Tucking Pant Legs Into Boots: Ever Okay?

First in an ongoing series in which the staff of Gilt MAN debates current topics in men’s style with an intensity that is—we'll be the first to admit—a little out of proportion to the actual significance of the issue at hand.
Photo: Getty Images

Rag & Bone, Fall 2008: An argument for the look.

On Dec 8, 2010, at 9:42 AM, Andy Comer wrote:
My two cents: Sure, if you’re shoveling snow or fly-fishing in the Beaver Kill. In other words, if there’s a practical, functional reason to do so. But as a pure style move… Unless you’re a member of Einsturzende Neubauten, not something I’m a big fan of.

On Dec 8, 2010, at 11:00 AM, Jared Flint wrote:
I think a lot of it has to do with the transition a lot of guys are making from sneakers to boots. A ton of guys who used to sport Dunks and Jordans have opted for Wolverines and Red Wings but haven’t fully let go of that sneaker swag. There’s absolutely no functionality to it in the West Village. You end up looking like Jerry Seinfeld when he wore cowboy boots… and he didn’t want to be a cowboy. It looks like your ankles are suffocating. If your pants have been effortlessly caught on a boot fringe, so be it… otherwise, a bit precious/contrived.

On Dec 8, 2010, at 11:21 AM, Andy Comer wrote:
(Tyler furtively untucks.)

On Dec 8, 2010, at 12:21 PM, Tyler Thoreson wrote:
I must say, for two guys with such admirable personal style you’re coming off a little curmudgeonly on this topic. I’d think twice—and maybe look in the mirror—before making the argument that practicality is the only justification for adopting this look or any other. I mean, couldn’t you use the same argument against any number of wardrobe-enhancement techniques each of you regularly employ, from pocket squares to neckties to cuffed jeans (really so different from tucked-in?)? None of those have any real practical function, either.

What say you to that?

On Dec 8, 2010, at 1:32 PM, Andy Comer wrote:
I’m the last person in the world who would uphold practicality as an absolute. (I’m much more into frivolity! Oh, and for the record I’m an unrepentant curmudgeon, too.) But one principle I will trouble myself to stand up for: aesthetics. And the tucked-in boot thing just doesn’t look right to me. (Again, unless you’re a fly-fisherman or a member of an early-’80s industrial rock band. Or Santa Claus. I love Santa Claus.)

On Dec 8, 2010, at 2:39 PM, Jared Flint wrote:
I never think twice and don’t even own a mirror. That’s not true at all. None of us escape vanity and the sweet spot for guys is fussing about just enough in the mirror (hopefully without anyone seeing) until you’ve tucked and pulled your way to looking like you didn’t give a second thought to how you look… but look great all the same. I think I just don’t enjoy that silhouette right now, at this exact moment in time. Then again, there’s some ugly crap in my closet. Also, Santa Claus always freaked me out. Isn’t he just an over-the-hill cat burglar? He’s the Kenny Powers of home invasion.

On Dec 8, 2010, at 4:34 PM, Tyler Thoreson wrote:
Setting aside your feelings about Santa Claus, who I always imagine to have a filet of smoked salmon in his pocket courtesy of Dan Aykroyd’s memorable turn in red fur in Trading Places, I think we are in agreement. Which is to say: a) fuss and preen all you like but never to obvious affect and never in public, and b) pants tucked into boots isn’t objectively wrong, just subjectively not so right. HOWEVER… I remember being intrigued by the way stylist Natasha Royt wrapped the bottoms of the suit trousers in Rag & Bone’s Fall ’08 runway show with what looked like nineteenth-century ankle weights. (Not that I know what nineteenth-century ankle weights actually look like.) That technique might come off as a little affected for for real-world wear, but it did a nice job of revealing the badass Northampton boots on David Neville and Marcus Wainwright’s models. Of course, it’s also worth nothing that she’s a professional stylist and you (and by you I mean me) are not.


Ed. Note: We just noticed our colleague Mordechai Rubinstein weighing in on this very topic, via Twitter…

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  2. Nate says:

    I tuck my jeans and my pants into my boots frequently but since my boots are not as tight in the ankle/calf as the picture it is almost a completely different look. I rock some Frye’s, RedWings and Vintage Combat Boots I got an Army Surplus Store in Park Slope. All of them have a looser fit in the boot.

    It honestly started off as more of a practical solution when it was raining and I kept splashing water onto the legs of my pants. Now it’s intentional. Everyone’s allowed to have their own taste and opinion. That’s what makes clothes and style great.

  3. William says:

    A lot of people are really against tucking in their pants with boots. I do it all the time during the winter months and get a lot of compliments on them. Out of my many shoe collections which spans from Common Projects, to Bally, to Prada, to Varvatos, my brown boot from Banana Republic gets the most compliments. Of course I don’t tuck in my suit pants but with my skinny denim or slim fitted twill khakis they look great.

  4. William says:

    Everyone also says unless you’re a fisherman or shoveling snow. Well everyone wears World War I and II influenced peacoats and trenches, but I doubt you served in the military. Or wearing nautical stripes makes you a fisherman. All in all, any man with confidence can wear a boot with there pants tucked in.

  5. Cooper says:

    A middle ground, perhaps?

  6. Chris says:

    I think it comes down to the simple fact, for myself, that unless you’re 6’5″ or taller, it really just makes you look kind of stumpy. Sadly, I’m nowhere near that threshold.

  7. Brandon says:

    By nature, all of the skinny denim I wear happens to fall inside the collar of my distressed Doc Marten’s. I don’t mind it one bit.

  8. Steve says:

    The only way I get away with tucking, without getting flack from my buddies, is when it’s raining. However, they are not very stylish so …. D

  9. steve says:

    hipster twat.

  10. steve says:

    hipster doofuses. Pull up your pants and keep them out of your shoes!

  11. Jesse says:

    Really this make you look like a hipster bum or a gang banger with those baggy pants. Let it go and keep it on the run way.

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  13. darren says:

    Of all the boots I have, it is my recent purchase (Cole Haan Sawyer Double Buckle…completely sold out on the site) that I enjoy doing this with. Tucking in is the only way to show them off.

  14. Jeremy+ says:

    If I am going to spend 150 dollars on some boots.. I am going to show them off to the fullest.

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