Fashion Advice: Winter Outerwear

Fashion Advice: Winter Outerwear

I’ve got a question. Aside from my incredibly fashionable New York Yankees baseball jacket, I haven’t bought a single piece of outerwear since college. It’s finally starting to cool off around here, and I’m realizing that it’s about time I replaced some of the old stuff hanging in the closet. I work in a shirt-and-tie office, but occasionally wear a suit to meet with clients. I also want to look professional, but relaxed, when I’m not on the clock. What would you suggest as essentials for the cooler fall and spring weather, as well as the freezing cold I can expect for a few months in the winter?

Fashion Advice: Winter Outerwear

Cary Cahill, Albany, NY


Thank you for the question. Like most of the fashion questions I get there is no one best answer. But to simplify things I can tell you I have found the black blazer either with silver or sometimes black solid buttons to be the best all around dressy coat to have.

– As far as dressing up goes it goes with all the trouser combinations of a navy blazer but has a more fashionable, younger feel to it. It works with tan, taupe & light olive slacks as well as light, medium and dark grey slacks.
– You can wear it with a tie or without.
– When without a tie, it can be combined with a solid, stripe or check dress shirt; with a sport shirt; or with a knit such as a polo, crew or mock neck sweater.

– A black blazer can often be put together with a nice pair of jeans. Again with a dress, sport, knit, but here you can also throw in a tee shirt.

When I wear a black blazer I always wear sleek looking black dress shoes, although another cool casual shoe might work as well. Even when I match it with a tan slack I still avoid brown shoes.

Unfortunately a black blazer is not meant to keep you feeling warm & cozy. It’s job is to keep you looking polished & professional. You might want to also add a ¾ length car coat for your more casual appearances. Usually these are cut with a straight bottom & a 90 degree corner instead of rounded like dress coat. They can sometimes be bought with a zip out lining to get you through a wider range of weather. Charcoal is a good all around color because it goes with earth tones as well as black & navy. A coat like this can easily go out on the town casually or to a not too dressy event.

When the really cold weather hits you may need an overcoat. When it comes to these there is nothing like the feel of pure cashmere. Cashmere usually starts around $1000 & heads up into the $4000-$5000 range before tapering off. Wool & wool blends work just as well & some are very soft. You can expect pricing to start at $300 & move up steadily to ten times that. Again they can be found with a zip out lining, but for me that is usually over the top and unbearably warm to wear. Of course we don’t get the cold spells in Seattle that hit New York every year.

Then the weather gets wet an overcoat should be replaced by a rain coat. Your options are full length, knee length & a version of the car coat that will come down to cover the seat. I paid $325 for my full length rain coat with a zip out lining.

Layering can help fend off the cooler weather as well. When it comes to scarves I have to have cashmere as wool is too itchy for such a sensitive area. Last year I invested in a scarf with black on one side & charcoal on the other. The great thing about them is they look great when combined with jeans or an overcoat. You can’t go wrong.

You can also accessorize with gloves & a cap. I wear leather gloves with faux rabbits fur. I prefer extra large so the fingers are long enough. Try on gloves & bend your fingers to see where the knuckles end up. For a cap I prefer a loosely banded knit that won’t mess my hair up too much. Usually if you have longer hair this can mess things up a bit. With shorter hair it’s not usually an issue.

One last idea for layering is the sweater. Argyle is very popular now but if you can’t handle the pattern go for a solid in a polo or V-neck. Put it on top of your shirt & tie. It can be a rather dashing look under a suit, sport coat or simply with slacks.

My Best,

Jeff Collins

Professional Haberdasher

p.s. Your Yankees jacket certainly has its place but not likely with a shirt and tie (perhaps baseball themed would work?).

Jeff Collins answers your fashion questions every month. Got a question for Jeff? Send it in to

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