Ashley Tries Not Freezing in a Skirt

Every once in a while, I’ll get a question that pushes me to the limits of my outfit creativity.  This week I’ve tried to answer the question, “How can I wear a skirt without freezing to death in the winter?”

It actually wasn’t the best week to try to solve this problem, because (after a few days of very autumnal weather) it warmed up and got pretty toasty in the afternoons.  But I’m dedicated to answering your burning fashion questions, even when I’m burning like a fashion question.  I stuck with all my layered outfits until I got home from work and changed into something else that was less hot.  So without further ado, here are a few creative suggestions for how to keep warm while wearing a skirt!

Statement Tights

Tights and leggings are an obvious solution to coldness, but why stick to black or tan or bland tights?  Brighten up a neutral outfit with some bright tights.  Truth is, I wear this burgundy color so much during the fall and winter that I count burgundy as a neutral color.  It goes great with black, brown, gray, blues, greens, RED, pink….you get the idea.  I also have bright magenta tights and they really bring the party to a neutral outfit.

I wanted to show off the tights by making them the only colorful element in the outfit.  There’s a wonderful description in The Princess and the Hedge-Pig by E. Nesbit.  A king and queen decide to decorate a basement for a secret christening celebration and they must decide how to handle a conspicuous copper drain.  “Now this copper had been a great trial to the decorators.  If there is anything you don’t like about your house, you can either try to conceal it or ‘make a feature of it’.  And as concealment of the copper was impossible, it was decided to ‘make it a feature’ by covering it with green moss and planting a tree in it… It had been very much admired.”  This is also the case with clothes.  Conceal It or Make A Feature Of It.  Tights can easily fade into the background, but if you make a feature of them, fun tights can add a real kick to an outfit.


Another feature of the tights – they showed off the cool cutout detail on my shoes.  My feet are about the same color as the shoes, so they don’t provide enough color contrast to show off how cool the shoes are.  With a burgundy background, those shoes pop.  This outfit felt basic, but cool.  An oversize denim shirt dress, a long cream sweater with a zigzag pattern on the lapel, burgundy tights, and tan shoes.  I also think I wore bird earrings.  It was Monday and that was a long time ago and I’m honestly not sure.  I have a feeling that bird earrings were involved.

Guess what?  Monday Me knew that Saturday Me wouldn’t remember about the bird earrings, so Monday Me took a picture of them!  I know my memory resembles that of a sand flea, so I usually take that into consideration.  I do sometimes think, “Nah – I won’t write it down.  I can’t possibly forget THAT.”  Let me tell you, that never ends well.  Never.

Wear Pants

This one is might seem like cheating, but if you freeze whenever you wear a skirt, go ahead and wear pants.  Tuesday was a day with lots and lots of meetings and communications and businessy business things, so I wanted to feel like a boss.  I found this pantsuit at a thrift store for less than ten dollars, but it is still a suit.  And a suit signals confidence.  There are drawbacks to it – the jacket is oversized and the pants are pleated and high-waisted.  But once I belted the jacket, both those drawbacks faded into the background.  The bright red short-sleeved sweater under it really made it for me.

I got a lot of “nice suit” comments that day, usually accompanied by a huhI wonder what Ashley is doing kind of look.  I work in a tech department, so if a suit is worn, there must be a definite reason for the suit and it invites comment.  This applies equally to guys.  I’m the first to ask one of my coworkers, “WHY ARE YOU WEARING A SUIT?  DID SOMEBODY DIE?”  Just kidding.  But I definitely comment whenever anybody shows up to work in a suit.

The main problem was how hot I got in this suit.  I won’t wear this one again until there is snow on the ground.  I’m serious.  Way too hot.  But oh-so-fun to wear, because I walked tall in that suit.  And the whole oversize thing is very in right now, so I’m kind of on trend with this one.

Boots and Slips


Knee-high boots keep half of your legs warm.  For those of you who hate tights (and I know there are some of you), this is a good option.  I could also have worn a longer skirt, which would have kept the knee region warmer.

While we’re on the subject, not all skirts are created equal.  Some skirts will keep you warmer than others.  Longer lengths help, thicker material helps.  Stating the obvious, a wool skirt that comes down to mid-calf is going to keep you warmer than a linen skirt that hits above the knee.  The fit also changes the warmth.  A skirt that fits at the waistband and then goes out will allow free airflow all up and down your legs.  A straight skirt or a pencil skirt will at least provide a little insulation.

So I had the boots to make half my legs warm and I had a half slip on.  Slips actually help a lot.  Slips are unsung heroes.  They help with static.  And especially with layering, static gets REAL.  If you have on a slip, you don’t have to worry about how your skirt handles daylight.  Slips keep you a little bit warmer and every little bit helps.  If you don’t have a half slip, buy one.  Direct recommendation.

Dress Over Jeans (And A Sweater)


I wanted to revisit the Dress Over Jeans thing, because that was my very first Ashley Tries post.  These are great jeans to wear under dresses, because they are very slim fit – like leggings, but without so much stretch.  They even have a side zipper, so they don’t add bulk under the dress.  The dress is stretchy and flowy, the jeans were fitted and tailored.  A good partnership.

Not one to leave well enough alone, I thought, “What if I also wore a sweater under this dress?”  What was I thinking?  I’m now basically wearing an outfit under an outfit.  I was too busy thinking about other things, I guess.  Like how my birthday is coming up next week.  Or what to eat for breakfast.  Or how I need to clean my room.  Or whether I should brush my hair.  All of those things are flitting through my head at any given moment and occasionally my outfit reflects this lack of focus.

It wasn’t too bad, because it was a thin sweater, but I was overly hot by mid-morning.  Should have seen it coming, but I lose focus for one minute and I’m wearing two outfits at once…. That being said, I would wear a shirt under this dress.  Just not a sweater.  This is another outfit that will come back once there is snow on the ground.

Long Sweater and Boots


I really like these boots.  They remind me of spats and armor and Nausicaa.  They give me some steampunk vibes and I’m a big fan of that whole oeuvre.  The boots kept my calves covered and the long sweater kept my rear warm.  What more could I ask for, really?  Halfway through the day, I took off the sweater and I was in the short-sleeved dress and boots and I still liked the look.

If you wonder whether it’s okay to wear florals in the fall, I say go for it.  I wear my clothes all year round, just with different layers.  If you think of other solutions to this problem, comment with your solutions!  I love hearing from you.  If you have other questions for me to tackle, let me know.  I like having a fresh challenge.  Thanks for reading – I appreciate all of you.

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