100 Fall & Winter Evening Outfits: Ideas to Inspire Your Creativity

This is the last in a series of Fall/Winter Evening Outfits. You can find the rest of the series HERE. Next year I will be updating a number of the posts beginning in October with date night inspiration in honor of Sweetest Day. We are now at the end of winter; spring begins March 19, 2024. Although it’s getting warmer and it seems as if spring will be early for once, we’re still getting chilly spells and even the threat of snow here in Detroit, Michigan. So in the evenings we still need to dress warmly enough. Please enjoy these fall & winter evening outfit ideas. Get ready for some creative inspiration. And I wish you a happy spring season coming soon!

In the outfit ideas below, I have highlighted a basic outfit item in bold type to make it easier for you to scan sections of the list for pieces you might want to use.

For those of you who cannot or do not want to wear heels, I have highlighted the footwear in bold and italics to make it easy to find outfits that work for you. Choose your own footwear in the rest of the outfits that don’t mention any.

These ideas are just that:  ideas to inspire you with new ways to combine what you have. So substitute with what you have, free your true self and make it your own. And remember, age doesn’t matter!

And Now for 100 Fall & Winter Evening Outfits!

All references to leather and fur in this post are meant to be faux in order to be kind to animals.

1. Wear a lace-hem sweater over jeans for a casual evening.
2. Dress up your lace-hem sweater a little more with black pants or skirt & a statement necklace.
3. A lace-hem sweater + a black faux leather skirt.  You might like to add flat black boots to this.

Fall & Winter Evening Outfits With a Denim Jacket

1. Pair a dark color top, such as navy or black, with a black leather skirt. Top with a denim jacket that has lace sleeves, hem or insets. Or simply add a lace scarf or brooches to a dark-wash jean jacket. Finish with black tights & black ankle boots.
2. Put together a chiffon skirt, a top of your choice and a denim jacket that has lace sleeves, hem or insets. Or simply add a lace scarf or brooches to a jean jacket.
3. Pair a denim jacket that has lace sleeves, hem or insets with wide-leg trousers. If you don’t have a jean jacket with lace, add a lace scarf or brooches.
4. A denim jacket + a black lace top tucked into a black lacy maxi skirt. Belt it in gold. Add a multi-strand gold necklace + a gold bracelet or cuff + black ankle boots. If the jean jacket doesn’t have any special touches, add a black lace scarf or some brooches. Turn back the cuffs of the jacket for a modern look.
5. Partially zip a denim jacket over a toned top & animal-print skirt. Add a gold chain belt loosely over the hips. If the jean jacket doesn’t have any special touches, add a lace scarf or brooches.
6. Top a long-sleeve gold sequin top & blue jeans with a jean jacket. Turn back the cuffs to show the gold. Add an ivory or white belt & white or stone color boots.

Fall & Winter Evening Outfits With a Dress

1. A dress + black faux leather pants or snakeskin leggings.
2. Top a velvet dress with an embroidered duster.
3. Or top a velvet dress with a black moto jacket & add black booties.
4. Add a narrow black belt to a navy velvet dress. Add colorful jewelry.
5. Wear a tunic-length velvet shirt open as a jacket over a short black dress.

   

6. Accessorize a maxi dress with a squash blossom necklace & Western boots.
7. Top a black maxi dress with a teal (or color of your choice) velvet kimono. Finish with high-top sneakers.
8. A little black dress + a duster jacket + black booties.
9. Pair a brown wrap dress tall brown heeled boots.
10. A sequined dress + matching leggings + a hoodie toned to the color of the dress and leggings. Add moto boots + a necklace toned to the outfit.
11. Top a sequined dress with a black faux leather jacket. Add gold stud earrings and gold heels/sandals. Put your hair up or style it for evening in your own special way.

Fall & Winter Evening Outfits With a Skirt

1. Pair a sparkly skirt with any top of your choice. Add boots & a scarf and jewelry that goes with the color and/or sparkles in the skirt.
2. A cashmere sweater (black or not) + a sparkly or lacy skirt (long or short.) You might like to add heels + a clutch.
3. Pair a lace top with a faux leather skirt. Add a fringed bag and/or suede boots.
4. Start with a chunky sweater over a long slim skirt. Add long sparkly earrings with your hair up, textured or patterned stockings & metallic ballet flats.
5. Pair a sweater with a long, floor-grazing skirt.

