Dresses Review
In case you missed my last post, this is part of a new series where I’m going through each category of my closet and talking about how I break it down by subcategory to analyze my current style preferences and understand my future needs. I own a total of 34 dresses which honestly to me, isn’t that many probably compared to others who live in warmer clients. The thing about San Francisco is that give or take 20 degrees, it’s pretty much the same year round. Doing this exercise did help me identify some blaring holes though.
Dresses is such a fun category because they really can say a lot about your personality. Most of the one’s I own really fill the charming bucket of my personal style filters with feminine details like scallops, puff sleeves, lace, ties, rouching, ruffles and floral prints. Overall, when I look at my dress collection, I see my preference for maxi styles and silhouettes that can be layered with a sweater or jacket with ease, which I suppose hits the comfortable bucket of my personal style filters. The one style filter that doesn’t seem to have a big presence here is classic.
I love wearing pretty, yet still casual, day dresses out for weekend events like lunch or a trip to wine country. I also love to pull a special printed one out of my closet for events, whether that be a conference, workshop I’m hosting or a networking party. I could use a few more easy year round options, as well as casual options for both summer visits on the east coast and those occasional super hot SF days. I think it could also be beneficial to experiment with some more classic styles and colors. For as much as I love black, I feel like I could use more dress options that are both dressy and casual. Although keeping in mind that while I do love the idea of more tailored styles, they aren’t always the most practical. So there’s a fine line to the definition of classic for me and I need to experiment with it! I did notice from the photos I curated below that some of the classic hits come through in footwear and bag styles.
Okay, let’s talk about how I define and analyze each sub category!
1. Casual
In the casual category, I own a whopping total of 4 dresses! I define this category by fabric and silhouette, those that are lightweight and easy to throw on over a bathing suit or with sneakers. Gauzy cotton, linen and lots of solid colors. Flowy and not too fitted. I really could use some more options for summer travels back to the east coast as well as to throw on to hang at the park on a super warm day. Also because I don’t find myself in a bathing suit often, I realize that when I do my coverup options are always a challenge.
To be honest, even though these tend to be inexpensive, this just isn’t my favorite category to shop for because they aren’t as emotional and exciting but I do see how that thought makes me avoid and neglect my practical needs. So adding a few to my shopping list now!
2. Season-less
I only own 4 options in this category. I hesitated to even include this as a category but I realized there’s this handful of dresses that I rely on anytime of the year because they are easy to layer for San Francisco and the prints and color direction lean more neutral and season-less. My most worn dress in this category is the Jenni Kayne Rio Slip dress in Moss because it is both perfect on it’s own in the hottest months as well as layered up with a chunky cardigan for the cooler months, talk about versatility!
3. Fashion Spr/Sum
I own the most dresses in this sub-category, 11 to be exact, probably because they are so emotional! I’m a sucker for special details, novelty fabrics and unique prints. This category also leans really pastel and floral due to the nature of the season. Lots of poplin and textured fabrics that lend themselves specifically to these months of the year.
However, I’ve also realized that any dress that feels too girly and can’t be easily styled with sneakers or something more practical to ground it, rarely gets worn. I need to keep this in mind before pulling the trigger in the future!
4. Fashion Fall/Winter
While I only own 5 dresses in this subcategory, all of them serve a purpose. I have a red sweater dress, perfect for the holidays. Two fall floral mini dresses cute that look cute with boots. An earthy toned maxi, perfect to dress up or down. And an easy floral printed maxi perfect for sneakers and more casual wear.
All styles in this category are darker in color and typically heavier weight fabrics. I would love a few long sleeve sweater dress options as I do think this is a type of dress I would get a lot of wear out of in San Francisco. I’ve been ignoring it because it’s not as exciting to shop for but I am taking notes on that as a theme that keeps popping up!
5. Overalls & Jumpsuits
I have a few special finds in this subcategory, 4 to be exact that I love and wear occasionally. I don’t have any big reflections for this category as they’re not really a need and more of a find if something catches my eye! Who doesn’t love a one and done outfit here and there? I do, especially when they can be styled with different accessories. Honestly, I’ve found the Levi’s jumpsuit below to be a little limiting in that respect and when something feels too mundane I pass over it.
6. Special Occasion
Dresses in this subcategory include those perfect for weddings and celebratory events, like New Year’s Eve or a big birthday milestone. Like the Cara Cara one below I found on The Real Real earlier this year and plan to wear for my 40th birthday next year!
I own a total of 5 in this sub-category and tend to invest in nicer brands, quality and more classic fits that will stand the test of time since I hate buying things I’ll only likely wear once. I could probably use another versatile little black dress option at some point as the Diane Von Furstenberg one I have and love is probably a decade old already. Wow I can’t believe I’m saying that! And also how cool when you can.
Things I want to try or have...

I think I’d like to eventually double the amount of options I own in this category. Since dresses tend to be so special, I’d like to have more options and wear the ones I love even more sparingly so that when I do, they feel even more joyful!


