Can you believe Thanksgiving is around the corner? I’m excited to see family over the next two months, and honestly, I’m already thinking about Thanksgiving leftovers. Anyway, let’s talk skirts that you can wear with sweaters! There are lots of outfits for different occasions and styles, whether you’re going to a holiday party or looking for something to wear to work.
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I’ve always gravitated towards midi skirts for work, but I love them for casual wear or a date night look too. The options are endless when it comes to pairing a sweater with any length skirt during the cold months. They’re an iconic pairing and a classic combination this time of the year. You’ll feel put together, and you’ll still be warm! So, let’s get into sweater and skirt outfits that you can add to your wardrobe rotation. As always, I include pieces I hope you can mix and match with other things in your closet too.
Fifteen Sweater and Skirt Outfits for Work, Date Night, and Everything Else
Sweater Skirt and Matching Sweater Outfit
This has been a go-to outfit for me for fall and winter since I bought it last year. The skirt is thick and warm, which means it doesn’t show any undergarment outlines. This outfit is perfect for a date night, dinner out, or a holiday gathering with friends. It would also look nice with this denim jacket to dress it down. Denim is the perfect fabric to turn to when you want to make your outfit feel more casual.
Shop my outfit here. There are also other solid color options!
Embellished Skirt with a Blazer for Holiday Parties
I saw this ruffled flower skirt, and I was instantly transported back to my early 20s when I would never miss a holiday party. This is the exact outfit I would’ve picked, and I’d still wear it today. Even fun looks can be classic! I love to pair a blazer with anything, and it gives a cool girl contrast to this super girly skirt. You can wear the blazer on, drape it on your shoulders, or just leave it at the door once you’re at the party.
I love blazers because they create a long line to help you look taller, and they also help take attention away from your midsection if that’s one of your goals. Okay, if I’m being true to my 20’s self, I definitely would not wear tights, but I’d wear knee high or over the knee boots. These days, I’d go for the same shoe and a pair of tights!
I’ve been eyeing these boots for two years now, and this is the perfect outfit to wear with them. You definitely don’t need to be on the holiday party circuit to wear these! I love that you can also wear them with super casual looks. You could also style this skirt with a black cashmere sweater and black over the knee boots – I own both of these items and love them. These black suede boots are perfect if you’re facing any inclement weather because they’re waterproof.
Cozy Sweater Skirt and Matching Sweater
I love this matching cashmere sweater skirt and sweater for every day wear. It’s cashmere, so you’re going to be warm and comfortable. You can dress it up with boots for a night out or wear it with sneakers during the day. The skirt and sweater both work as separates to make other outfits, too. I would definitely wear this sweater with jeans, and you can wear the skirt with a blazer or a denim jacket.
However you style it, this outfit will look stunning with a necklace and bracelets. This is the type of jewelry you can wear every day. But, they still work to dress up an outfit if you’re going out for a date or to a party.
Mini Skirt and Sweater for A Night Out
This faux leather mini skirt is the perfect on-trend color for fall and winter. I love that it’s not as serious as a black leather skirt! It will look so cute with this oversized sweater for a fun night out with your friends or significant other. Wear the sweater untucked over your skirt. I saw this sweater in store, and it’s perfectly oversized to balance out a mini skirt. You can definitely wear the sweater with jeans and other skirts too. I linked a pair of boots and brown tights I would wear to complete the look.
Denim Jacket With Corduroy Collar And Black Cotton Maxi Skirt To Wear Anywhere
A sleeveless cashmere sweater or a sleeveless wool sweater is one of the most versatile pieces you can have in your closet. It’s so easy to layer, and you can wear it a lot without needing to dry clean it. I typically only need to dry clean mine once or twice a season. This dark denim jacket with a corduroy collar is also perfect for fall and winter. I love that it’s 100 percent cotton. It will hit at the perfect length to wear with a maxi skirt. I own and love the one below. I wear a 6 petite in it for my 5’4 height, but if you’re 5’4 and above, you can definitely get away with the regular length if you wear a boot with pretty much any heel. Shop petite here and regular here.
