A Quick Guide for Men on Wearing Boots with Jeans

November 1, 2012 • By Robert

Fall is here and winter will soon be on its way. If you haven’t already, it’s now time to break out your boot collection. It may even be time to go out and buy that new pair you have your eye on.

On a separate note, I think it’s safe to say that most of the world’s population wear jeans on a regular basis. Many of us even have a few pairs we like to use in rotation. For this, we couldn’t think of a better time to put it all together and discuss how to properly wear boots with your jeans.

Let’s put it out there now and quickly discuss the jeans. We are in modern times, so let’s stay with a modern cut! Stick with a pair of fitted denims, tapered leg or skinny fit if you prefer. The boots will dictate what jeans you wear and how they should be worn.

There is no blueprint nor any strict guideline that must be followed when it comes to pairing these two items. We did, however, put together some sensible tips that can make you look put together in those pieces. But before we list some of our pointers, let’s see how some of today’s hottest celebrities are wearing them.

Adam Levine displays his rock edge by wearing a pair of medium-wash denim jeans and black derby boots.

Adam Levine, frontman for pop group Maroon 5, arrives at the Ed Sullivan Theater for his appearance on the Late Show with David Letterman, New York City, October 25, 2012

No one does trendy, grunge better than Jared Leto. Check him out in his dark denims and combat boots:

Actor/singer Jared Leto spotted at the 2012 Coachella Valley Music and Arts Festival in Indio, California, April 13, 2012

Now, let’s go through some stylish boot choices and how they can be nicely paired with jeans.

1. Workwear Boots

Red Wing 1907 Heritage Classic Lifestyle, $249.99; J Brand Tyler Jeans, $218.00

This pair plays right into the all-American workwear look. With its rugged and masculine appeal, it would be best matched with distressed medium- or light-wash jeans. Some may disagree, but don’t be afraid to tuck your jeans in. It doesn’t work with just any boots, but it does with workwear boots.

2. Chukka Boots
Endless Two-Tone Lace Chukka, $475.00; Dolce & Gabbana Skinny Jeans, $215.00

Chukka boots are versatile. They are casual but with a slight hint of formality. With that said, medium- or dark-wash jeans could work perfectly with this style of boots. I would heavily advise to fight the urge to tuck your jeans into the boots as they are not a rugged looking type of footwear. To avoid messy scrunching at the bottom, try neatly folding the bottom of your jeans to ankle length; it helps show the clean, trendy look of the boots.

3. Chelsea Boots

Barneys New York Plain Toe Chelsea Boots, $435.00; Cheap Monday Tight, $75.00

With its old English charm, this type of boots looks great with semiformal wear or a smart casual type of outfit. In choosing denims, go with the dark-wash type with a clean bottom hem. We are going for a sophisticated look here.

4. Brogue Boots

Mark McNairy New Amsterdam Brogue Boots, $480.00; Ksubi Chitch Slim, $290.00

The brogue is a very unique type of footwear as it is the easiest to pair with either formal or casual wear. Formal looks good with the boots’ intricate perforations, but casual matches the footwear’s sturdy leather construction. In my opinion, this is the only type of boots that looks great with your jeans either tucked in or placed outside the boots.

5. Combat Boots

Marc by Marc Jacobs Short Combat Boots, $450.00; Neuw Lou Slim Jeans, $199.00

Combat boots are by no means subtle in appearance; they actually deserve a full feature. Worn similarly to the work boots, choose light, distressed jeans, and make sure to tuck them in. Let the boots be the star of your outfit.

6. Derby Boots

Officine Creative Hidden Stitch Derby Boots, $695.00; AG Adriano Goldschmied The Protege, $172.00

Typical derby boots are similar in style to the Chelsea boots in that they both feature clean lines and are both fairly simple in design. The major difference is that the derby has laces. When pairing them with denim, look for a dark-wash pair with a clean hem for a sophisticated look.

7. Moto Boots

Balmain Plain Toe Moto Boots, $1,260.00; 7 For All Mankind The Slimmy, $218.00

Moto boots are a common subject of debates in terms of how to wear them with jeans. While there is no definitive right or wrong answer, my position is to stay away from tucking your denims in. Typical moto boots are mid-calf in length, which I feel is much too high for a tuck job. Keep the look fairly clean by reaching for either medium- or dark-wash jeans. As for the bottom, going with a clean hem or a crisp fold is a sure thing.

Credit: Kyle Blair/WENN.com/STS