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Transitioning my Caribbean Style to Fall/Winter

Until now, my winters have been spent in Toronto and London respectively; at the homes of family members, and their packed closets. So single digit celcius for me so far, has meant looking like a mini version of either my aunt or my cousin. I haven’t gotten much practice dressing myself as myself in the cold, because usually I opt to travel only to hot climates. I prefer a bikini over boots any day. I is a Trini.

This time around I have found myself in Nueva York in the middle of Fall. My prayers were working fine for a while, with mid-October still warm enough for short pants. Then this morning I wake up and can’t feel my face. I knew it was coming. (Good thing I bust outta here in a few days!) So what do I wear? This has honestly been stressing me! My style is usually made up of convertible, simple pieces with cool, unique accents here and there. I like things that are slightly androgynous, I like oversized tops and ankle length bottoms.  I love yellow and warm brights and denim. Lots of denim. The coats I’ve been seeing in stores…. gross.


I went on a shopping trip with my roommate and fellow stylist Merideth Morgan, as well as with model Elly Mayday (pays to have stylists and models as friends when you wanna look fly). While they were trying on stuff that looked great on them, and more importantly that looked like them, there I was staring blankly at 100 types of boots, wondering which one of them was my signature. I ended up getting two pairs of knee high faux suede ones; one in grey and one in navy, and I can imagine myself in them with cool tights and men shirts. Will I be warm? Probably not, because if you ask Merideth, I need one of those Michelin man looking puffy jackets to be warm, and I am just not mentally there yet.

I must have tried on 10 different coat styles, leading me to find out that Number 1, I am a very tiny human, and 2, That if I don’t look like a Sesame Street character, I am not into it. I have a blue fuzzy jacket that strongly resembles Cookie Monster. And on this trip with the girls, I was only drawn to a Big Bird yellow Pea coat and this red Elmo inspired fuzz ball. Elmo is the only jacket that allowed me to visualise myself in it, so I took it home.  Oversized, cropped length and covered in faux fur stars? Okay, now we’re talking.

Earrings by Cocoa Vintage, Shorts by Sheneice James, Elmo Coat by Belle Vere

So far what I’m liking for Fall are brightly coloured faux fur jackets. This rose gold coloured fluffy hoodie is a surpising colour choice for me, but I really love it. I love it so much  might even get sneakers to match. Coloured, fishnet or patterned leggings are also a “Do” for me. We already know I am obsessed with the sparkly variety of panty hose.

They look great, but the embellishments rub between boot and leg and well, ouch. | Starry Nights Fishnet from Lirika Matoshi

I guess to stay true to my personal interpretation of Caribbean style, colour and mixing texture is essential. So I am finding that appearing like a plush toy on glittery stilts may be my look. Boots I find particularly comfortable so I’m not hating on that. Style wise, I feel I am a combat boot-wearer of sorts, but my  foot is a size 6, and I’m guessing the thought process in boot-making is that children (i.e. People of my stature and foot size) do not need combat boots. I’ll keep looking.

A friend answered my cry for help via IG post, and suggested fleece-lined leggings. Is that a thing? It sounds amazing. Someone else suggested hats. Now, this is hard for me. I wore a beanie in London two winters ago, and I did enjoy it with my newly chopped bob, but I need to try it out with this wild head of balayaged curls. I was gifted a J.Lo- esque hat that is super chic, but the rest of me usually looks like a tomboy in heels, so I am not yet sure how I would style it. Hats give me anxiety. I go from cool Indian girl to Doubles woman very fast.

We’ll see how it all goes. I’m enjoying bombers, and Camouflage print- anything military inspired actually, patches, pockets, heavy shoes- My style so far is looking like it’s a muppet militant. Could that be the next big look for fashion?

I’m wearing a Sheneice James Body suit under here. Yes, It is more like a felt swimsuit. Now that is Caribbean winter style if there ever was a Caribbean winter.



Pictures taken by Merideth Morgan, Looks styled by Me




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