Midi Skirt with Sweater for Work
If you’re looking for an outfit that you can wear a lot for work through the fall, winter, and spring, look at this option. You can wear this outfit as it is, or you can treat it as a base outfit and add different layers or accessories. If you want to wear this for a casual Friday, add a denim jacket! If you want to spruce it up for a meeting, add a blazer and a belt!
Suede Jacket With Cotton Skirt
If you live in an area where you don’t need a heavy jacket, or you’re looking for something to wear in the fall or spring, this outfit is the perfect option! I have this skirt in black, and I love it! If you carry any weight in your midsection like I do, this a-line skirt is super flattering. I styled this with sneakers, but you can also wear this with boots, ballet flats, or loafers. That’s the nice thing about this skirt – it’s really versatile! I wear it throughout the summer too.
Link Print Blouse And Slip Skirt With Seam Detail
The link print on this blouse is so pretty – it jumped out at to me! I styled it with a similar material skirt, but it would also look beautiful against a knit skirt to add some texture to your look. This knit skirt is perfect if you want to wear this outfit outside of work. If you want to drape a sweater over your shoulders that would look cute with this outfit, but I don’t really find that to ever be practical, ha! So, if you want to add a layer of warmth, you could layer this blouse under this black cashmere vest so you can still see the beautiful print!
Monochrome Skirt and Sweater Power Outfit
If you have any days at work where you’re doing a presentation or any other public speaking, then this is the skirt! It’s gorgeous. You could also wear this to a special event or during the holiday season. The silk blouse adds a delicate detail to the outfit so it doesn’t feel too heavy! You could easily layer this with a lady jacket or wear it with this brown cashmere sweater if you want to be super cozy (but still professional).
This bag has been on my wishlist forever. I love this take on a classic briefcase. I remember when I first moved to London, I absolutely loved seeing all of the satchels that women were carrying! I always wanted one from Cambridge Satchel.
Slip Skirt and Cozy Sweater for Christmas Shopping
This slip skirt and sweater are meant to be a simple, classic outfit that you can wear as comfortably and casually as possible! The slip skirt has a beautiful seam detail down the middle that just elevates the skirt over other slip skirts. Pair with sneakers, ballet flats, or flat boots.
Asymmetric Skirt For Work Parties
If you need an outfit for work holiday parties, this is it! It’s festive, work appropriate, and you’ll be comfortable. You should also consider this skirt if you’re looking for options to give your legs length. An asymmetric skirt line is perfect for someone with strong calves because it doesn’t cut straight across your legs.
Sequin Skirt With Oversized Blazer And Black Knee High Boots
This sequin skirt is perfect if you’re looking for something fun for the holidays! I would wear black sheer tights to keep warm since the skirt is a mini skirt.
Black Velvet Skirt With Satin Top And Cashmere Poncho For Winter Events
A black velvet skirt will be a classic piece you can keep in your closet for years. While I styled it here for a dressier occasion you might have, like a holiday party, you can definitely wear this to work or even just to brunch when it’s cold outside. You can complete your look with this cashmere blend poncho to keep warm when you’re going from one place to another. Or, layer this with this exact denim jacket if you want to create a more casual look.
Gray Monochrome Outfit With On-Trend Burgundy Accessories
You can get so much use out of these pieces together and separately! This look definitely works for the office, but you could also wear it casually with sneakers. I love this outfit with boots if you want to dress it up. Midi skirts always look elegant with boots, and these print boots add a fun twist to this monochrome look so it doesn’t feel too flat.
Oversized Sweater with Skirt for the Weekend
Oversized sweaters are a go-to for me when I want to be comfortable! You can wear them with more than just jeans or cozy pants, though. I love the look of an oversized sweater with a slip skirt. I styled this oversized cardigan, which is super soft cashmere, with this black slip skirt to have lunch with friends last year. You can see that outfit on me here – I was a very, very tired new mom! It was spring, so I went for a t-shirt under my cardigan, but I’d wear a long-sleeve top for fall or winter.
Okay, that’s all from me today! Did you find any outfits you love? Let me know what you think!
