1 Piece/3 Ways: The Wingtip Boot

December 15th, 2011

As we recently discussed, a complete wardrobe has boot styles for all types of occasions.

If you’re only going to invest in one boot for the season, however, I would recommend a lace-up wingtip brogue, like these badass chocolate brown “Daltons” by Allen Edmonds.

The trim leather sole, sharp toe and rich color make them appear dressy while the tall lace box, full broguing and toe medallion make them appropriate for casual wear as well.

Here’s three of the countless ways you could wear them.

1. Office Ready

If you’re wearing boots with a tailored look they need to look sharp (and polished) and the suit should be cut from a Fall/Winter weight fabric – think flannel, corduroy, tweed, moleskin, cashmere, etc.

With a suit, keep the boots laced tightly all the way to the top. This keeps them looking nice and clean and allows your trousers to fall over them naturally.

A wide 2″ cuff looks great on trim-cut trousers in heavier fabric and gives the hem a little weight, pulling the pant down and allowing it to drape properly. And no, you don’t need pleats to have a cuff – don’t be restricted by these old fashioned “rules”.

Bonus Tip: The shirt, tie and suit all have a flannel finish, which makes this outfit very soft, warm and comfortable.

Bonus Tip II: The more-versatile-than-you-think flannel double breasted suit again, as featured here.

Bonus Tip III: A single-breasted coat over a double-breasted suit is more visually appealing than the other way around. A DB coat just covers up all the layers of your outfit.

  • Leather wingtip boots by Allen Edmonds ·
  • Navy whipcord seersucker tie ·
  • Black check shirt ·
  • Navy cotton mac raincoat by APC ·
  • Oatmeal hand-knit scarf by Yokoo Scarves

2. Business Casual

It’s the perfect boot for business casual as well and looks awesome under a tweed trouser.

Bonus Tip: Sometimes I treat a lightweight jacket like a sweater – I like to leave it on to complete my look, even when I’m inside. It should be trim enough to fit under your heavier outerwear anyway.

Bonus Tip II: A corduroy tie is another one of those things that is a cross between formal and casual. Putting together elements of similar “appropriateness” is typically a recipe for a cohesive outfit.

  • Leather wingtip boots by Allen Edmonds ·
  • Glendplaid shirt ·
  • Red corduroy tie ·
  • Denim jacket by Levis Vintage ·
  • Navy peacoat Vintage naval issue

3. Smart Weekend

You can bring just about anything to a good tailor – even an oversized vintage parka. I bought this thing for a few dollars and had my man Franklin take-in the body and sleeves. Now it’s my go-to when mother nature is not messing around.

If you’re in NYC, I recommend you see Franklin at The Tailoring Room. He’s my personal alterations tailor and a good friend. You can tell him I sent you :)

Bonus Tip: The beauty of a neutral corduroy suit (like this one from my MAB by DT  Fall/Winter collection – more updates soon) is that you instantly have the perfect blazer and trouser separates.

Bonus Tip II: A fine gage turtleneck, dark jean, and classic blazer is a simple recipe for a refined look. More on that soon.

Bonus Tip III: Try going tonal with the pocket square. Think similar shade and similar weight – like this camel cashmere square with brown tipping.

Bonus Tip IV: Try tying your scarf in one simple knot like an ascot and letting it cover your body under a suit jacket or blazer.

Bonus Yip V: I’ve had several pairs of jeans cropped with no break, but it doesn’t mean they’re only good for loafers or lace-ups in the Spring/Summer. Come cold weather they sit perfectly on top of my boots, showing off their awesome detail.


  • Leather wingtip boots by Allen Edmonds ·
  • Khaki corduroy jacket (part of suit) ·
  • Forest green turtlneck by Uniqlo ·
  • Vintage olive parka ·
  • Fair isle knit scarf by Ralph Lauren ·
  • “New Standard” Raw denim jeans by APC ·
  • Canvas tote bag by Filson ·
  • Brown woven leather gloves by Hilts and Willard ·
  • Brown wool flannel pocket square by Armstrong & Wilson ·
  • Watch by Montblanc Timewalker

Thanks for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford.