You look beautiful in your outfits, really wonderful. I do like Rachy's advice of something that feels like you, but just a bit fancier. I can see that with my dresses, they all have a similar structure and fit. No plunging necklines, fussy detail or potential wardrobe malfunctions and I can wear normal underwear, a strapless bra is as exotic as I go!

I think Rachy hit on the issue: in the 2 photos I look like 2 completely different women. Neither would I say looks like my version of “me.”

I remember thinking at the wedding in picture 1, “this is not about me, this is about 2 fantastic young people, my family, who are super cool and I am so proud of them. I’m going to have a heck of a good time celebrating them.” Then I did.

Just want to forgo the angst I put myself through for the next fancy event I want to attend. You all have been lovely to offer all the wisdom and kind words.

I do have a formal capsule, as hubby and I have lots of formal occasions throughout the year, which range in their level of dress code. Hubby also has a formal capsule, which includes a couple of kilts and tuxedos.

Attached is just the current dress portion of the capsule. You'll see I pretty much stick to a basic silouhette that I find particularly flattering for my figure: cowl neckline, ruching at the waist, stretchy material. In fact I have a few "go-to" petite brands (Ralph Lauren, Calvin Klein, Connected) that come out with this basic dress year after year with various "glitz" factor added like sequins / metallic fabric / etc. And when on sale -- they aren't outrageously expensive -- so I snap them up!

Recent adds include the metallic silver dress, as I had a silver anniversary to go to. This dress is tons of fun and can be dressed down with a jean jacket. The velvet bell sleeve dress got snapped up early on in the Fall because I'm always looking for something to wear to our February formal event, when it's cold (rare to find such good arm coverage AND thick fabric in a formal dress). And I *finally* found a full length gown that needs no hemming and doesn't overwhelm my frame!! Snapped this one up on sale and have yet to wear it - will wear it next year for sure.

Not included are two sheath dresses (black and navy) which I wear for work but which can be easily dressed up for work-related dressy events (just add fancy jewelry, clutch, high heels and bright lipstick). I have an annual work cocktail attire event in which I've basically been alternating this dress each year, changing up the jewelry and clutch, and nobody's been the wiser. If I was invited to a wedding and wasn't sure about the dress code the navy sheath would be my "go-to."

I also have a capsule with mix-and-match separates including metallic blouses, velvet top, velvet pants, tuxedo blazer. This gets a lot of use during the holiday party rounds. Can easily wear the tops/toppers with dark wash jeans if the party is going to be more "smart casual" than formal.

Shoes: are a challenge. I am down to one pair of pumps that I can wear for more than an hour -- the nude pumps shown. Luckily they are neutral enough to go with a lot of dresses.

I also have a pair of (inexpensive) gold sparkly flats for when I want to swap out the heels to walk to and from an event.

I have a small capsule of dressy shoes, bags and jewelry but only a few clothing items. While I like to wear dresses for casual and work wear, cocktail dresses aren't really my thing. So many of them are too short or too body con or too bare, or they look matronly. A few years ago we attended a gala and I found a jumpsuit that on its own wasn't really dressy but I added a blingy belt and with dressy shoes, bag and jewelry it was perfectly appropriate and best of all it felt like ME. Which might be while I had a great time that night!

Chris you look fab in your outfits.

I like the advice given here - by several including Tulle. Find an elevated version of your best outfit. Fit can be an issue and the pressure of how you think others want you to look.

I adore occasion dressing - but I think I have a love of cocktail dresses and heels and stoles... I find it easier than casual dressing or work dressing which I think is odd.

There are times that we may not have the perfect outfit - time constraints, budget, fit issues - in that case I think wearing a very simple blending type dress or pant suit with your best hair shoes and make up. I think it is worth having a dress or outfit like this in the closet available. It might be a LBD or Le Smoking or a silk shirt and ankle pants. I hope my new black lace dress will be my go to for these occasions. I will wear a slip and heels tho!!