(This is a featured post in collaboration with eBay [#followitfindit] and Style Coalition.) 

Hey Gents,

As the temperature begins to dip here in Northern California, I’ve started thinking about some new garments I’d like to acquire in preparation for winter.

I haven’t made any cold-weather purchases in several years. My (now) wife bought me a navy peacoat four years ago, and I’ve worn it so much that I put huge holes in the lining of every pocket. (Needless to say, they must be repaired.) I have a bunch of flannel shirts, one or two pairs of leather gloves, and a pair of bean boots I bought two or three years ago.

Like I mentioned before, I don’t go shopping all that much.

Nevertheless, here are three items I’m considering buying from my Looking Sharp, Dressing Smart, Staying Warm Collection. At the end, I’d love to hear what three items you’re considering picking up for the winter.

1.) A sturdy, durable, handsome boot

Iron Range-Amber01Currently, I have one pair of LL Bean boots (sorta like these), and I want something similarly rugged and durable, but a bit more refined.

I’m considering Wolverine’s 1000 Mile, the Red Wing Iron Ranger, or the Jack from Danner Boots, a model I just recently discovered.

While the LL Bean boots have served me well the past four or five winters, I wanted to add another boot because 1.) they’re great for the colder weather, 2.) they add a bit of variety to my typical selection (as well as give my more summer-friendly loafers and boat shoes a rest), and 3.) I find the bean boots to be a little more casual than I’d like sometimes.

2.) A great wool hat

I bring a straw trilby with me when traveling to warmer locales. I wear it every single time. I want to carry that habit over into the colder months, and I’m exploring other hat styles I can pull off.

I’m considering a classic fedora from a brand like Stetson or Goorin Bros. It took me a while to get used to the fedora silhouette on my head, but the more I tried it on, the more I loved it.


A tip if you’re trying to incorporate new things (especially hats and sunglasses) into your wardrobe: it’s important to search for inspiration images, try on many different styles, and to get the opinion and help from an associate (assuming he knows what he’s talking about).

Inspiration images give you real life examples as to how you’d wear the item, and trying on many different styles will help you figure out what suits your face and head shape best.

In my case, I realized I can wear a fedora with a slightly shorter crown, but something like a porkpie doesn’t complement my head shape… at least in my opinion. The verdict is still out on bowlers and western cowboy-style hats 🙂

3.) A warm topcoat

topcoatAssuming you live in a region that experiences seasons, a topcoat is a great addition to your wardrobe. The key is to find one that looks as great with a suit as it does with denim and a sweater.

Here’s another one I like (although it’s black… I’d prefer charcoal).

My problem with overcoats is that I feel a bit like a midget in them. I’m 5’9″, but the longer length really throws me off. On the other hand, the topcoats I’ve found tend to hit somewhere between mid thigh and the knee, which I’m a bit more okay with.

Style tip (more like proportion tip): You never want your top half to appear longer or taller than your bottom half.

J.Crew is my brand for such coats, because they happen to fit me really well. As always, I encourage you to explore stores and find brands that fit you best. It makes shopping much, much easier.

And if you’re considering a versatile wool topcoat as well, look for something in navy, charcoal, or brown, with a subtle texture or pattern. If you go with the bolder, brighter checks, you lose a bit of versatility and formality.

Over To You

Check out some of the cold-weather items I’ve collected here, as well as my other Collections on eBay.

(By the way, eBay is giving away prizes between $1k and $25k, just for sharing some of your favorite Collections. It may be a long shot, but you never know. Plus, it’s as easy as hitting “share”. Curious? More details here.)

What are three items you’re adding to your wardrobe this winter? It’s okay if my winter is your summer (I’m talking to you, Southern Hemisphere readers); I’m still curious what you’ll be adding to your wardrobe during this seasonal change. Let’s hear it in the comments below.

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12 Responses

    • Barron on

      Dan, those are great! Thanks for sharing. Which colorway do you have? I don’t usually like black boots, but love that those have the natural-colored sole. So great.

    • Bo on

      Those boots look amazing! If I hadn’t just gotten a pair of Wolverine 1000 Mile Austen boots on a great discount, I would jump on those! Absolutely fantastic looks.

  1. Andy on

    About Fedoras: my advice would be to either go vintage or go custom. Check out The Penman Hat Co, in Oregon, or AdventureBilt Hats. If you buy a hat elsewhere and it has a feather in the band, remove the feather immediately.

    I recently picked up on eBay a large, double-breasted overcoat in a dark brown Zegna wool. I got it for a song as it had some moth damage. I had it altered and shortened slightly and the visible damage repaired. Now all I need is some colder weather to wear it.

    • Barron on

      Hi Andy, thanks for the tips and suggestions. Will check out those hat companies. Out of curiosity, why remove the feather? Is it because I didn’t find it myself?

      How much did those alterations cost for the Zegna coat?

  2. Guest on

    hello barron: i’ve had a terrific collection of fedoras, jeffs, walking caps and triblies but generally only wore them when i dressed up. i didn’t want to look like an old man, or worse – ironic! but now that i am an “old man” (61, but i still play rock and roll 🙂 i am considering wearing them on an (almost) daily basis. thanks for the encouragement. best, bob

    • Barron on

      Definitely, Bob! I’ve seen hats such as the ones you mentioned worn with various types of outfits, from dressy to casually. I say try it out, and the more you wear them, the more you’ll realize it can be done in numerous ways. More importantly, you’ll feel more comfortable doing so.

  3. Andrew on

    Dear Sir, first and formally I absolutely love EF, thank you for your excellent advise and commentary. Secondly this year I have chose to incorporate coats of velvet, scarves, and a hair style that is shortly cropped-as my hair is receding. I understand that the coats may sound eccentric, however, I have discovered that when found (as men’s velvet coats are rare, at least in my area of California), and tailored well, they become the admiration and talk of the room. Further, when these are coupled with a complimenting scarf, they allow one to easily transition from the most frivolous to formal affair-black tie excluded. Lastly, I have never worn a hat, but after reading your column I am both intrigued and excited at the prospect, and will explore the possibility and see what I find.
    Take Care,

    • Barron on

      A velvet coat does sound eccentric 🙂 I love a velvet blazer but haven’t seen many coats, and I imagine you’d have to be certain of the weather to wear one (as well as very confident in your personal style). That being said, if you find one you love, go for it!

  4. Kent Black on

    I was trying to decide between the Wolverine 1000 mile last year and the Alden Indy 405 boot. I went the Indy boot and am really glad i did. They look amazing with jeans, slacks, or just about anything. they are more than the 1000 mile but not a whole lot. The sole is also great (neoprene/cork) as it is not a leather sole and has performed great in the first Denver winter I have had them. http://www.aldenshop.com/Store/DrawProducts.aspx?CategoryID=163&ParentID=4&PageID=&Action=

    • Barron on

      I love the Indy boot. Been checking them out for the past couple seasons now but haven’t pulled the trigger 🙂 Should’ve included that in my list above. Great suggestion!

  5. Paul Abrahams on

    Well its winter here in Australia and 6 months later… I’ve bought 4 knits from woolovers.com A Lambswool Norwegian style Button top jumper in flannel with cream pattern, A Lambswool Zip (stand up collar) jumper in Navy, Aran heavy cable crew neck jumper in white, a cashmere and cotton polo knit in French Navy with Light blue collar and sleeve trim. . . some casual Brown Brogue boots I got on sale from ASOS. Fingerless gloves, a few thermal think pairs of socks. 4 scarves in various tartan colours. All under $300.