   

6. A black crochet sweater over a dark red camisole or tank + a long black skirt. Add dangle earrings + black boots or shoes.
7. Wear a black leather jacket with an animal-print skirt.
8. Pair a black lacy skirt with a girly top. Add studded boots & some fun jewelry.
9. Wear a denim jacket with lace sleeves, hem or insets over a tulle skirt. If the jean jacket is plain, pin brooches to it.
10. Top a graphic tee & tulle skirt with a leather jacket. Add a cool clutch or fringed black purse & loafer pumps or slip-on flats.

    

11. Pair a lace top with a tulle skirt. Toughen it up with biker boots or combat boots.
12. Tuck a blouse into a floral maxi skirt. Add boots + hoop earrings + a colored bracelet.

Fall & Winter Evening Outfits With a Moto Jacket

1. A long dark floral skirt + a bright-color tank top + a moto jacket.  Add a crystal bracelet.  You may also want to use a beaded clutch.
2. Tuck an animal-print t-shirt into bootcut blue jeans. Top with a moto jacket. Belt it in black. Add gold hoop earrings & animal-print ankle boots.
3. Top a sequin top & distressed jeans with a moto jacket.
4. A lace turtleneck + jeans + a moto jacket. Add big gold hoop earrings.

Fall & Winter Evening Outfits With Lace

1. A lace turtleneck or lace top over blue jeans. Add textured narrow bangles.
2. A black lace top + black jeans + black ankle boot.
3. Wear a lace top & vest in a matching color over the bottoms of your choice. Or combine any lace top and any vest.

Fall & Winter Evening Outfits With a Vest

1. Fasten a biker vest over a long-sleeve top in a dark color & a tulle skirt (i.e., top and skirt in charcoal.) If you need to cinch in the jacket, add a belt such as a chain belt over the vest. Add jewelry of your choice and boots.
2. A brown faux leather vest + a black leather jacket + black trousers.  Add a wide black leather belt, a killer cuff, evening earrings, heels.
3. An embellished vest + a draped top, half-tucked in front + a short skirt.  Add a necklace + bangles + rings + stud earrings + black tights + black booties.

Fall & Winter Evening Outfits With a Cardigan

1. A black boyfriend cardigan + a black sequin or lace tank over blue jeans.  Add wide hoop earrings.
2. A black cardigan + a black skirt or trouser + a white lace camisole. Belt in gold. Add pretty jewels, evening sandals or heels & perfect makeup.
3. Wear a jeweled cardigan over a feminine camisole or tank top & bottoms of your choice.
4. A black sweater + black pants or skirt.  Add a cardigan (red, coral, cobalt, teal, etc.)
5. Wear a gray cardigan over a white lace cami and gray flannel trousers. Add pretty shoes & jewels. Perfect makeup is the finishing touch.

Fall & Winter Evening Outfits With Faux Fur

1. A faux fur-collar cardigan + matching color pants + a camisole.  Add rhinestone jewels or a brooch.
2. A fur scarf + a matching color jersey tunic + some old jeans.  You may want to add heels.
3. Pair a long-sleeve gold sequin top with blue jeans. Belt in gold. Add a furry jacket.

Fall & Winter Evening Outfits With Velvet

I have a whole series on velvet outfits. These are the ones that don’t fit into only one category. I have posts on tops HERE, skirts HERE, pants HERE and kimonos and dusters HERE.

1. Tuck a satin shell top into the pants of a velvet suit. Add gold:  hoop earrings, beads and heels. Push up the jacket sleeves for a modern, laid-back feel.
2. Pair a velvet suit with a silk tank top, such as a bronze silk tank with a navy velvet suit.
3. With a crushed velvet suit, overlap the suit jacket in fron and hold with a big belt.
4. Take a velvet top & velvet skirt in the same color and add a jeweled or satin belt. Add a statement necklace with statement earrings & black heels.
5. Pair a velvet dress/pants/top with some added embellishments, such as silver and crystals.

   

6. Wear a black velvet blazer over a printed or embroidered tunic & velvet or leather leggings.A velvet kimono + a black sequin tank + black leather pants.
7. Tuck a gold sequin top inside velvet pants. Belt in gold.
8. Top a black top & black velvet pants with a velvet kimono/duster. Add black flats.
9. Unbutton a few top & bottom on a tunic-length velvet shirt over velvet leggings. Add gold hoop earrings + a gold chain bracelet + tan mules. 

