Who Wore It Better: The Tailored Khaki Trouser

Like we said before in our preppy post, khaki is one of the colors everyone should absolutely own in their wardrobe.  However, sometimes buying “off the rack” doesn’t help.  Everyone has a different body type, so what works for one may not work on the other.  So for this challenge, we both took a pair of khakis , tailored them and then put on a quick outfit to show you just how amazingly diverse and amazing khaki trousers are.  And as always, we’d like to know which style you liked better.

1.  The Private School Uniform


Raj loves his high school, Spencerville Adventist Academy.  In fact, he still wears the oxford shirt he had from those days!  It’s a simple light blue oxford shirt that can still be worn with a variety of styles.  Here, he wears the preppy quilted vest and the tailored pair of khakis.  Just like me, he has no break in the pants and they taper very well to go along with his skinny legs.  Worn with them are a pair of black cap-toe monkstraps that is just lovely.  It’s a very casual yet clean look.




Oxford Shirt by SAA, Quilted Vest by J. Crew, Khaki Trousers by J. Crew

Sunglasses by Banana Republic, Socks by J. Crew, Black Monkstraps by Johnston Murphy

2. The Sprezzy Italian


I decided to wear both khaki pants and a khaki jacket (a lighter khaki) for this look.  Heck, even my tassel loafers are a shade of khaki.  My main contrast in the outfit is the light navy shirt. The lack of tie and the open double breasted jacket really make the casual look (hence the sprezza).  What’s interesting to note is that the jacket has a narrow button stance reminiscent of the 1960’s but very wide peak lapels (1940’s).  It’s made of pure cotton, making it a very, very lightweight summer jacket.  The pants, just like Rajesh’s are tapered and hemmed up for no break.





Cotton Double Breasted Jacket from Suit Supply, Blue Shirt from H&M, Khaki Trousers from Banana Republic

Tassel Loafers from Aldo Shoes 

You should be sold by the khakis by now.  They go with literally everything.  Also, invest in a good tailor! We’re going to be talking about the importance of having a tailor soon, so be on the watch for that article!

So which outfit do you think was the best?


Ethan W. 

Street x Sprezza

Photography by Ethan W.

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