After a bit of consideration, I decided that flannel with sneakers of any color is perfectly “okay.” You need to watch out for how you pair your shirt and shoe colors, however. The type of pants you wear also matters, and you can gain some inspiration from how two celebrities, in particular, wear flannels with black sneakers.
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1. With Faded Jeans and Brown Sneakers
I’m starting you off with what I perceive as a rather “ordinary” outfit – no offense to the men out there wearing similar. It’s a “safe” choice for which a man would not experience much ridicule at the park with his children or at outdoor events.
This outfit works for just about any casual occasion, including the middle-aged version of “clubbing” or hiking and camping. It’s also an excellent way for a man to dress if he wants to appear as neat as possible even if working as a mechanic, welder, construction worker, or other “hands-on” profession.
2. With White Sneakers
White golf or tennis sneakers made of leather or canvas work well for the “smart casual” dress code that rates as more than casual but less than formal. This style of dress calls for neutral plaid colors, such as navy blue or brown with white or dark red accent shades. In this case, the flannel would often pair with khaki or other non-denim pants.
Subtle striped or solid colored flannel also helps you pull off this neat and trendy but relaxed style. However, compose your outfit wisely when dressing this way. Taylah Brewer of The Trendspotter suggests says that you should “ensure that your flannel is a good fit and not too baggy.”
3. With Skinny Pants (Both Jeans and Non-Denim Fabrics)
Snug-fitting and straight-leg skinny jeans come more than in the traditional faded blue. You’ll also find them in red, black, brown, white and black for the denim and the leather, suede, vinyl, cotton or synthetic fabrics. The blue or black skinny jeans paired with the flannel will probably present itself to you more often than other skinny pants and flannel ensembles, however.
Combined with just about any color sneaker you want, you can wear skinny jeans with any plaid print. You can even mix and match them with striped or solid flannel shirts. However, the classic red and black checkered flannel never “gets old,” and always pairs well with all-black underneath it.
Elsewhere, on social media and in the news, skinny jeans with different styles of black sneakers have risen in popularity. Two celebrities, in particular, show you how it’s done with either black sneakers or high-tops. Check out what Travis Scott and Kanye West have done with their flannels from about 2015-present.
4. Travis Scott’s Flannel and Black Sneakers Outfit
Photographers caught Travis Scott in the trendy NoHo New York neighborhood wearing this flannel outfit on September 13, 2016. For him, he probably considered it just another day that for some picture takers turned into the prime “celebrity candid” opportunity. Notice the contrasting colors of the plaid and the coordinating jeans.
You could argue that the black sneakers in this outfit don’t offer as much value as the red and black Nikes Travis Scott wore at least once with a black and white flannel shirt that had hints of red in it. However, the sneakers he wore in December 2016 with the blue and orange plaid do at least have some texture on the sides. For just casually walking around in NYC, his NoHo outfit’s not the worse looking combo.
5. Kanye West’s Flannel With Black High-Tops Outfit
On December 19, 2015, photographers saw Kanye West holiday shopping on Rodeo Drive in Beverly Hills. It’s not uncommon for celebrities to wear one color underneath and accent the top layer with hints of color. He appears to cater to his own comfort rather than worrying about style at that moment. However, he seems to have made history just by complimenting an otherwise plain, solid black outfit with a touch of the green plaid print.
I speculate that either Kanye or his fans enjoy him wearing green because he did it again about a year later. On August 6, 2016, picture takers spotted Kanye West leaving “The Nice Guy” lounge in Los Angeles. The zipped green flannel has a similar shade of green in it that the button-down shirt did in the first instance of Kanye wearing green flannel with black.
The shoes have a slight brown tint to them, however, which matches the T-shirt he’s wearing underneath. The pants color appear to be a bit lighter than the skinny jeans he wore a year earlier. This look apparently caught on because Gentlemen Quarterly had documented both times when he wore this similar color combination with a green flannel as the overlay. It became a part of the Kanye West “Look Book.”
To Flannel or Not Flannel With Sneakers?
I noticed several instances of the plaid flannel shirt layered over a T-shirt when wearing it with sneakers. It’s probably one of the most common ways to wear this print either combining the plaid flannel with hiking or cowboy boots. I think that works, especially if worn with skinny jeans for either casual or “smart casual” occasions but not for formal use.