A reader left a comment on an outfit post this past December — an outfit in which I wore an overcoat, ankle pants, and ballet flats, seen here — about wearing ankle pants in cold weather and asking for tips and strategies:
Thank you, teatimechic, for asking the question! I’ve been mulling it over for quite some time. It doesn’t get too cold here in the PNW (rainy, yes, but not that cold), so I’m generally ok wearing ankle pants with flats and/or with trouser socks. Bu I took a look back through my outfit archives to compile different ways I’ve styled ankle pants in cold weather — plus a couple of bonus ways I’ve seen other style bloggers style ankle pants in colder climes.
#1, with tall boots
This was the first way I thought of wearing ankle pants when it’s cold outside. This is also the warmest way to wear ankle pants in cold weather, to layer the pants under tall boots or tall rain boots. This works best with ankle pants that have slim or skinny cuts.
And my trick when tucking ankle pants into tall boots is to first secure the pant legs under longer socks. Even thin socks will do, as long as they’re long enough to cover the tops of the ankle pants. This will ensure that the ankle pants stay down and don’t balloon out too much around the knees, plus it ensures that your tall boots go on smoothly over the ankle pants.
Here are a few examples of how I’ve worn ankle pants with tall boots:
left (burgundy ankle pants) // middle (black ankle pants) // right (navy ankle pants)
#2, with ankle boots
Ankle pants with ankle boots — a match made in alliteration, yes? 😉 Ankle boots cover most of the foot and ankle, so it’s another decently warm alternative if you dare to wear ankle pants in colder weather.
Both examples below are with my olive ankle pants paired with my grey ankle boots.
left // right
#3, with menswear-style shoes
Of course, if it’s not too cold out, you can always wear ankle pants with flats or wedges — but I’ve found menswear-style shoes, like Oxford or brogues, to be a more modern alternative. Plus, this shoe style provides more coverage (and thus, warmth) for the foot and ankle. I wear low-cut ankle socks when I wear my brogues, so my toes are still toasty.
#4, with patterned socks
My blogger friend and SIA co-host Salazar @ 14 Shades of Grey has been rocking patterned socks with ankle pants/jeans and flat shoes this winter, as seen here, here, and here, for starters. This style looks good with either menswear-style shoes or ankle boots, and it definitely helps showcase your personality while also keeping your ankles warmer in the winter. Win-win!
Photo used with permission from Salazar @ 14 Shades of Grey
#5, with snow boots
For those of you in legit snowy climates — or those who have been suffering in unseasonably frozen temps in parts of the U.S. this past winter — looking at pics of bloggers wearing ankle pants and shoes with no socks looks kind of laughable. I get it. I know I’m lucky to live in a relatively seasonably mild (albeit rainy) region. So I appreciated reading style blogger Cori Lynn’s recent post about “things that actually work, when getting dressed in the winter.” Cori Lynn used to live in Seattle but has since moved to Connecticut, and she recommends snow boots with slim-cut pants or jeans! Visit her blog, Dress Cori Lynn, for more pics and tips for dressing for legit snowy weather.
Have you worn ankle pants in colder weather? If so, have you worn them these ways pictured here in this post — or another way altogether? Please leave a comment and share!
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