Going on a very long overdue date with hubby tonight. Super excited as it's a jazz club downtown I've wanted to visit for a long time. I'm way out of practice in dressing for going out at night so I could use some ideas.

I was going to use the occasion as an excuse to dress up (in a dress and heels) but when I mentioned to hubs my plan, he said I didn't need to dress up that much. Bubble bursted.

In all honesty he is correct. I confirmed we will be taking public transport (bus and subway) and it gets chilly at night. Enough for a jacket or lightweight coat. We like to get off the subway early and walk a bit so walkable shoes must be on the docket.

I know you guys don't know the exact pieces in my closet but could you give me ideas or formulas to use? I'm sure jeans will be fine and I have black dress pants as well.

Some of my ideas to date are:
outfit 1:

Black pants
Silk sleeveless top
Black leather moto - would prob keep on inside unless really hot (questionable bc it is a small venue, I'd prefer to leave on and am afraid to get caught needing to take it off but not wanting to)
Black booties

outfit 2:

Dark denim jeans
White button up shirt
Black moto or black trench

scarf or too fussy?

Black booties

outfit 3:

Jeans of some sort
Top of some sort
Gray knit blazer - can prob get away without a coat this way

outfit 4:

Not a dress, haha, but the VC black tube skirt with some top and maybe some booties I have? Taupe or cranberry suede booties are options.

I dress to make myself happy but I also want to consider hubs' preferences. I want to feel feminine and pretty but still be able to walk on cobblestone and to/from public transport.

Ideas are greatly appreciated!!

sorry for spacing errors, started thread on ipad and ended on PC