How to Wear Boots in the Summer 🌤️

Be the BEST dressed in town.


Absolutely. But if I had to guess, you’re probably traumatized by the disrespectful amount of heat and ungodly amount of sweat that will follow (Yes, it’s a packaged deal). Totally understandable. But if you’re looking to have a well-rounded style and closet, then a pair of solid boots is a must have. Sneakers aren’t quite fitting for every occasion or sometimes don’t do the fit justice. Loafers on the other hand, are always a great option, but if I had to guess you’d like to avoid being a one trick pony.

And this my friend, is exactly why I’m such a huge fan of boots. They seem to be the silver bullet to that problem that eventually plagues us all…‘not having anything to wear’. There’s arguably no place a solid pair of boots can’t take you, from a dinner date, a trip to your favorite bar or lounge, or a simple errand run around town. I’ve put together 3 different ways to style your boots this summer, while of course preserving a good deal of comfort.

1. The Trouser Approach

If you aren’t up on game just yet, trading in your durable but heavier denim for a pair of trousers, is a major summer style hack, especially if you don’t plan on doing a bunch of rigorous movement, or work related activities. Any style of ‘leather’ boot will work, but for this occasion, the goal is to stick to a sleek sophisticated approach at the bottom, hence the combination of our Damien Chelsea Boots, and Dark Brown Plaid trouser. Both items paired together, provide a solid foundation of sophistication & class…and allow you to take the remainder of the fit wherever you’d like. For instance a simple t-shirt would work just fine, as long as it’s tucked in, or you could even take things up a notch by layering with a summer jacket.

I stuck to the middle ground on this one, with a pairing of our Aztec Print Camp Collar shirt. Not too dressy, not too casual, and most of all, breezy addition for those summer evenings. To add a hint of that retro vintage feel, I had our tailor alter the Trousers with a slight boot cut. This is actually much simpler than it sounds, and if you don’t already own a pair of boot cut trousers, all you have to do is find a slim to straight cut pair of trousers.

Keep the leg opening ‘as is’, and slim down the fabric at the thigh, taper the knee and upper calf area. And that’s it. Whenever the evening calls for an upscale restaurant or lounge, this combo is one of my favorite go to’s.

2. The Fedora + Vest Combo

So what if you are in the mood for a rugged vibe? Then you’ll need a pair of boots with a little more attitude. Specifically, a lug sole boot, which typically features a thicker rubber sole and aggressive teething to stand your ground…think the ferocious appearance of a decked out Ford Raptor 🚜. This style of boot is designed for utility, featuring the standard construction of a work boot, so it naturally gives off a super masculine and grungy vibe. And nothing beats adding a dose of sophistication to that mix, and to do just that, it all comes down to the right layers and accessories.

A vest will do the trick here, especially with a pairing of a slim fit solid-colored tee. Finish things off with a classy brim, newsboy cap, or a vintage or signature ball cap. For this look, I had every intention of our Preston boots doing the heavy lifting, hence the Honey color choice and understated neutral Grey Trilby Fedora. For an evening hang at a more casual bar, or night out with the fellas, I think you’d agree that this is a staple uniform that’s completely riddled with swagger. And so if you ever find yourself struggling with a fit, just lace up then vest up!

3. The Cargo Edit.

There’s levels to errand runs. Maybe you’re doing some shopping at the Galleria or at your favorite stores, mailing off packages, a service appointment at the dealership, or whatever it is life throws your way. And if you’re in your 30’s like myself, beyond or approaching it…then a pair of shorts and Jordan 1’s just doesn’t cut it. Even when handling the simplest of activities, more times than not, you’re treated and serviced in the manner you appear. This my guy, are the sad realities of life. But the good news is style is our secret weapon. Now we aren’t aiming to look super-duper fly. So, the goal here is to stay relaxed yet put together…effortlessly might I add.

Two words….Cargos & Chelseas. Crepe soles to be exact. If you are yet to own a pair of crepe soled shoes or boots, just know whatever comfort it is you love and cling on to with sneakers, well you’ll get them in these. And hey denim is great, but with an outfit this simple, a good way to spice things up is with some statement pockets. (Shhh our Cargo Trouser Collection drops next month 🤫).

Add a relaxed fit T-Shirt, and the right watch, and it’ll make a world of difference. If you’re reading this, I trust that you’ve already got a load of style, and more than likely have some lethal time pieces in your arsenal. But just in case you don’t… metal or leather is the move, but definitely NOT silicon. Lastly, a staple trucker or ball cap to shield you from the sun and you’re all set. And just like that, you'll portray yourself as someone who is about his business, and worthy of immediate attention…even on your day off!

Well I hope you enjoyed reading this style journal, as much as I’ve enjoyed styling and writing it. But hey I need a little help. Let me know what you’d like to see next or what style tips you’d like to learn more about, by simply replying to this email 📮, and the team and I will get right to work.

And if you’re in the market for some new boots check out our Boot collection, with our recent addition of the Preston Boots in Honey and Dark Brown. We’ve got some cool stuff that’ll add some grown man drip to your overall style. In the meantime, I’ll get back to work, and have some more cool tips delivered to your inbox next week.

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