Back To Cool: The Flyest Boots & Jacket Combinations [STYLE GUIDE]


If you were contemplating going through this fall/winter without a proper pair of boots and a jacket to match, you need to reassess your life, bruh. An essential element for stunting through the fall, the boot and jacket combo should be a well-refined element of every man’s wardrobe. Sure, others may chose to wear floppy sneakers through the rain and sludge, but that isn’t you–let them deal with the atrocity that is wet socks.

Not every pair of boots and jacket go well together. This isn’t peanut butter and jelly. You need to factor in materials, color hues, functionality and overall aesthetic appeal. But, like always, we did all that groundwork for you so you can kick back and get fly. Check out the coldest Boot and Jacket Combinations below:

1. Diamond Supply Co. GI Boot & Afends Zimbaloo Jacket

We featured an alternative color way of this boot by Diamond last week. The GI Boot does a nice job of blending luxury with ruggedness. These will hold you down through the elements and catch eyes along the way. This jacket from Afends is also perfect for these boots (PB&J?) thanks to the color accenting on the sleeves. Pair these for your go-to combination for the warmer months in the fall.

Diamond and Afends

2. SWIMS Helmut 2 Boot & Crooks and Castles Problem Solvers Jacket

SWIMS does a great job of creating an entirely waterproof boot (you won’t need these anymore) while keeping it stylish and modern. Inspired at the classic desert boot, these Helmut boots will save your life on those walks across campus in the middle of a inconvenient monsoon. Crooks never fails to create dope pieces, and this grey camo jacket is no exception. Featuring a corduroy collar to keep you cozy and five pockets to stash all your paraphernalia, this jacket has it all. Keep this combo on deck once the cold sets in after Halloween.

Crooks and SWIMS
3. Red Wing 6″ Moc Boot & Staple Composition JacketA cornerstone of American footwear, Red Wings does the classic 6″ Moc Boot very well. Just make sure to size down a half to full size when buying them as they historically run big. This Staple Jacket may be on the louder side, but the speckle cement print is a statement maker. Stay dry, warm AND fly at the same time. We make it look easy, don’t we?


4. Eastland 1955 Baxter Boot & Rothco M-65 Field Jacket

This Eastland x Rothco combination has a military feel to it, but it’s only fitting. If you’re going to prepare to battle the elements, you might as well do it at the highest level possible. Everyone should have a field jacket in their wardrobe, and Rothco does it the best at a great price point. Get ready to hit the streets in style.

Eastland and Rothco

In case you were searching for what to wear under your new jacket, we got you covered with our Cozy Crewnecks recommendations: HERE

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