8 Ways To Wear Khaki Pants | Chinos With Boots, Loafers & Sneakers

8 Ways To Wear Khaki Pants | Chinos With Boots, Loafers & Sneakers


What’s up, guys? I’m Brian Sacawa, you’re
watching He Spoke Style, and today I’m showing you eight ways to wear khaki
pants. First up is a look that I showcased on
the website six years ago. Kind of hard to believe. And that I can still wear
today is a testament to the fact that great basics never go out of style. Have
the khaki pants that I’ll be featuring throughout this video and they are from
bonobos. I would call this the Goldilocks fit. Not too slim. Not too baggy. But just
right. Up top, two more staple items. A heather gray athletic sweatshirt by
Levi’s worn over a classic OCBD. Accessories. Simple and elegant watch on
the wrist. Sunglasses are by Oliver Peoples. These are the Banks. And then
finished off with a pair of white Common Projects sneakers. Next, we have basically
the same look although I have upgraded it a little bit to give it more of a
business casual feel as opposed to the more casual vibe of the previous outfit.
So, two changes here. First, swapping the athletic sweatshirt for a merino wool
v-neck sweater. This is by J.Crew. And, again, worn over the same light blue OCBD.
Other change is the shoes. I traded the white sneakers for these penny loafers
by Allen Edmonds. With only two simple changes, I was able to transform a more
sporty outfit into one that I would say fits pretty well into that kind of hard
to define business or smart casual category. Here we have a look that if it
was 2012 or 2013 would totally break the internet. This is, of course, a menswear
uniform of sorts. It’s so classic. It’s so easy to put together.
And it really has you covered in many, many different types of situations.
Breaking it down. First, the navy jacket from Michael Andrews Bespoke. Hopsack
fabric and patch pockets give it a more casual, laid-back feel. Underneath, once
again, is the light blue OCBD. And then anchored by a pair of Allen Edmonds
lace-ups. I’ll be honest and say that it’s been a while since I’ve worn this
particular look. But styling it for this video reminded me how powerful a simple
and classic look like this can be. If you haven’t noticed, we’ve sort of been
ramping up the formality with just some minor changes to the basic look we
started with. And here is the last in that series before we change things up a
little bit. This is a really classic, conservative, and for lack of a better
term, what I would call a very “American” kind
of look. It’s got this kind of college-prep thing going on. And I really
dressed it up, of course, with the tie. Classic Brooks Brothers BB #4
rip tie. And then instead of a button-down collar, we have a spread
collar shirt. Now, because I was thinking along the more preppy lines here, I
decided to finish the look off with a pair of tassel loafers. These are by
Johnston and Murphy. Moving on now to a look that I would put in sort of the
grown-up casual category but really is a look that would look great on anyone
pretty much any day of the week. Khaki pants, because they are such a classic
and staple pair of pants, I love pairing them with other classic items and a very
classic menswear color palette. Here, I’m doing that by keeping it a little sporty
up top with this navy rugby shirt. It’s from the Nordstrom 1901 line. And
then the piece that I would say makes it a little more grown-up, this brown suede
jacket, which I picked up at Billy Reed a number of years ago at a very deep
discount. And then keeping the sporty theme going by finishing off with a pair
of white Common Projects. Here’s a look that is both simple and casually cool.
It’s always good to remember, especially as you get deeper and deeper into
menswear and developing your wardrobe, that, as I said before, there is power in
simplicity. The more you learn, you know, it’s kind of easy to get bored with that.
But when you actually get back to basics, you really understand, frankly, why it
works so well. Here, I’m just keeping it very simple with a white OCBD. And then
for some contrast and a little bit of casual edge, I threw on this black Levi’s
denim trucker jacket. Shoes, or actually boots, I should say, are my leather
chelseas by Jack Erwin. Super comfortable, which is why I like to call
chelsea boots the loafers of the boot world.
Up next is a look that’s all about playing around with different shades of
brown. I would say this is monochromatic- ish only because the lighter khaki color
kind of makes the monochromatic thing a little less obvious. Dressing tonally
like this, it’s always great to add in some texture, which is what I did with
the suede trucker jacket. Really killer piece from the HSS Michael Andrews
collection. Link to sign up for the launch announcement is right
up there. Underneath, keeping it casually elegant with the brown turtleneck. It’s
by Ted Baker. And then a great accessory that really makes the outfit, in my
opinion, a patterned scarf by Drake’s. And then, once again, finished off with the
leather chelsea boots. Finally, an outfit that I’m calling the urban explorer. What
I want you to think about here is to actually imagine what this outfit would
look like without the waistcoat. I think it would still look fine, but the
waistcoat definitely takes it up to a different level, which is always the case
when you’re adding a tailored element into an otherwise mostly casual outfit.
Speaking of the casual side of this, let’s talk about the shirt. This is a
Western denim shirt. It’s by Polo Ralph Lauren. Notice the snaps instead of buttons. Up top, an olive green felt hat. It’s by Worth and Worth. And then,
anchored by this great chocolate wingtip leather dress boot. This, of course, the
Dalton by Allen Edmonds. So there you have it. Just eight of the many ways to
style khaki pants. As always, complete outfit details are down below in the
description. Leave a comment. Let me know which look you liked best. Thumbs up. Don’t
forget to subscribe. And until next time, thanks for watching and stay tailored.

