Cold Weather Outfits For All Seasons

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When I think of winter in the Southern states, I think of thermal indecision. I think of freezing cold mornings followed by spring-like warm afternoons, or blazing hot days followed by weeks of rain and finally, if my sacrifices to the weather gods have worked, a perfectly cold day or two. Ten years of living in a subtropical climate and I’m still not sure how sharply the weather might change from one moment to the next. Alas, as we have our entire lives, one must dress with the information at hand.

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As for life, that important thing, weather be damned, winter has consistently involved work during the day, peppered with trips to chiropractors and mid-day runs to the studio or the post office or other fascinatingly quotidian places. However, one beauty of Southern living I’ve embraced since the very beginning is that you don’t need an occasion to have some fun. Brunch is a regular ritual, followed by museum trips or wandering our favorite book shops, and a mid-week evening is just a good a time as any other to have an elaborately (or not) planned night out with friends. Winter is grey and depressing, and the only way through is to make getting out of bed worth it.

The school girl has grown up and is now your favorite art history professor at the local liberal arts university.

December and January, and even February, have always had their own interesting effect on my personal style. While I embrace every ounce of the feminine in the warmer, brighter months, and even cling to it again around Christmas, New Year’s, and Valentine’s — those wonderful reasons to wear the most voluminous of skirts and sparkliest of dresses — something clicks in me around late autumn and suddenly my entire wardrobe becomes full of dark, menswear inspired basics by the peak of winter. Maybe I just like a tailored uniform, maybe I like to be my own boyfriend sometimes, but for whatever reason, my inner dapper prep school girl lives in the winter months.

In the last few years, said prep has become more louche and luxe, gravitating toward a softer silhouette with more oversized than fitted knits, wide leg trousers so soft they could pass off as pajamas, and a still dark, but warmer color scheme. The school girl has grown up and is now your favorite art history professor at the local liberal arts university. Day to day outfits are easy enough to work from home in, but suitable enough to run out in should the occasion arise.

Sandals, Steve Madden. Similar    here   .

Sandals, Steve Madden. Similar here.

Vintage Custom Slip, GAP blouse. Similar styles    here    and    here   .

Vintage Custom Slip, GAP blouse. Similar styles here and here.

I’ve been living in a pair of black linen high waist, wide leg trousers almost all season, originally from Old Navy. They serve me well in warmer weather but are comfortable enough that I can wear them through the colder months over tights or leggings. I’m only 5’3, but have a long enough torso that I’ll buy bottoms in a tall when I can find them for a better rise. I’ve also taken in the waist and altered the length. I’ll never thank my mother enough for teaching me how to sew as a child, leading to a life in fashion but also for the joy that comes from being able to make my clothes whatever I want them to be.

On my laziest days, I’ll throw a stolen men’s button down or vintage-inspired flannel over or under a slip. A proper black slip goes without saying; I’ve got at least three and wear them on their own or under other dresses for extra warmth.

My goal most days, but especially in cold weather, is to essentially never feel like I’m not in pajamas and these pieces make it so.
Vintage pullover, J. Crew Collection. Similar    here   .

Vintage pullover, J. Crew Collection. Similar here.

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Cropped but slouchy knits make for good moods, and my favorite is this perfectly camel, dolman sleeve cashmere number. Tucked into trousers for business or a-line mini skirts whenever I feel like a 60s ingenue, it is several years old and moth ridden but I’ll love it forever, just like the friend who gifted it to me.

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I think fine (as in stitch size and yarn weight), short sleeve knits are the greatest creation we don’t talk about enough. Cozier than a silk blouse and a step above basic tee shirts, I live in these year round and pair them with everything from skirts in the early days of spring to slouchy velvet trousers when visiting my chiropractor. Another favorite chiropractor look is a soft velvet tee and some printed easy trouser. My goal most days, but especially in cold weather, is to essentially never feel like I’m not in pajamas and these pieces make it so.

Velvet Tee, GAP. Similar    here   .

Velvet Tee, GAP. Similar here.

Custom Trousers.

Custom Trousers.


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I don’t accessorize a lot because jewelry can get in the way of working with my hands. I like freedom of movement whether I’m sewing at a machine or bent over a drafting table, and having to push a long necklace or bracelet away can get tedious. I think back to my favorite sewing professor who wore very little outside of her watch and a good silk neckerchief. The woman is a style icon. I’ll compensate the lack of sparkle in other areas, be it an interesting silk scarf of my own (mainly used to keep my hair out the way — hair ties and topknots lead to migraines for me) or interesting footwear. When in doubt, I’ll reach for a suede or velvet smoking slipper but I’ve also been loving the faux fur slides that have been trendy of late.

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Faux Shearling Coat, Old Navy. Similar    here   .

Faux Shearling Coat, Old Navy. Similar here.

Evenings with friends or days off running errands usually bring out actual winter wear, as leaving the house requires not only coats but also tights and boots. I love ankle boots with everything, and live for statement coats, so I tend to formulate outfits around those pieces first. As I’ve been quite literally living in this cream faux fur coat (I even slept in it one chilly night because I was too tired to turn on the radiator), the formula for it has become pretty straightforward —  slinky midi length rompers and dresses and low heeled ankle boots like they’re going out of style. An enormous pink J. Crew find was an end of January steal, marked down so much that buying it felt like I was getting away with something. My only purchase all season, I’ve been wanting a brightly colored coat for years and will be wearing this one every last chance I get, as well as in the years to come.

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As the season comes to a close and I think of the next in-between temperature to hit, I know I’ll probably carry a fair share of these pieces into early spring, but start bringing back some of the lighter colors and swingier shapes that remind me of springtime. Boots will become oxford flats and slippers will become sandals, large pullovers will become boyfriend cardigans over floral prints. Flowers in bloom, light breezes on perfectly warm days, outdoor brunches... I can’t wait.

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Raquel Reyes is Creative Director at The Attic on Eighth. She enjoys styling photo shoots, dramatic hair accessories, and old fashioned cocktails.


All pictured clothes and accessories belong to the author. Similar styles have been linked where mentioned items are no longer available. No material in this post is sponsored, but we use affiliate links and may earn a small commission to help in the running of this site at no additional cost to you.