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Men's Tailored Fit Sail Rigger Oxford Shirt

Item # 428017-A5X

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To order both a monogram and embroidery for this item, complete your order online with either the monogram or embroidery, then contact us before 10 p.m. CT on the same day to add the other personalization. Call 1-800-469-2222 or Text Chat now.

To add both a monogram and embroidery to this item, you must place your entire order by phone or online chat. Please call 1-800-469-2222 or text chat now. We apologize for any inconvenience.

Men's Tailored Fit Sail Rigger Oxford Shirt

Item # 428017-A5X

$21.99 - $39.00

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Allow 1-2 days extra for delivery of monogrammed items. The monogram and fee will be applied to the quantity selected with this item. To order multiples of this item with different monograms, please order items one at a time.

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Oxford like it used to be.

This is Oxford cloth done right. We developed an exclusive weave using thicker yarns to produce a heavyweight fabric true to the Oxford heritage. You’ll notice the substantial feel right away, and appreciate the way it gets naturally more comfortable wash after wash. Speaking of washing, we love the way this shirt looks right out of the dryer. Casually unpressed to give you an easy-wearing style without dragging out the ironing board (but we won’t hold it against you if you do). We’ve tailored it nicely as well, with a classic buttondown collar, gusseted side seams, adjustable two-button cuffs, rear collar button and locker loop. All this at a price that makes getting several colors almost a necessity. 100% cotton. Machine wash. Imported.


  • Exclusive basketweave Oxford cloth that’s soft, yet substantial
  • Classic buttondown collar
  • Gusseted side seam adds a distincitve touch
  • With adjustable two-button cuffs and sleeve placket button
  • Rear button keeps the collar in place
  • Tailored Fit: compared to Traditional Fit, it is 1 3/4″ smaller in the chest and 2 1/2″ smaller in the waist, with proportioned details
  • Monogram it! View all monogram thread color options 

More Information

Unfamiliar with a word? See the Lands’ End Glossary

` Fit & Size Information  |  Item Dimensions (.pdf)

Men's Tailored Fit Sail Rigger Oxford Shirt 4.7 5 14 14
sturdy and well priced The fit is only mildly tailored. I'm 6'1", 170# and a large regular is just right in body and sleeve length and in the shoulders, but rather loose in the sleeves, chest, and waist. A medium tall would probably fit me better but that and many other sizes were not available. The fabric is somewhat stiff after one washing, but it breathes well and looks like it will last. I bought this shirt in white as outerwear for sunny days and it suits that purpose well. I wouldn't call it a dress shirt. August 18, 2014
Good weight and size and colors. Repeat of above. August 3, 2014
Great shirt. The price makes it even better! This is my first oxford shirt purchase from Lands' End and I am very pleased with it. I was worried about choosing a size small, for I am usually in a medium, but by going by the size chart Lands' End has, it fit perfect! I am 6' athletic build and the tailored fit is just right for my build. The material is superb for the price, which I am very happy about. Upper end of quality but for a reasonable price. I will be purchasing more of these shirts. I also got it personalized and was also very happy with that as well. Thanks Lands' End! April 25, 2014
A Beautifully-Made Shirt in a Great Cut with Heavyweight Fabric I was really impressed with the quality of the Sail Rigger Oxford shirts when I found them at the local brick-and-mortar store last year. The Oxford cloth has a very good weight (heavier than my two Brooks Brothers Oxford shirts), but still has a nice, soft hand that feels comfortable and casual. Unfortunately, they only had the Traditional Fit (which looks very baggy on me) in stock, so I came online to buy this Tailored Fit version. The Tailored Fit's dimensions fit me much better. (For reference, I am 5'8", 150 lbs., athletic build with a ~40 inch chest measurement. The Small is perfect.) It sits closer to the body around the chest and waist, but still has room enough to look casual untucked (which is how I usually wear my sport shirts). The fit is similar to that of the Canvas line shirts I have (although the Tailored Fit might be just slightly trimmer.) These are definitely casual shirts. The weight and slightly rough texture of the basketweave make it a bit too rugged for business casual, IMO. Lands' End still makes the Hyde Park Oxford (with the same Supima cotton as Brooks Brothers uses on many of their better quality shirts), and those are a better option than the Sail Rigger for business wear. (The Hyde Park is also longer in the body, making it better for tucking in.) I have the Fresh Pink, White, and Blue Jay. The White and Blue Jay are made in China, and of the same beefy fabric that caught my eye in the store. The Fresh Pink is made in Malaysia and of slightly less weighty fabric, but still of good quality, especially in this price range. These compete with shirts than cost twice as much. March 31, 2014
Great feel, great fit (if you're a little husky) I love these shirts. I now own 4 of them and I might buy more. I'm a little short and a little stocky, and these are very flattering and comfortable on me. Quality is solid, fit is solid, they're very versatile - all around a great shirt. One of my two favorite LE items so far. March 15, 2014
Right material, odd cut This gets back to the kind of material and style I used to have and enjoy in an Oxford shirt. But what's with these gigantic arm holes? Did someone take the "sail" description too literally? I feel like a flying squirrel, with all that extra material. Also, the second button is placed too high. No one wears a tie with this shirt, so the second button defines where the shirt opens at the neck. To open properly, the button should be half an inch lower (as it is on the old shirts I was hoping this would be able to replace). The proper balance between the stand-up of a button-down collar and the angle of the placket around the one-button-undone opening is crucial. Fix those two things, and I'd order several more. Especially with a wider range of colors, such as light yellow and light gray. As it is, I'll just enjoy this one. January 14, 2014
Great shirt. Ordered this shirt for my son. He loves it. I also ordered two of these for my self, the feel of the shirt was great and sizing was good. January 6, 2014
Good Quality Sport Button Down at a Reasonable Price This shirt is exactly what I want in a casual button down. The material is slightly heavier than a typical oxford and seems to come out of the dryer in good shape. I wear it without using an iron. It also fits me just the way I like. I am 5'!!",weigh about 170 and wear a 32 waist in pants and a 40 to 42 regular in a sport coat. The cut of this shirt is slim and creates a fitted feel that is just right, not to tight and not to loose. The quality also seems very good and the sleeve length is just right for me. I buy a 34 inch sleeve in a tailored shirt. The shirt has been through the wash a couple of times with no change in size or appearance. December 8, 2013
I like this shirt I like Oxford cloth shirts, and I've been wearing them for more than 50 years. It's hard to find Oxford cloth in sport shorts with lots of color. Land's End has produced a really good one here. The two I received are destined to be my favorite shirts to wear with blue jeans or khakis. A few critiques. They're advertised as being heavy Oxford cloth, but I would call them medium weight. The size runs just slightly big. If you're between two sizes, maybe you should pick the smaller. The last time I ordered an oxford cloth shirt from Land's End the the shirt tail was too short. These have good, long tails. I hope Land's End will add additional colors and patterns to this shirt and, if so, I may order a couple more. August 14, 2013
Great fit, very comfortable, high quality Excellent shirt for casual event or summer business wear. August 5, 2013
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