If you haven’t noticed, we here at The Gloss have been struggling to clothe ourselves lately. The temperature is dropping in NYC, and for the most part (screw you California), the rest of the country, and at least for me it feels like winter comes around every year and I am never prepared for it. How did I do this last year?? I ask myself while throwing ill-conceived cropped sweater purchases around my room. What on earth did I wear? Was it really this cold? I don’t remember it being this cold.

(Related: 6 Chic Work Outfit Ideas For When It’s Freezing Out)

My theory is that each Spring the ice melts, floral patterns emerge (and I guess actual flowers, whatever), and my mind completely blocks out all the memories of winter. But now that we’re back in the thick of it, I’m feeling lost all over again. But I refuse to sacrifice style for the sake of not getting hypothermia. And perhaps more importantly, I refuse to ignore my entire collection of skirts until Spring. It is with that last stubborn premise in mind that I embark on this outfit-planning journey. Hopefully it will inspire you and me both.

1. Midi Skirt with Tall Boots winter skirt outfit idea 1

As Heather said, a midi skirt in a heavy weight fabric (Structured Pleated Midi Skirt, Choies) is a must for winter. You can definitely wear them with tall boots, as long as they are fitted and preferably have a heel to lengthen out the look (Friggid Tall Boots, Nine West, on sale for $70!). And as much as I never thought I would promote anything from Abercrombie again, these fleece-lined tights are an absolute necessity. Top it with a cute basic sweater (Peter Pan Collar Sweater, Tory Burch), a bright wool coat (Boiled Wool Walker Coat, Land’s End) and cute earrings (Dainty Crystal Studs, J.Crew), and you’re ready to take on the tundra!

2. Skirt Over Denimwinter skirt outfit ideas skirt over pantsI know I know, just hear me out. This outfit was inspired by style blogger Rachelle Yade, who knows how to rock a skirt over jeans like no one I’ve ever seen. She is living proof that this can be a very cool look if done correctly. It can also be a way to wear your light denim in the winter (which I usually don’t do)! Start with a flowy midi (Zip Through Midi Skirt, Whistles), and layer over a pair of skinnies (Super Skinny Jeans, H&M) and a cute button-down (Striped Blouse, Mango). I was really feeling the many shades of blue vibe when putting this together. Add some pointy-toed boots (Gabba Boots, Aldo, on sale for $70!), a boxy jacket (H&M Boucle Coat), and a pop of color (Pink Petal Crystal Necklace, La Bella) to complete the look.

3. Leather Pencil Skirt

leather pencil skirt outfit winterInvesting in a tight leather pencil skirt actually pays dividends in the cold winter months. I would wear this look even without tights, but of course you could add them and switch these shoes for a close-toed version. The star is, of course, the leather pencil skirt (Viyella Leather Pencil Skirt, John Lewis), paired with a simple blouse (Silk Blouse, Uniqlo) and ankle boots that yes, are open-toed, but are still fairly warm (Suede Open-Toes Ankle Boots, Burberry). I add leather gloves (Agnelle Celia Leather Gloves, Matches Fashion), a wool jacket (Wool-Blend Straight Cut Coat, Mango), a chunky gold necklace (Knotted Statement Necklace, River Island), and faux fur earmuffs (Ted Baker Faux Fur Earmuffs, House of Fraser) for extra warmth!

4. Winter Maxi Skirt

winter maxi skirt look cold weather

It doesn’t make any sense that maxi skirts (Alaino Maxi Skirt, L.K. Bennett) should be almost exclusively a summer thing. They have the potential to be the warmest of all our skirt options! Not to mention you can wear anything you want underneath, like tights (Falk Cotton Tights, Avenue 32and warm knee socks (Cable Knit Knee Socks, H&Mand boots (Black Short Boots, Yoins). Add a turtleneck sweater (Grey Mohair Cowl Neck Sweater, River Island), wool coat (J. Crew Collection Tweed Wool Coat, Net-A-Porter), and ear muffs (Ted Baker Faux Fur Earmuffs, House of Fraser) for maximum warmth. Oh and cute studs (Kate Spade Bow Studs, Shopbop), just for fun.

5. A Mini and Over-The-Knee Bootsmini skirt over the kneeThis is actually a classic Rachel Berry post-sexy-makeover look, and I love it. Pair a wool mini (Atto Mini Skirt, The Corner) with a tight turtleneck sweater (Ella Sparkle Crop Turtleneck, Whistles) and over-the-knee boots (Diba Office Dixie Boot, DSW) for a look that will make you break out of your sweatpants and baggy sweaters and feel sexy in the winter months. I added the cape (Grey Tartan Blanket Cape, River Island) for some variety, but you can always add a more legitimate coat on top of that. For accessories I went with yet another pair of studs (Michael Kors Pave Studs, Saks Fifth Avenue)—I never like to wear dangly earrings when I’m going to be wearing a hat or earmuffs—and fur lined gloves (Faux Fur Cuff Gloves, Barneys).