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.

    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.

    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.


    • JP

      Will these boots pair well with black/navy/charcoal outerwear??
      What color is your pea coat in the Wednesday look; navy or black?

    • john

      Wow, I just purchased some black wingtip boots by John Varvatos, but I really like the ones you have here. I must not be the only one that loves these. I was looking for some tips on how to wear them and really found some great things on this post. Everything was very well put together. Thanks!

    • Tony

      Really like the looks here Dan. Happy holidays.

    • Mondo D’Swagu

      Nice boots….I have a pair of navy blue ankle brogue boots….the sh@t of legend.

    • Sergio Arteaga

      *sigh* tell me why the next day I walk into Cole Haan and purchased the Cole Haan Air Colton Wingtip Boot:

      • Sergio Arteaga

        …saw Dan with them at MAB the AE’s and was definitely what put me over the edge on purchasing some dress boots.

    • steezus christ

      This is a great post. This is why I see no reason to read GQ or Esquire. Thank you.

      • Mr. Andy

        If I was editor-in-chief of either I’d be shitting my pants about now.

        • http://www.thestyleblogger.com SB

          haha. or at least taking me for coffee

          Thx for reading. Plenty more to come.


    • JR

      Are these the “Dark Chocolate Calf” Allen-Edmonds Dalton?

      • http://www.thestyleblogger.com SB

        Yes, my apologies, these are the dark chocolate calf – not cordovan. I updated the post.


    • Chris

      Hi SB I’ve got a question about boots for you – do you agree or disagree with the “boot tuck”? Since you get your jeans cropped you don’t need to do it but I’ve seen you do it in the past, have you gone off it or do you still like to do it?

      Many thanks.

    • RH

      Great post. Love those boots and how versatile they are. I gave them a long, hard look and went with something else. Love what I got but still wishing I had those AE boots in the rotation.

    • Windsor

      Dammm that Sunday look is Amazing!! – However, I would pair that with your white Nike high top sneakers – that would be even better :)

    • MOZART5000

      Quick question SB- For your friday look, are your jeans shorter than normal? As far as I could tell they weren’t tucked into your boots. Do you have specific jeans that you only were with boots like this? Loved the Monday and Friday looks.

    • BLSesq.

      Some great looks, especially Monday and Sunday. I just picked up a pair of Hamiltons by Sebago today, and you definitely provided some great suggestions for how to work them into my rotation.

      • Don

        I really like those Hamilton boots by Sebago. Do you know where in NYC I will be able to purchse a pair?

    • Johnny

      Hey Dan, i’m loving the blog and i’ve been wondering what kind of product do you put in your hair; i know its a bit off but i’ve been using gel and it just gets really hard and flaky and I HATE It, so i was wondering what do you use?

      • Arron

        I’m not sure what kind he uses but I am a hairstylist and I would say anything by American crew would work well. I use difi by American crew and it works really well. Also check out layrite (a company in orange county,ca) you can order their pomade online.Also if you are looking for something cheaper axe makes a good one for six bucks, just go to target or even cvs!

    • cam

      hay dan, are these some type of “limited edition”? i don’t see this color on their web-site. that fur-lined RL vest is boss. -best

    • Evan

      What made you decide on Allen Edmonds instead of Alden? I loved the post but always prefer the latter.

    • HarrisonK

      The funny thing is, I just ordered two pairs of AE and am eyeing the Dalton (since I don’t have a pair of boots besides for bean boots). I was also one of the ones who asked for a ski post, and the “70s Aspen style” look is great.

      Great post, I look forward to more.

      • HarrisonK

        Also, Dan, the Dalton only comes in the Cordovan version in a light brown color called “Walnut” so it appears that you have the “dark chocolate calf”. Although, I could be wrong if you got a cordovan version that isn’t offered anymore, or isn’t offered yet.

        • http://www.thestyleblogger.com SB

          You are right. They aren’t cordovan – chocolate brown calf.

          Thanks for reading,

    • Anonymous

      WOW. LOVE this post. SB at his finest. Best on the net, hands down.

    • TO

      Knocked it out the park with these looks my friend. Styling is next level, really.

    • chet

      i think you mean “Dalton”

      • http://www.thestyleblogger.com SB

        Yup. Dalton. Sorry for the typo.

        Thx for reading,

    • Vidal

      Another killer post. Timely as always. The minute AE decides to give us bigger guys some love I’m copping a pair of these. I’ve been eyeing them for a while, but unfortunately they are not available in sz 16. Any suggestion for a shoe/boot maker that does offer a brogue boot in a 16 or 17? For now I’m planning on grabbing some Donald J. Pliner chelsea boots, but will continue to covet these until a suitable alternative comes my way.
      Looking forward to more info on ‘MAB by DT’!

      Peace and blessings,

    • Gary-A

      It’s official: Allen Edmonds are endorsed by TSB and are therefore cool again. Style Forum members shed tears of disappointment.

    • Ambyr

      These wingtips are so pretty, the color is amazing. I’m loving your Wednesday and Sunday looks. Easy and sophisticated.


    • B.Murray

      How much are these boots and where is the best place to find them? Also, will this look still work with guys with a more box frame (ie. Football/muscular)? Any insight you could provide would be great.

      • HarrisonK

        AE sells “seconds” at their outlets and their shoe banks. You can get the Dalton boot for about $375, or if you want the second, you can get them for $299.

    • Emanuel Iuhas

      Thank you!