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83 Comments

  1. #early
    – i remember #1 from when I started following HSS. great, casual look! #2 is a more mature version of #1
    – #3 and 4 are fine smart casual outfits. looking great!
    – #5 has a great direction, but the polo and jacket you featured aren't my cup of tea
    – #6 is another cool, casual look. #7 – i love monochromes, it exudes a level of style maturity. that suede jacket is killer!
    – #8 is a look that is very Brian Sacawa haha. idk if i can ever pull off smth like that. and i think it will look better on you with the sleeves folded up!
    Cheers man!

  2. Super outfits 2, 3, 6, 7, rock my boat. J&M loafers sit flat on the floor, perfect, only prob with AE shoes is they curl up at the toe. great news with the 80K

  3. Great combinations. All looks are well put together. 👍
    Love that brown jacket. It’s gotta feel amazing too.
    Cheers 🥂

  4. Hey Brian. I have been into style for a number of years, but now I finally wanna look towards purchasing proper leather shoes (i.e. blake stitch/goodyear welt). could you recommend a few AFFORDABLE brands that I could look into as i get started in this area, please? thanks in advance!

  5. 80k subscribers!! Let's go Brian, you're rockin the internet! Awesome video as always, my favorite outift was n.6, simple but for me the best one.

  6. I love your dexterity in combining these outfits. I'd wear almost all of them!
    With all your different shoes, I've been wondering: In what timeframe did you gather your footwear? It's an impressive range, and given the price tag of e.g. Allen Edmonds, it also appears to be an expensive one. Doesn't seem like a collection to be put together quickly to me!

  7. Nevermind the khaki pants (styled really well with these eight outfits) you wore the tan long sleeved polo over a denim shirt?! Very cheeky! Works really well though…

  8. Hah! I'm wearing the very same khakis as I watch this. It's my go-to bottoms. And I prefer a button-down white shirt instead (goes better with my complexion). Albeit I would have gone with the Rolex instead of the Vacheron as it's less formal. Great video as usual!

  9. Khaki and grey, a very underrated color combo IMO. As with all your lookbooks, I wouldn't hesitate to wear any of them. Thx for the casual elegance!

  10. just got myself a pair of khakis, almost exactly like the one you have! Thanks for the tips, will most definitely use them in the future.

  11. Ah, you made me look at khaki pants in the online store…. should I go for it? I knew I shouldn't have clicked on this video. Great job, Brian!

  12. Great video Brian. I have abandoned my khakis outfits , don’t ask why lol. Time to go back and step it up . These outfits are amazing. Classic, simple, elegant doesn’t get any better 👍

  13. Your entire channel is just a style masterclass. You're a rare gem in menswear.

    P.S: While look #6 looked effortlessly stylish, look #7 was simply breathtaking!

