It’s not heavy duty outerwear season yet, but it’s time to start layering on some weight.
As you may already know, I’m a big fan of wearing chunky sweaters, especially cardigans, as outerwear.
Here, I put together three looks using one of my favorites. With a shawl collar and a belt, it has an awesome trench coat x bath robe feel, which makes it easy to dress up or down.
1. Tailored for the Winter

A sweater is meant to fit snug, so as a jacket it’s going to look very fitted. This makes it perfect for throwing over a tailored look – like a waistcoat and trousers.
Tailored garments in winter fabrics – like this wide wale corduroy suit, plaid flannel shirt and wool herringbone tie – can take you pretty far into the season without heavy outerwear.
Bonus Tip: A felt bag is a perfect match for wool accessories.
Bonus Tip II: Flannels aren’t all oversized casual shirts, there is a new breed of superfine flannel shirting that has instantly become my go-to this Fall.

Bonus Tip III: A light natural leather shoe is perfect for autumn.

- Grey herringbone tweed tie by Woolrich
- Grey felt/leather briefcase by Graf & Lantz
- Tan leather monkstraps by Scarpe di Bianco
- Grey flannel check shirt by Michael Andrews Bespoke
- Watch by Montblanc Timewalker Automatic (42mm)
- Navy corduroy waistcoat (part of suit) by Michael Andrews Bespoke
- Navy corduroy suit trousers by Michael Andrews Bespoke
- Chunky belted cardigan by Ralph Lauren Polo
- Brown alligator watch band by Montblanc


39 Comments Add a comment
This has got to make you smile: http://www.esquire.com/blogs/mens-fashion/band-of-outsiders-show-nyfw-2012
Another groundbreaking post bro. The Borsalino hat on the second look kept people talking almost more than your fur collar post! Completely innovative. Posts like this really keep me on my feet on how I can add head turners into my own style…
http://urbanaesthetics.net/
I need in my life those Double monkstraps by Scarpe di Bianco. well done sir!
Bravo. You are effortlessly summoning the ages with that Norfolk jacket. It seems a slight feminine in knitwear. However the looseness of that wide hat brim is very forward for such classic menswear and worth a note of mention. I would say it might do your look justice to choose only one styled item to wear at a time. A dandy flaunts all but modesty.
Best of luck with your fashion experimentation,
Joaquin
Burton-On-Trent
The hat in 2nd look is so innovative. Where do you come up with this stuff?
I think it’s all about confidence. If I saw a guy wearing a hat like this, but wearing it with confidence, I would be jealous of that swagger. which it seems some readers have voiced
the look with the hat is appalling, really… i mean it. you look like an olsen twin. Man up! if you are going for the old italian hat look this http://images.thesartorialist.com/photos/9248VEOldMilanoWeb.jpg although it wouldn’t go with the feminine robe. The robe makes you look frail some how. But I i think you do so many things right on this site. well C’est la vie
Some love it, some hate it.
Keep in mind we purposely think outside the box to get people thinking and talking. I have a version of every piece that old man is wearing – they’re classics – but if I offered such an outfit, what would be the point? There’s no innovation, and nothing to drive discussion.
I’ve said this before – as a stylist I could easily put together basic, classic “well dressed” looks that resonate with the majority of men, but what’s the point…where’s the fun in that?
Don’t be afraid to do YOU…you’re not the same as everyone else…
Thanks for reading,
SB
^ WELL SAID SB!!. when i first looked at the picture of the hat i automatic thought of ways where i can add mt style and switch some things around. thats the point of Dan doing this YOB to inspire us to do US with a new concept if we choose to accept it.
The downside of mens blogging is all the haters. I mean guys come to this site to enjoy free content (some of the best on the internet) and leave comments like this? Whats wrong with people.
Keep doing you and signing checks Dan
I don’t think in order to drive fashion forward us guys need to progressively begin to wear women’s clothes. It may not be technically a woman’s hat, but that hat looks like something my great aunt would wear.
The Borsalino is a classic men’s hat. The idea is to think outside the box – not dress like me.
Do you.
Thanks for reading,
Dan
Well said! I concede, I have to say I do like your site, and the hat is growing on me, slowly lol
Some stuff you hit spot on and others are a total miss. But the haters are gonna hate so keep blogging!
Okay, if we do year-end poll on best looks of 2011, I’m not sure your Scarecrow hat
will come out toward the top. But I don’t want to stifle your sense of adventure.
Phil
Your boys may give you shit for that hat, but I bet all the ladies at the bridge game think it’s fantastic!
Hahaha. Yea the ladies love it…especially the elderly ones
Thx for reading,
Dan
Not a fan of the hat but that’s only because I look ridiculous in any and all hats. Love the layer cake look, it’s completely fantastic.
Love the sweater, hate the hat!
Dan,
Bravo on the last look.
@cam Ebay, vintage rolex, enough said.
i was going to donate my hunter green toggle coat.but this i think i can pull off a look olike this.thanks tsb.
Does your girlfriend get upset when you wear her hat?
Steve,
Didn’t I teach you not to be mean. That’s the reason why you don’t have a girlfriend, you’re sitting at home and alone every Friday and Saturday night.
Grow up Steve. And if you’re going to post a comment like that. At least be funny !!! Oh yeah and Steve, why don’t you start your own blog and show us how to really dress. 29 years old: no girlfriend, no job, and living in your mother’s basement rent free. You’re a real winner!!! Hurray for Steve everyone. Woo hoo. !!!
Hahahahha!! Listen to your mother, Steve.
Ouch !!!
I really need to start implementing this anti-bullying tactic over at Unabashedly Prep. Kind of amazing.
Great work Dan!!
Really feelin’ the cord vest+ plaid shirt…
I like your reasoning for rocking the hat that way. (I always try to think of things like that if I don’t quite like something about a piece, glad to know I’m not alone:))
I love how you played off that tree in the last look ha, some rich colour going on there!
(Oh yeah, and great use of the sweater, lol)
@alex – stunning photography!
@dan – i am in the market for a dress watch within the $1000-1500 price range. any thoughts? nice post btw
liking the facial hair!
I love your Autumn Layer Cake. The orange pants are a great accent to that belted coat. It makes the subtle print “pop”.
xoxo
http://www.thewrittenrunway.com
This is another great post. I had a feeling you’d be doing a post on this cardigan since you wear it a lot.
The quality of the pictures have become much better in the last few posts. Many people used to complain that the pictures were overexposed, but they just about perfect now. Your readers will enjoy each post a lot more with better quality pictures like you have here.
Again, great work to you and the rest of the SB team!
hey Dan good post. im feeling the old italian guy swag. although i would rock a newspaper boy hat or a different style fedora. i can see why you get shit from your boys regarding the hat. not to disrepect or anything but i was reminded of my grandma. again keep doing you and inspiring me to do me.
-BBQSANCHEZ
Funny thing, yesterday I had on the same concept as outfit 1; waistcoat and trousers. But my chunky sweater didn’t have a belt. lol.
Outfit 3′s color palette is on point! Not to mention the scenery. Green fence, orange/brownish leaves. Nice job
that last outfit.
damn.
NT dressing better thread shoutout!
Love that toggle coat by club Monaco. I called every location and they sold out. It’s one piece I’d love to have. Anyhow, great post, I’m not digging the hat but u can pull it off ha
I’ve got a size small for sale.
Those chukka boots have an amazing colour, and the hat is definitely unique.
Genial!
I love the 3rd one!
Awesome pats!
;-)