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Dressing Dudes: The Speakeasy Edition

June 29, 2009

L-A: So, I have no idea if Ally will be joining me on this post or if she’s still skipping through the aisles of the Digby Frenchy’s.  Since it may be a solo post, I’m going to continue on being giddy with power and post about Sandra Bullock’s cute outfits and Ryan Reynolds’ (aka. Mr. Johansson) hotness in The Proposal. Although, at second glance, I’m not going to bother (the outfit doesn’t look as cute in that photo, although Ryan Reynolds is still hot). Instead, I’m going to take a cue from a recent Trend Alert on Refinery 29 that focused on a resurgance of the style of Buster Keaton.


(images via refinery29)

mkkkkkkkkk (sorry, that’s my cat jumping on the keyboard to say that he approves of the look. or that he’d like me to move my macbook and make room for him. hard to say).

This coincided nicely with some other recent internet finds, particularly photos by the Sartorialist of the Jazz Age Lawn Party held earlier in June on Governors Island in NYC. It all made me want to throw on a cute dress, a cloche and dance the Charleston atop a flagpole.


(image via The Sartorialist)

In other words, it made me want to share some ideas on how dudes can look dapper if they take some cues from the Roaring 20s. And note, the keyword there is “cue”. You want to look stylish, not like you’re headed to a costume party or you’re an extra escaped from the set of the Great Gatsby.  So let’s start with some more Buster Keaton:


(images via If it’s hip, it’s here)

Jason Segal was dressed to look like Buster Keaton in April’s Vanity Fair, and the whole look is deceptively simple and can be made to be less costumey. Of course, you have to have enough chutzpah to work that hat into your look, but if you’re not interested in that, you can always just go for the shoes.  Thanks to one of my new favourite fashion sites, Nerd Boyfriend, I figured out that you could pick up something like Chronicles of Never’s 5th Chapter boot:


Sadly, I can’t find these boots online. They appear to be sold out from the one spot that I know for sure carried them. But Ssense out of Montreal does carry Chronicles of Never shoes. Or you can just look for something similar when you’re out shoe shopping.

And some more examples of how to rock the Jazz Age look via Mr. The Sartorialist:


Again, the hat might be a bit much for everyday, but you could wear everything else to a summer wedding (try a linen suit) and look très sharp. Or try this chap’s outfit for kicking around on the weekend:


This one is all in the hat and shoes and I quite like it. But when you wear a hat, you need to own it. You need to be thinking, “I look awesome in this chapeau.”


(images via refinery29)

Those fellows are not worried about how their hat looks. They are secure in their hats and how they look.

Another way to work this speakeasy style is to work a bow tie into your outfit.


Okay, sure, this particular look by Lova Designs does require one to be skinny and young, but you could do something similar (as an aside, what is it with the sick looking model. And I mean sick as in palid and unhealthy. He looks like he needs a good meal and a nap. Are there not better looking models available?) . Or you could pair your bow tie with a linen suit. Russell Smith has some helpful thoughts on the bow tie and who can wear it (everyone) and how they can do it without looking nerdy (don’t be ironic).

Now, if you’ll excuse me, I’ve got some bathtub gin to check on.



AllyG: I am in fact back from my Frenchy’s journey, however I have officially turned a corner in my self-absorbed life path. I spent $37.50 on baby clothes and $0.00 on clothes for myself. I recognize that this post is dangerously verging on “writing about onesies!” which my boss claims will happen next Fall (I promise you it won’t). I am merely stating that I am now incorporating, “Thinking of Others” into my daily routine (that, and I am too large to look at the regular sized bins and the maternity section at Frenchy’s le sucks le hard).

Anyhoo, you have NO IDEA how glad I am L-A started a post. We got home late afternoon yesterday with me feeling like a bag of poo-poo. I have reached the milestone in pregnancy where I have to switch sides every five minutes throughout the night due to hips that feel like they are on fire. Yes, I realize this is a fashion blog but I need a place to vent. Anyway, here I am sitting with my DECAF tea, frizzy hair, and “old lady shoes” (as my husband refers to them…incidentally, my mother bought them for me at Frenchy’s). They look like this, but in pink:


Back to the subject at hand. Dressing men. Now, some men argue that spending money on clothes is ridiculous and a complete budgetary waste. I point to a recent article in The Globe and Mail that tells gents how to be not only fabulous, but thrifty.

I agree with L-A. Men need to have confidence when veering from the Dockers and Dress Shirt Uniform. Especially when it comes to hats. More men should rock the newsboy or the fedora. Except Zac Efron. Zac should remove the fedora immediatley.


This is how you do business casual with a hat. Loved the rolled up jeans. Fantastic extra touch.


Another trend I’d like to see build momentum is bringing back the well-tailored suit on men under 60. You just don’t see it often. Suits are intimdating, I get it, but they also class you up like ordering a pinotage at the Argyle while out on a bender. I found a great blog for men who want to dip their toes into suit wearing. And yes, suits are indeed investment pieces. You don’t have to be super skinny to wear the slim suit (ah, gender equality, finally fashion items that males can be self-conscious about…kidding…sort of…not really). You know who does the tailored suit so very, very well?
See? It’s easy, boys!

I am going to now return to my decaf and proceed to overheat for the next eight hours.


6 Comments leave one →
  1. June 29, 2009 9:16 am

    Another awesome post – as always.

    May I ask a quick question?

    I was in Banana Republic the other day, and they have cuffed pants – what’s the verdict on that, oh wise ones. Hot or not?!?


  2. allygarbs permalink*
    June 29, 2009 9:24 am

    Martin, those are delicious pants. I am a big fan of the cuffs. You need to return to the Banana and purchase them immediately. Seriously, I’ll cover for you at work. Also, do you remember when Jack from Will and Grace worked at The Banana? Such a funny episode.

  3. L-A permalink*
    June 29, 2009 9:37 am

    I agree – those are great pants. Nothing wrong with a cuff on men’s pants. Even GQ agrees with me ( GQ says that it should be flat front trouser if you’re going to have cuffs and it should never be on evening trousers.

    I think you just want to avoid looking like you’ve pinned and rolled your pants, à la late 80s/early 90s. Some more tips on the cuff:

  4. June 29, 2009 4:33 pm

    hmmm – well you are both very persuasive. (Love the Will & Grace reference). That GQ article quotes a very interesting side-benefit – that cuffs catch loose change. Never thought of that. How handy. If I’m stuck for change, I can simply reach down, and find lunch and ferry money in my cuffs:)

  5. June 29, 2009 6:54 pm

    i’ve said it before, but we can all thank justin timberlake for bringing sexy back. i’m serious. the baggy/casual look has been fading ever since. and i’m happy, very happy about this. more tailored, slim-fitted (if not fitted) attire!

    now where’s my tailor….


  1. Yay or Nay: dudes rolling up their jeans « Fashionable People, Questionable Things

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