Thoughts on Dress-a-Day

Chalkboard Coffee Cup

Welcome to Day 6 of the challenge! I love that unlike my Project 365, I don’t to think very hard about the day I’m on because it’s the same as the date!

As we’re nearing the end of the first week of dress-a-day I thought I’d post a few wonderings I’ve come across through the challenge so far:

Casual vs. Formal

-Dresses have the tendency to make me look more formal than my normal attire. I think maybe because most of my dresses were bought with the intentions of wearing them to nicer events like weddings and graduations. I have very few (exactly 3) casual t-shirt style dresses for everyday wear.

-Accessories can tone down the formality. I really need to get some cute jean and khaki jackets to help dial down the “niceness” of my dresses. They can be everyday if I don’t style them with pearls and heels!

-I think the reason I fell out of wearing dresses with any regularity was due to the formalness of my current selections. I’m hoping to open up the possibilities for casualizing my dresses over the coming weeks because they deserved to be worn more!


-I’m weird about shoes with dresses. As I mentioned in the previous section, I almost always wear heels with dresses and I stress out if I can’t find a pair of shoes that look good with a dress. Is there a way to define shoes that look good with dresses? It seems to be something I can’t describe, but I know what it looks like (and what it doesn’t look like).  I want to branch out on this point and really did yesterday when I wore the chunkier black flats with knee socks and my navy dress.

-I do of course wear sandals and ballet flats from time to time, but I desperately need new ones. I figure if I have a reliable pair black, brown and silver sandals for the spring/summer and some black ballet flats (which I need to get, my last pair died after three beautiful years) I should be good. I’m by no means a shoe-a-holic, but it amazes me that with the number of shoes I have I never seem to be able to find the perfect shoes for an outfit.

-Maybe I should by shoes for specific outfits. I often buy shoes I like or the aforementioned staples without too much regard to what I’ll wear them with. Though my sister scoffs, comfort is huge when I pick out shoes. I’m not into beauty as pain for 8 hours or more in shoes.

Hose/Knee Highs/Tights and the like

-Do people still wear pantyhose? I don’t see it very often anymore and I’m not sure if it’s a faux pas or old fashioned thing now, but I think hose can be tasteful considering the occasion. What do you think?

-Knee highs. Do they make you look like a school girl? Are they back in fashion as a trend? I’m still tiptoeing into this area. I think knee highs and over knee socks have great potential for spring and fall dress and skirt wear. For spring you want to go for the lighter, brighter colors than with the dark blacks, navys and grays of fall/winter. I’d like to get some more to play around with in the future. (I believe Forever 21 has a large selection)

-Tights. They are definitely the go to accessory for winter and cool day wear of dresses and skirts. I love the different colors and patterns for tights that have come recently. I bought a bunch in the fall. However, I have yet to try to footless tights. I was about to take the plunge this past fall, but my sister talked me out of it. Are they a passing trend or a here to stay staple? I see a lot of you wear them.

These are just some things I’ve been pondering on. I’d love some feedback from the group on how they view these “issues.” Is it just me who stares into my closet and deals with these warring wonderings on fashion, comfort and acceptability?

What do you wonder about?


2 thoughts on “Thoughts on Dress-a-Day

  1. Personally, I see pantyhose as quite old-fashioned, but really it all depends on the styling. I think that people can pull off black or a fun color/pattern if you pair it with a trendy dress and accessories. But if you are just slipping nude pantyhose underneath your “work clothes” just to cover your legs, it seems very out-of-date and “old lady.” Even my mom doesn’t wear pantyhose anymore!

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