Three Ways I’m Keeping Warm, Dressing Smart, and Looking Sharp This Winter

November 14, 2013 · 12 comments

in Feature, Outerwear, Shoes

(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.


Barron is the founder and editor of Effortless Gent, a site dedicated to helping guys figure out what looks best on them. He's based in San Francisco. Connect with him on Twitter and Facebook.

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