My Favorite Outfits: Cold Weather Smart Casual

This has been one of my go-to outfits all winter long. It's more than casual but not quite dressy. Perfect for Mondays or Fridays at the office, after work get togethers, weekend outings and holiday shenanigans.

Winter smart casual

topcoat (sold out) | chinos | boots | scarf | gloves

More importantly, it's nice and warm.

I mix up the colors, but the layers pretty much stay the same:

  • Chinos (usually the Aiden chinos)
  • Button up shirt (preferably something heavy like flannel)
  • Sweater (half zip, full zip, cardigan or merino wool v-neck)
  • Topcoat
  • Scarf / Gloves / etc.
  • Boots
  • Thick warm socks (like these)

Really digging these acorn colored chinos. They're a great way to break up the monotony of navy blue and khaki, and they go very well with the colors you already own (like grey, green and blue).

Also, wearing a flannel shirt adds noticeable warmth to your getup. Much better for winter than thin cotton button ups.

But staying warm without sacrificing style is all about layering. Here's how I layer:

Layer #1: Plaid flannel shirt

Plaid flannel shirt

Layer #2: Navy zip sweater

Navy blue zip sweater

Layer #3: Topcoat

Double layer topcoat

Layer #4: Scarf and gloves

Scarf and fingerless gloves

The scarf is an old Christmas gift (thanks, Aunt Jenna!). I think it's from Gap – nothing fancy – but it happens to match my chinos and coat perfectly. Plus it's soft and warm.

You don't need more than two or three scarves. Just make sure they're versatile, neutral colors like brown, grey, charcoal, navy, tan or black.

The fingerless gloves have pros and cons. One on hand, these gloves let you use your phone or grab your wallet without taking them off. On the other hand, your fingers do get cold.

If it's below thirty degrees, I opt for regular gloves.

Cold weather smart casual

Couple of important points about this getup:

First, the fit is spot on. That's because the shirt is made-to-measure (from Blank Label), the pants are rolled up, and the jacket has been tailored (sleeves shortened).

Second, everything was bought on sale. I rarely pay full retail for clothing, and neither should you! Buying clothes on sale makes it much easier to save extra cash for tailoring, which is crucial for shorter men.

What do you think about this outfit? Leave a comment below!

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  1. Yeah, The fingerless gloves. Hmm. Jury is still out on that. Overall, informative article. Totally new to me. Will come in handy when visiting relatives in the DC area and the folks further up north.

  2. Looking good Brock!

  3. I get down with fingerless gloves as well, I’m on my phone too much to have to be taking my gloves on/off the whole time.

  4. I know you mention that the topcoat is sold out, but I really like the way it looks. Can you share what brand/model, or where you bought it?

    • It’s the Banana Republic “double layer” topcoat (XS). Should be back next year, or you can check their factory store (recently opened online).

  5. Malaquias Alfaro says:

    You know what really throws off a lot of your outfits is your stance. Awesome fabrics, beautiful colors, well fitting clothes, but sometimes you just look incredibly stiff when you put your arms by your side. Great selections though!

  6. i’ve worn almost this exact outfit before and really liked it. my scarf was grey, my coat was double-breasted, and my boots were suede.

  7. i just picked up a single breasted pea coat from j crew in their sale for half price! screw layering – its so thick that i just wear it over a shirt (still need gloves and scarf to deal with 0 to 5*C weather though). love the top coat on you but any coat that comes below my ass makes me look too short (think its just cause my upper body is too broad). great blog – keep doing your thing bro!

  8. Peter Roy says:

    Nice outfit, Brock – I have done something similar this year but you carry it off better than me 🙂 In terms of the gloves, I don’t know whether you can get these in the states, but in the UK touch-screen gloves are available in a range of styles – I think they impregnate the fabric with with something, and it works very well – it gives me enough fine control to send short text messages et cetera.

    As an aside, I have a question for you – I have receding hair so I decided to take control and shave my head regularly for the last couple of years. That’s fine but it means I have to wear hats right through the winter – do you have any recommendations? I like wearing beanies for warmth but my wife thinks they sometimes look more like a swimming cap (!) and I agree that it can look a bit out of proportion. I get a bit stuck with other hat styles, and what does and doesn’t work, though. Any guidance would be appreciated.

  9. Hey Peter,

    Good question. Hats are tough because it depends on head size and shape. I would go to an outdoor store and try on a bunch of different styles. You might need something that doesn’t fit so closely to your head, like a trapper hat or newsboy cap.


    • Oh, and I have seen those touch screen gloves. Good to know that they work.

