JonathanT Board

SHOES

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Florsheim Doon Chukka (affiliate link): The brown suede takes this from being a dress boot and turns it into the perfect High/Low option. You could wear them with a suit if you wanted to dress it down, or throw them on with a pair of jeans and a T shirt if you want to dress them up. $120

SHIRTS

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J Crew Slim Japanese Selvedge Chambray Shirt: I personally own this shirt and love it. It’s one of the only non-custom shirts I still have in my rotation and that’s because the fit is great and the chambray is extremely soft. It’s a light enough shade that it won’t look like a Canadian tuxedo when you wear it with the darker jeans below or your APC’s. $98

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J Crew Slim White Oxford Cloth Shirt: Same fit as the chambray above but in the versatility of a white OCBD. You can dress this up by tucking it in and throwing on a tie, or dress it down as far as throwing it on with some shorts and espadrilles. An OCBD really does cover the whole spectrum and is one of the most versatile shirts a man can own. $60

PANTS

Docker’s Alpha Khaki (aff link): These are the perfect balance between too baggy and too skinny. The color is also neutral enough that it will pair well with everything. Wear these the same as you would a pair of dark jeans. $68

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Flint & Tinder Denim on Demand: While ready-to-wear denim is great made-to-measure jean is probably going to be the best way to go. The guys doing the Denim-on-Demand jeans have been wildly successful with previous projects and getting a pair of selvedge jeans for $98 is a huge steal, let alone the fact that they’ll be made to your measurements. I recommend the slim fit and the Indigo Memphis wash. $98

Fall/Winter 2014

Jacket

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Frank & Oak Laurier Wool Navy Blazer: This is as simple and versatile as it gets. The warmer blue will be better with your coloring and none of the style details (lapels, pockets, etc.) are excessively trendy, meaning it will be timeless. It’s not flashy, but a Staple sport coat isn’t supposed to be. $175

Pants

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Frank & Oak Lincoln Twill Pants: I’d get these in the Army and Camel colors pictured above. They’re ideal for your coloring, the time of year, and their versatility. These are slim without being skinny. $55 each or $110 for both.

Shoes

Johnston & Murphy McGavock Boots (affiliate link): These are a bit pricey but well-made boots are worth it. They aren’t too dressy to be worn with jeans but not too casual to be worn with a suit, so a great, versatile pair of boots to last you all season. $250

Coat

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Frank & Oak Wool Herringbone Tweed Topcoat: This cloth perfectly straddles the line between casual and formal, so it can be worn over a suit or with a pair of jeans. The styling is also classic, meaning you’ll be able to get a lot of years out of it. $225