Slimcat- I’m glad I’m not the only one!

Angie, point taken, I likely emerged from the womb in a frilly skirt and teeny kitten heels!

I can't even absorb all the good advice on this thread this early in the morning, but thank you for starting it Lynette!

You have my sympathy. I am hard to fit too, so when I find something I like, I get it and worry about building an outfit around it later.

When I buy something new, I do an outfit try-on session at home. If I can't find anything that works with the item, I try to figure out why. Is it the color? The fabric? The length? The neckline? Or maybe I need certain styling hacks to wear the piece well (tucking, cuffing, etc.). Then I can start to form a shopping list of pieces that will help me wear the orphans.

Sometimes I also look online for outfits that incorporate a similar item to the orphan so that I can get ideas of how to complete the outfit. For instance, if I have an asymmetric midi skirt that I'm having a hard time with, I might search for "how to wear asymmetric midi skirt."

I have found that the orphan situation improved for me over time as I added items to my wardrobe that were in a variety of cuts and silhouettes. This means I have a pretty good chance of having something on hand that can complete an outfit. I now have only a handful of orphans. I do have a fair amount of pieces that aren't mix-and-match, however, and have to be worn with a particular top or bottom to look good. I don't mind because I like repeating outfits.

ETA: I have tried the solution of not buying a particular item unless I can also buy completer pieces at the same time, and that's simply impossible for me. Since my size is not very plentiful at retail, I have to buy the item in isolation and worry about completing the outfit later. I usually shop online for the completer pieces. If I don't have much luck, I may decide to return the item unless I'm in absolute love with it.

Gigi- we sound very similar, except that you have solved the problem better than I have! I find it nearly impossible to buy a completer piece at the same time as well. Coming up with one item is hard enough! But that is why I end up with orphans. Your suggestion to look online for how to style the item is excellent. I will try that!

I have no hesitation whatsoever about returning items that don't work with the rest of my wardrobe. Nearly all my purchases are online and were even before the pandemic. In stores, I wouldn't necessarily be completely accurate about whether an item would *go* with the things I had in mind -- so why not order online so I could try on stuff at my leisure? I order 90% of my clothing from Nordstrom and return to the store. They have an exceptional return policy, do alterations, and have repaired items that have fallen apart. What's not to love?

I've learned over the years that I buying in person (and on impulse) from discount stores, outlets, and thrift shops has left me with orphans so those things are not bargains. Instead, I put stuff in my online Nordstrom Wish List and wait for them to be marked down -- which happens more than one would think. It also gives me time to cool down and think about whether I want the item.

I am 5' 1" so a Petite with extra short arms and legs, but I can sometimes wear regularly sized dresses and skirts when they are cut (IMHO) indecently short. When I order anything, it's always a risk. I do not have the guts or optimism to hold onto anything that needs additional items to make it work; there's just not enough out there.

With all that being said, it's a lot easier to have very few orphans when one has a large wardrobe like I seem to have accumulated in the last few years. More choices! But my color palette is extremely narrow. I've also figured out that (to my eye) drapey for the most part doesn't go with strict crisp tailoring, but a very few things can work with both.

Good luck!