    • I think when I’m layered up I can look a bit “pin head” sometimes 🙂 I like the trapper hat idea, I’ll test that out. I’ve tried a Yorkshire flat cap and it looks okay but my ears pretty much froze off so I might save that for the Spring…

  10. I just found this blog and I love it already. That is a really good outfit, and i’m hoping to learn how to dress better.

    One question, I signed up for the newsletter but haven’t gotten the pdf for the 11 simple tricks. Could I get that re-sent?

  11. Brock, SOS.

    I recently got shot down by a girl in a bar. Not uncommon. But wait, there’s more.

    She said it was because I was wearing a scarf (insinuating I wasn’t manly, maybe?)

    Is there a line between stylish and looking a little bit feminine? Where is that line? Was that girl just dumb? I would love to see a post on this.

    Because, let’s be honest, dressing better is 95% about attraction/romance.

    • Malaquias Alfaro says:

      Your comment shows your intentions clearly. Dressing well and it’s reason varies from person to person as I dress well to be respected. Anyway, I’m glad you did make the remark in your comment as it helps us solve your problem! Yes unfortunately, scarves can make you look feminine. You have to be the right kind of guy. Maybe it was the way you had it tied? I was told the same thing once simply because I tried a new way of tying it. Sometimes scarves just don’t work for people. They only work for me occasionally. The whole line between feminine thing is tricky. This girl may have been dumb and wanted you to dress like every other “bro” out there or she may have genuinely disliked your scarf. You see, when you dress well you will be called metro. It’s almost guaranteed. But dressing starts to look feminine when you wear tight fitting clothing, not snug fit tight, and follow trends. That’s my take on it.

      Oh yeah I did want to make a comment on the scarf again, sometimes it doesn’t look feminine but immasculine. Like a skinny kid in PE, you may have presented yourself with too young of a look.

      • Dude… Thanks for chiming in. I definitely appreciate the in depth comment. Some of us don’t want to impress girls, some of us do, but we all want to look good.

        I don’t think dressing well has to be considered “metro” but I would love to see Brock write a post on the topic since he has thousands of readers and fans.

        • Malaquias Alfaro says:

          No problem. It sucks that people call us metro but that’s fine as we pass them up in life. Yeah, I’d love to see an article on this

    • Peter Roy says:

      Interesting comments all round – particularly about our motivations for dressing well. The first time I realised I wanted to dress better was actually a couple of months after I met my fiancee (now wife of 5 years). She dresses nicely, and I felt like I didn’t want to “let the side down” when we went out together – she had never said anything negative about the way I dressed, it was just something I decided for myself, and I’ve done so ever since.

      I think scarves can be a bit of minefield – I live in the north of England and it’s pretty conservative in some respects. Umbrellas are a no-no, for example – even if it’s raining on your head. You’re just supposed to get wet if you’re a “real man”. It’s that type of ridiculous ingrained logic that you’re fighting against.

      My parents have made fun of me a few times if I’ve worn scarves inside, and I think it’s because scarves in the UK are associated either with being ultra-posh, or part of the gay community depending on the type of scarf, how you wear it, and the general context. There is an in-between state where you can get away with it, I think, but you have to wear exactly the right scarf in exactly the right way; and if you don’t judge it just right people revert to stereotypes rather than try to understand it.

      My suggestion would be to consult with your female friends, and just does say outright, “Don’t be worried about hurting my feelings. Does this make me look X, Y, or Z?” If your purpose is to appeal to a broad cross section of women then really their opinions are the ones that matter; and that includes understanding the way they might prejudice or stereotype a guy wearing a scarf.

      • Malaquias Alfaro says:

        This comment was exactly what I was trying to say and simply couldn’t. I loved the minefield analogy and suggestion.

  12. Says the mailing list (for the special exclusive deals) is not currently active!

  13. Is the Navy Zip Sweater a sweater? or a jacket (Looks like a harrington jacket in the pic)? Its no longer in stock at BR.

  14. Hi Brock. I’d like to wear chinos instead of heavy jeans this winter. Chinos’ fabric are breathable and light though. Do you wear a thermal pant underneath your chinos?

  15. Brock do you wear a pea coat as well or you always wear a top coat?

  16. Brock, and everyone else for that matter, ever heard of full gloves for smartphone users? Highly suggest looking into them. You can type with them on an never take them off. They used to be kinda crappy a few years afo, but things have gotten better. J Crew sells a pretty classy pair for $98 in sizes small to XL. They’re leather and cashmere. You can find cheapo ones for as low as $7 though. They’ve saved my tiny hands from cold many days.

  17. Hi Brock. I have a question. How do you keep your pant’s hem from “hanging” along the collar pull tab of your boots? every time I bend the pant’s hem always slid inside the collar pull tab.

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