White's Boots
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I'm also toying with the triple sole, it works ok if you have big feet, with small feet they look like Frankenstein boots. 
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triple sole = insanity.  
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In my opinion (having worn both) the Whites are half a size bigger than the Red Wings. 
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So you're both saying that I should get a size 8? 
 I had a feeling you guys might say that, but now am sure.. Thanks! I have/had 4 pair of White's and probably 8 or more Red Wings. If someones experience with RW was with a moc toe boot then I guess I could agree the White's semi dress last may feel a half size bigger, but that RW moc toe is a narrow last. I will always buy my same size Red Wing as White's, 10.5D. I do not have a very voluminous foot but I am not a C width. Just my opinion. What Red Wings do you have? 
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My Red Wing experience is with GT's and the rough out chukka (forgot the model number). However, it is worth pointing out that there is quite a size/ fit difference between the Whites Semi Dress and the Oxford (I have both) of around half a size. I would match my Red Wing size for SD's, but go down half a size for Oxfords. Just my personal experience, if you want to be more sure, email Kyle at Bakers. 
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I think the only problem here is that there isn't really a "White's" fit. Oxfords, SD's and SJ's all fit very differently, which can have quite a bearing on choosing the right size. Same can be said of Red Wings. I can tell you what the Oxfords fit like in comparison to Red Wing GT's or Chukkas, I can't tell you what they fit like in comparison to Moc Toe Red Wings. Go to Kyle, we may all be (unintentionally) blowing smoke up your ass. 
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In my opinion (having worn both) the Whites are half a size bigger than the Red Wings. So, also bigger than the RW Chukkas?.. 
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In my opinion **Disclaimer, the opinion of the poster may not reflect reality in any form known by other humans. 
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^^^ i think it would help solve the problem cause the folks at White's could look at the template & say okay based on the measurements you sent in you are size ** width ** at least from the template they sent me it seemed to work like that. ah, the joys of e-commerce 






