I have problems with this too. I'm going to flag this post for future reference. I like to wear heels since I don't wear them normally and I enjoy heels. But they don't always work for the occasion (nothing that requires a lot of walking). I don't have any tops that are that magic level of dressiness and sexiness. I think this is an area I could work on as well.

Yes, lots of great ideas and finds, photos here. Very inspiring. I hope your search and wardrobe development are successful.

I wore #2. The top is a heavy satin material. And yes, I’ll wear #3 and the other two within the next couple of weeks, while it’s still warm, as all of a sudden we have a busy social calendar!

Wonderful, cjh!

Little black or almost-black dresses tend to be my FFBO in this type of situation. I like doing dresses for dress-up because it gives me a chance to wear statement tights: I have a good variety of textured, colourful, and sparkly tights, and if I don't wear them for night-out type events they just don't get worn at all, because when I wear my dresses during the day I almost always choose leggings for durability and warmth.

The jeans-and-blouse combo often comes off a little too "everyday" or office-y on me because I don't do heels. With a dress I can get away with oxfords or booties and still look like it's a special occasion. If I ever find the perfect pair of edgy-looking flats or low heels, or else a pair of slightly daintier boots than the ones I have (part of my issue is that I like to have some element of juxtaposition), I could probably pull together some better "festive jeans" outfits. If I could wear pointy-toe heels like the ones you show I would definitely feel sufficiently dressed up in jeans and a silk top, but my feet would be miserable.

I generally go out 3-4 nights a week, either to sing jazz at open mic sessions, or dinner + drinks with friends.

I don't have quite enough time to hunt down examples to add to finds right now, I'll try to do it later. I have three FFBO, in order of more dressy to less dressy:

1) Pencil or tube skirt that hits at the knee + ocean-colored top and/or a topper (I have a white J Brand denim jacket that's gone everywhere with me this summer, or my trusty black zip-front cardigan) + high heel pumps or dressy sandals + delicate stud earrings and a statement ring + crossbody bag.

For cooler weather, I wear heeled boots, and a leather jacket.

2) Same outfit, but swap the top for a plain or graphic tee. Everything else is the same, except I might wear more casual wedge sandals.

3) Skinny jeans + plain fitted tee or bodysuit + optional topper + high heels. Same jewelry + bag. I'm pretty easy that way.

I think what makes me feel special, is that I try to dress in my favorite mermaid colors, and I take special care with hair, makeup, perfume, and nails.

It depends on the occassion. Drinks or dinner with friends is different than classical concerts.
I have a few bottoms I use with different tops.
Drinks etc: jeans in all colors with a dressy silk blouse, or t-shirt with jacket.
Shoes/boots with a little heel, but that I can walk in from my free parking spot.

Concerts /theater: like la BD I use "little black skirts". Kneelenght with a dressy blouse or sweater, lace, everything goes. Easy and with dark hair I can use black stockings and shoes. The skirts are a bit fitted and the tops a bit looser.

1. Jumpsuit with wide legs, high heels, red lipstick, clutch.

2. Dark wash jeans, heels or pointy toed flats, with flowy blouse that has interesting details like fluted sleeves or is off the shoulder (but I don't do off the shoulder -- like it on others!)

3. Leather jacket with dark wash jeans or black 5 pocket ponte knit pants

4. Otherwise minimal outfit with a clutch in a pop of color or interesting texture like animal print or metallic

5. Tweed fringey jacket or black wool blazer with sleeves scrunched to the elbow over dark wash jeans over a shell top or graphic tee with jeans (dark wash or distressed).

6. Column of black with a white denim jacket accessorized with a pop of color or animal print somewhere (clutch, shoes)

7. A dress (could have color) with a denim jacket or leather jacket.

8. Fabulous shoes (like my new brocade slides from Jcrew) and the rest of the outfit minimal.

9. White jeans with a black or navy sleeveless top and a statement necklace.

10. Skirt (though I'm off skirts right now) with hemline shorter than I'd normally wear with opaque tights, tall boots, and a sweater tunic.

Plain black sleeveless shell with one of my dressier jackets (black shrunken blazer, black cropped jacket, red linen/lace moto, and others I can’t recall right now. Pairs wonderfully with black work trousers, nice jeans, black tube skirt, printed skirts, basically any of the bottoms in my closet. Shoes are usually either patent oxfords or pointy booties.
In the summer I’m more likely to just throw on a dress and flat sandals, but otherwise this formula works with pretty much everything and for both work and evening.

Faux leather leggings, drapey top, a cool jacket. And interesting shoes

I love going out to dinner. We often go with our best friends, so 4 of us. Sometimes just DH and I go if we haven't got out much and have been working too hard. We went tonight but this was very casual with no booking so I wore a long flowy boho top with cardigan over, jeans and sneakers. But I often try to dress up a bit more with either top and pants with higher heels than usual provided not much walking, or sometimes a dress or skirt with boots ( winter) or heeled sandals ( summer). Sparkle somewhere often in earrings, tops, or shoes. More makeup than my usual which is only lippie and blusher.
Here are some old dinner pics. Lots of variety.