Skirts dominate my closet—I’d argue they’re my favourite trend piece to model. Skirts with boots, colourful skirts, skirts with sweaters… the probabilities are infinite! Recently, I’ve been interested by how skirts are likely to shine for most individuals in spring and summer season, however are sometimes ignored with regards to fall and winter dressing. Let’s change that! Right this moment, I’m sharing a few of my favourite skirt outfit concepts for cooler temps in addition to current kinds which have caught my eye. Let the layering start!
How you can Put on Skirts within the Fall and Winter
Earlier than diving into my skirt outfit concepts, let’s chat about how you can make these items work through the cooler months. After dwelling in NYC for years, I picked up a number of styling methods that make it completely attainable to rock a skirt—even when the temperatures drop.
Information Flash…You Don’t Must Be Chilly
I feel many individuals draw back from skirts when cooler climate rolls in as a result of, understandably, they don’t need to be chilly or uncomfortable. However once you get artistic, skirts can really be fairly heat. I really like layering tights beneath (generally even a number of pairs), pairing skirts with boots and tall socks, and infrequently sporting heat-tech biker shorts beneath for additional heat.
Combine and Match Lengths
I all the time love taking part in with proportions, and skirts are excellent for this! For instance, I typically pair a mini with an extended coat or duster. This combo is each useful and trendy all of sudden—and considered one of my favourite skirt outfit concepts for fall. Relating to pencil skirts or high-waisted midis, strive a chunky, cropped coat to create steadiness and visible curiosity. Mixing and matching lengths helps outline your form and create a flattering silhouette, and the layers of fall and winter make this much more achievable.
At all times Decorate
Don’t draw back from belts, fake fur stoles, or gloves when styling a skirt for fall and winter. Equipment are an effective way to introduce new textures, add a little bit of shade blocking, and naturally, keep heat!
Skirt Outfit Concepts for Fall and Winter
Now that I’ve shared a number of ideas for pulling off these appears through the cooler months, let’s dive into some skirt outfit concepts. Listed below are a number of of my favourite methods to model them fashionably whereas staying heat and comfy!
1. Mini Skirt + Layered Coat
This combo needs to be considered one of my favourite methods to model a mini for fall. Pairing it with a thicker coat is easy—and there are such a lot of methods to make it your personal.
For instance, strive styling a classy mini with a blazer cinched on the waist with a belt for added construction. Add tall boots and a second layer of outerwear, and also you’re good to go! This traditional fall outfit is a superb instance of a glance that’s each polished and sensible.
If it isn’t too frigid out but, one other nice transitional choice is a mini skirt paired with sneakers and an extended coat layered on high. I just lately styled this look with various shades of inexperienced and a mixture of supplies and textures to maintain issues fascinating.
Lastly, you may skip the boots and as a substitute layer socks and tights collectively, as I did with this turtleneck outfit. I really like how the outsized barn coat lets the mini simply barely peek out—it’s such a enjoyable proportion play for fall!
2. Fall Midi Skirt
I’ve really written a complete submit on how you can model a midi skirt because it’s considered one of my all-time favourite silhouettes. That submit contains loads of skirt outfit concepts, however listed below are a number of methods I wish to model these items particularly for cooler climate.
For a fall, dressed-up on a regular basis look, I really like pairing midi skirts with a chunky sweater and flats. This printed midi and sweater outfit I wore in Paris is a superb instance of that mixture.
For those who’re trying to transition your midi skirt for a extra party-ready vibe, strive pairing it with a peplum high and platforms, as I did right here. One other elegant choice is styling a midi with a traditional tucked-in shirt and stilettos.
And whereas the midi skirt is inherently a female form, don’t be afraid to combine it with extra masculine footwear. I just lately styled a midi skirt with Western boots and once more with loafers and socks — each appears turned out fantastically! It’s all about experimenting and layering to see what works for you.
3. Celebration-Prepared Skirt Outfit Concepts
With the vacation season proper across the nook, it’s the proper time to begin planning skirt outfits that may take you from cocktail events to festive dinners. There are such a lot of enjoyable kinds to select from proper now!
Wrap Maxi Skirt
One among my favourite trending skirt kinds is the wrap maxi. It’s subtle, simple to put on, and such a flattering form.
I just lately wore this wrap maxi skirt outfit for the Tuckernuck retailer opening in September. Because it has an attention grabbing tie waist, I opted for a easy tucked-in high. So as to add a bit of heat—with out competing with the bow—I merely draped a sweater over my shoulders.
Pencil Skirt

One other party-ready choice is the pencil skirt. I all the time really feel a bit of dangerous for this model, since so many ladies solely affiliate it with workwear. However right here, right here, and listed below are a number of nice examples of how this silhouette can celebration!
This mixed-print look could be excellent for a fall cocktail celebration—I really like the way it turned out!
For a extra overt celebration look, strive a fluted pencil skirt outfit. Want a bit extra protection? Pair it with a turtleneck bodysuit or add a fur stole, like I did for a winter celebration final 12 months.
Waterfall Waist Skirt

One other enjoyable, surprising selection is a colourful waterfall-waist skirt. This distinctive silhouette immediately turns into the star of the present—no additional styling required!
My Private Present Favourite Skirt Outfit Concepts
Now that we’ve lined some fall and winter skirt outfit concepts, let’s take a peek at a number of of my present favourite kinds for pulling off these appears. As you understand, I’ll all the time have my eye on a fantastic full midi skirt or a preppy pleated mini—however under are a few of the trendier choices I’m searching for this season!

Sheer Pencil Skirt
One among my favourite trending items for 2025 is the sheer pencil skirt. Is it a midi? A mini? It’s a bit of little bit of each! I’m at present eyeing this one and this one.
Satin and Lace Skirt
Satin is actually having a second—from slip attire to slinky skirts, the fabric is in every single place. Two very fairly choices on my wishlist proper now are this silk-and-lace midi and this burgundy skirt. Each would look beautiful styled with an outsized fisherman sweater and smooth flats.
Leather-based-Like Mini Skirt
And let’s not overlook a couple of leather-like mini! That is one other skirt at present on my wishlist, and I’m loving all the pieces from croc-embossed kinds to smooth, minimalist items. My checklist retains rising—however this one, this one, this one, and this one are at present on the high!
Celebration Pencil Skirts
As I mentioned above pencil skirts should have some enjoyable too! There are A LOT of fine choices this season. Private favorites embody this printed one, this excessive sequin model, and this chartreuse choice. If cash had been no object I’d be scooping up this one and this one. A lady can dream!
Skirt Outfit Concepts to Attempt This Fall and Winter
As we head into fall and winter, I hope these skirt outfit concepts encourage you to succeed in for a skirt—it doesn’t matter what the climate is perhaps. In any case, we will’t let a bit of temperature drop cease us from sporting what our coronary heart needs, can we?
For those who love traditional, wearable, and enjoyable outfit inspiration, you’ll want to try my posts on how you can model loafers and denims, colours to put on this fall, 4 kinds of boots to put on with denims, and how you can model a fisherman sweater.


