Fall & Winter Day-to-Evening Outfits to Make It Easy to Look Good All Day Long

As we start the holiday season, I am sharing over 24 Fall & Winter day-to-evening outfits that I have collected over time. I hope this helps to make it easier for you to go from the extra work to the extra fun that gets added into our schedules at this time of year. But there are dinners and nights out all through the cold Winter, so I hope you make use of this straight through to Spring.

Age doesn’t matter because all you need to do is choose your favorite outfit ideas. Wear what you have and what you love. That way, you’ll feel and look good all day and all season long!

Fall & Winter Day-to-Evening Outfits

These outfit combinations are suggestions meant to inspire you. Make any substitutions that work with your wardrobe and tweak things to your liking. 

I know that many of the photos I found to use as examples mostly feature black outfits. Obviously, that is the easiest color to go seamlessly from day to evening. But jewel tones transform just as well. These are colors inspired by gemstones such as emerald, ruby, sapphire, amethyst and topaz. 

The first section here features outfit combos fit for weekends and lifestyles that don’t require business attire. The second section below focuses on ways to go from your business day to all sorts of evening events.

You might also like to check out my post that has six style tips and 14 ways to dress for day to evening in Winter HERE.

For Weekends & Lifestyles That Don’t Require Business Attire

1. Weekend Casual:  A solid or graphic tee + light blue jeans + a long cardigan. Add flats or sneakers & jewelry of your choice. For Evening:  Change flats to heels & change cardigan to a long blazer.
2. For Day:  Wear a plaid shirt & blue jeans, distressed is okay. Add printed espadrilles if early Fall. Otherwise, choose embellished moccasins or loafers. You might like to add a cashmere hoodie and/or cuff bracelets. For Evening:  Switch to heeled boots and add a statement necklace.
3. For Day:  Layer a black blazer over jeans & a tee, a dress or a pencil skirt & blouse. For Evening:  Add oversized earrings + heels + an evening bag. 
4. Pair a biker jacket with slouchy pants or a floral dress.  
5. Layer a cardigan over a party dress. Then add a skinny belt. 
   

   

6. Dark denim + a dressy top or collared shirt + a cardigan or blazer. Add a trench or woolen coat if cold + heels or fancy flats + a dressy bag.
7. Wear a long-sleeve black sequined blouse with blue jeans & a black or blue velvet blazer.
8. Wear a long black blouse, printed or solid, over sleek bottoms such as leather pants or slim jeans. To dress it up, add a multi-strand gold bead necklace inside the collar + strappy heels + a clutch. 
   

   

9. Top jeans and a tee with a blue blazer & a dressy scarf, shawl or pashmina. Add gold:  statement earrings, bangle & rings.
10. A brown fur-collar cardigan (or add a fur scarf to a cardi) + brown pants + a camisole of your choice. Tie the cardi with brown or bronze satin. Add bronze pumps + dangle earrings. For makeup, use gold eye shadow & contour with brown shadow and then add golden or bronze lipstick. Hair up.  
11. Pair a black or red sweater with black pants. Add a metallic scarf, such as copper or gold.
12. Layer a fine knit over a shimmery top.

From Business to Evening Out

1. For Day:  A tailored suit + a cashmere sweater, a button-front cotton shirt or a chiffon blouse, solid or printed. For Evening: Switch the top for something a bit more seductive (i.e., a lace camisole or chiffon blouse — Or, if your jacket isn’t too revealing when buttoned, nothing at all underneath.) Next, swap your day shoes for something delicate or daring (i.e., peep-toe heels or strappy platform sandals); swap your tote for a clutch & your daytime jewelry for one standout piece.)
2. For Day:  Pair a turtleneck with trousers. For Evening:  Add statement earrings & a chic clutch.
3. For Day:  A dress + cardigan + jacket. For Evening:  Take off the jacket & wear the cardi with the dress for drinks at night.
4. For Day:  A skirt from a black suit + a black sweater set (crewneck tucked in, cardigan as jacket.) Add a narrow brown & black woven leather belt with a gold buckle, gold & carnelian earrings, gold necklaces, pretty brown shoes, brown-toned sheer stockings. For Evening/Instant Dinner:  Switch to a narrow gold belt, gold earrings & bracelets, bare black satin sandals, sheer stockings.
5. Add pearls to a navy velvet dress. Wear skin-toned stockings & pumps.
6. Wear a blazer over a belted dress. Add nice flats. 
   

   

7. Switch from a structured blazer and ballet flats to a cardigan and heels.
8. Combine a black velvet blazer with a purple or jewel-tone camisole or tank & gray pants. For evening, add a statement necklace & ring; you might also like to do smoky eyes & wavy hair.
9. Wear a pale pink shirt as a jacket over a cream blouse & gray pants. Add brown shoes & bag + an ivory knitted scarf + gold jewelry. You might like to add a red tassel to a small brown bag:  buy tassels in drapery stores & attach to zipper pull of bag. 
10. Match a lace top to the color of your tweed trousers. Or, pair a brown lace top with gray flannel pants. Add evening boots & beads.
11. Pair an ivory cashmere sweater with ivory trousers. Add a gold necklace + a chunky gold chain bracelet.
12. Pair a mohair sweater with a black pencil skirt. Add jewelry & heels.

Look & Feel Good While Saving Time

I hope these outfit combinations help you to smoothly sail through your busy days and nights. This should cut the time it takes to decide what to wear so you can just get things done and have fun! With a little creativity, you might just find that you have plenty to wear.

And if you find that there are things you should or want to have, the holidays are a good time to find treasures to gift yourself. After the holidays, Winter can tend to drag on which can also be a good time to comfort yourself with what you want and need. Self care extends to your wardrobe. Looking good makes you feel good.

Wishing you comfort and joy during the holidays and all through the Winter season! 

Let’s Connect!

Did this post inspire you with ways to dress for those days when you go from day to evening events? I’d love to hear from you! Please leave a message in the comments below.

Like this post?  You might also want to read my style tips in “14 Ways to Dress for Day to Evening in Winter” HERE.

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This post is linked up with Fancy Friday at Nancy’s Fashion Style.

Thank you for visiting Your True Self!

Angie

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