  14. That Billy Reid suede jacket is the boots!!
    I like the look with the navy jacket, repp tie and the tassel loafers. Chelseas would work too since the weather is getting colder.
    That collared sweater you had on at your desk paired with the collared shirt is another unsung look that works well. I have several vintage Polo collared wool sweaters I wear the same way. I would triple that with the BR suede jacket or a cord blazer to go ultra-rustic and add another layer if warmth if needed. Rugby shirts are also a great layer to wear this time of year (I have several worn in rotation I wear in business casual environs).
    I also own an earth-toned canvas JCrew barn coat with a flannel lining & contrasting cord collar I've worn many a season until the top of the patch pockets have frayed but I can't bring myself to retire it or move it to lesser duty. I wear it with a heavy wool sweater or a snap-button Eddie Bauer feather down jacket underneath when the temps get below 30° F here in Ohio.
    Thanks for your posts-gives me good upscale aspirations to adopt into my own lifestyle.

  15. Hey Brian, what size are you in the Ralph Lauren Western denim shirt? Fit is incredible. Also is the hat from worth and worth still available?

  16. Look #6 the easy weekend, an awesome look, and now I finally know how to pair a black denim jacket. I got one 2 weeks ago and was trying to figure out what to pair it with.
    Thanks Brian!

  17. Awesome looks Brin! This is probably your most practical look book yet. Nearly everyone wears khaki pants. Keep up the good work.

  18. Regarding the suege jacket in the #7 outfit, what is an acceptable length? Seems like a few inches below the waist, but what if you have a higher rise pant?

  19. Thank you so much Brian, I just started following you here and on your blog a few months ago. I've learned so much and you have helped me improve my wardrobe and style! I'm not sure how old you are, but I'm in my late 40's. One of my fears is looking like I'm "trying too hard" or dressing too young for my age. With the looks you've shown here, would you discourage me from any of them given my age (specifically the white tennis shoes) or I am safe with styling similar looks in my late forties? Thanks, man!

  20. Great looks as usual! I love chinos because of their versatility but I've found I usually feel more comfortable wearing darker ones to keep the attention higher up. I guess khaki/beige pants work fine in the summer for me too though! I liked looks 3 through 5 best by the way.

  21. Loved the commentary on this vid, man. You’re just stating each outfit as it is. The “this would’ve broken the internet in 2012” bit was hilariously accurate. Great vibe.

    Edit: Woah! That’s a nice looking polo sweater at the end.

  22. Really enjoy your videos as they are very informative and helpful for guys like me…older… Can't wait until I hit my goal weight so I can finally change up my wardrobe. Thanks, and keep up the great videos!!

  23. Is khaki flat-front with crisp center crease and 1 to 1.5 " cuff doable? My signature look when younger, beltless with side adjusters; your take please..

  24. I’ve been at a loss to explain why I love this channel but I think I’ve figured it out. Brian has perfected the art of subtle style; being stylish without having to resort to the ‘look at me!’ approach such as too many accessories, too many buttons undone (a.k.a., the Alpha M), and so on.

  25. Great video, Brian. Purchased a pair of the Bonobos Chinos in the Tailored fit. I got an inseam of 28. The alternative was 30 which I knew would be too long. The bottom of the pants barely cover the top of the shoe. Noticed in your video you had a slight break. By the way, the sales person said the length was perfect and “this isn’t 2005”. Thoughts on inseam length?

  26. Hi, I really love your channel! Sadly though, I'm from a tropical countries and temperatures are above 30C/90F year-round, so I can't wear many of your outfits. Are there be any outfits you recommend for this type of climate?

  27. Hi Brian ! Sorry for my not very good English (I'm living in France) but thank you very much for sharing all these videos ! They are all very inspiring and of very good quality ! Please continue like this 🙂

  28. I am fair skinned so the grey over khaki wouldn’t look good on me. I do think for guys over 40, myself included, the prep look is a great business casual look and just a personal casual style. No pleats though!

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