   

10. Pair a velvet top in a jewel color such as emerald green, cobalt blue or ruby red with velvet animal-print pants. Add black boots & a shawl. You might like to tie a colorful belt around your waist.
11. Top a navy camisole & navy velvet or silk pants with a black crochet sweater. Or choose your own color scheme. Add metallic shoes or boots & bag and crystal dangle earrings.
12. Pair a sheer taupe blouse & loose-fitting navy velvet pants. Slide a navy camisole or tank top under the blouse. Or use the colors you have.
13. Layer a loose short-sleeve velvet top over a long-sleeve black lace top & black skinnies. Add a long pendant.

Fall & Winter Evening Outfits With a Tunic

1. Wear a tunic over leather leggings. Add big gold hoop earrings, a delicate gold chain necklace and a studded cuff.
2. A black tunic + black skinnies + a black duster. Add a long cross necklace with a string of beads + a scarf wrapped around neck + bangles + booties.
3. Pair a black tunic with sequined neckline & skinny black jeans. Add heeled black booties.
4. Pair a black knit tunic with tie-dye or printed skinnies.
5. A lace tunic + velvet leggings in a matching color. Add sparkly bracelets & earrings + flat jeweled sandals or shoes.
6. A beautiful embellished tunic over tie-dye or printed skinnies.

   

7. Wear an animal-print tunic over black snakeskin-embossed leggings. If the top is not opaque, slide a black tee or tank under it. Add a brown & gold shawl. Accessorize with a bronze cuff, ring & earrings. Finish with animal-print booties if you have them.
8. Wear a chiffon tunic over skinnies. Add small gold earrings.
9. A black tunic, such as one with bell sleeves over skinny jeans. Add statement earrings + narrow bangles with a sliver of black.
10. Or take the same black tunic as above and belt it over a maxi skirt or maxi dress. Then you might add a golden or embellished headband.
11. Layer a tunic over a maxi dress. You might then like to add a statement necklace & cuffs.
12. A tunic + jeggings (jean leggings) + a small-heeled in a wintry fabric like suede.

More Ways to Style Fall & Winter Evening Outfits

1. Layer a luxurious silk or rayon top under a velvet jacket or embroidered coat or duster. Or, wear a luxurious velvet tunic under a special bomber jacket.
2. Wear a black cape over a long-sleeve top and skinny jeans or jeggings. Add biker boots.
3. Add a jeweled belt to a black sweater & pants.
4. Dark bootcut jeans with a blouse and a blazer.
5. Wear a tan leather jacket over a tan t-shirt & blue jeans.

   

6. Layer a white v-neck sweater over a long-sleeve gold sequin top with trousers. Shoot the cuffs of gold.
7. A cream shirt under a red sweater + black trousers or brown tweed pants.  Add brown high-heeled sandals, red toenail polish, a small brown leather bag with a red tassel (buy in drapery store and attach to zipper pull).  Add gold jewelry.
8. Top a white tee and jeans with a tuxedo jacket.
9. A tuxedo jacket + a lace or crochet top + any bottoms. Add a gold bar necklace.
10. Layer a long-sleeve top under a caftan that has animal print on it. Add an animal-print scarf & heeled boots.
11. Add animal-print boots to a caftan that has animal print on it. Add multiple long gold chain necklaces.
12. Tuck a white ruffled shirt into blue jeans. Belt in a light color. Add a gold pendant + a narrow gold bangle + some earrings + tan footwear.

    

13. For a museum opening, dinner party, cocktails, etc.:  With a black cami & black velvet or velour pants, wear a gold or other pretty blouse open as a jacket or a 54″ square of silk. Add a black & gold belt and black satin shoes.
14. Afternoon with a friend, or dancing at a club: A short-sleeve gray t-shirt + a short, black leather skirt + sneakers.  Add a cool necklace.
15. Parties:  A silver drape-neck top + a skirt + heels. Add some sparkles & a shimmery wrap.
16. Party dresses:  Belt an embellished cardigan over a party dress. The belt can even be a casual one, such as tan.

Let’s Connect!

I hope this was helpful to you and that you get use out of this outfit inspiration. Please let me know what you think. Leave a reply in the comments below!

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Cardigan, Dresses, Fall & Winter Evening Series, Faux Fur, Lace, Skirts, Tunics, Velvet, Vests