to be popular today. While the classic tan suede boot is the most common, chukka boots tend to come in a wide range of colours and materials. We would recommend pairing these with more of a youthful  prom suit – a slim fit in an exotic colour – rather than trying to combine them with a business suit. As casual suede boots they work great with a pair of jeans and are comfortable enough to replace a lot of the times you would normally wear trainers. 

Side zip dress boots

Stacy Adams Men's Santos Plain-Toe Side Zipper Boot
Stacy Adams Men’s Santos Plain-Toe Side Zipper Boot

This style of boots is somewhat of a hybrid between biker, cowboy and chelsea boots. It’s amazing shape is provided by the side zip which means it can hug tight like a chelsea boot but doesn’t need the elastic – and so you only have shiny leather instead. They are frequently combined with a cuban heel that makes them incredibly good looking, although often not so comfortable and easy to walk in. You should also watch out for the toes as these tend to be quite pointy which can lead to discomfort and damage.

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