In the continued attempt to not constrict my crotch/stomach with uncomfortable clothes and yet still feel/look put together when I leave the house, I’ve had to make a pretty big winter life pivot. I’ve worked from home for the last ALMOST FIVE years so my tolerance for being uncomfortable when I do leave the house (rare) is very, very low. Of course, I’ve adopted the drop crotch pants but as you can imagine not everyone (ahem, Brian) is a massive fan of the cool “saggy bottom” look, and yet the super baggy jean trend doesn’t look good on all of us. As you have probably surmised from years of seeing me wear teeny tiny shorts I’m more apple-shaped (I carry more weight on my top than bottom) so I like a blousier top and skinny jeans. But skinny jeans aren’t that comfortable (some are) and apparently they are not having a moment right now (but rumor is coming back soon???). Also, I feel so frumpy in the “blouse on top and baggy on bottom”. So this winter for going out I’m leaning into the structured mini skirt – with tights, socks, and boots. Here are a few that I’m loving (and more affordable options at the end).
A Patterned (And Quilted) Number
Jacket | Shirt (similar) | Skirt | Socks (similar) | Shoes
Here we have a quilted plaid skirt that I just bought. I paired it with a fancy sock because that’s a thing apparently and I think I like it (especially with those pumps that I got years ago and rarely wear). The denim blazer is the one from Madewell that I love (roomy but still flattering). I bought both a size 4 and 6 in the skirt and much prefer the 6.
A Large Floral In A Tiny Skirt
Jacket | Blouse (similar) | Skirt | Boots
While Brian remarked how this looked very sofa fabric-esque (not wrong) I LOVE this “suit”. I bought it for an event then realized that in Portland I might have stood out more than I wanted to while I was there (I was right). This is thick brocade-like fabric and really busy (and thus forgiving). Of course, these boots are the star of the show (and come in blue suede, too which I wish I had bought but I love these).
This matching jacket look might not be for everyone (or every occasion) so I also tried it with an oversized sweater which is probably what I’d wear more often.
The sweater is old from Alex Mill and has a cute boxy cut with dropped shoulders. It takes what could feel more statement-y and calms it down a lot. The skirt is short but pairing it with suede over-the-knee boots (are we still saying thigh-highs?) covers up most skin and would look cute with brown tights, too. I also like the boots being suede instead of leather as it also tones it down a bit.
A Little Denim Number
Sweatshirt (similar) | Bandana (similar) | Skirt (similar) | Belt (similar) | Boots (similar) | Bag (similar)
I’ve had this skirt for a long time and just unearthed it (same with the boots!). I threw on a vintage sweatshirt, bandana, and belt (although I think I’d skip the belt next time).
This feels far more fall than winter, but tis the season 🙂
A Black Leather Mini – But Make It Serious 🙂
Blouse | Skirt (similar) | Tights (similar) | Boots (similar and only $25!)
Another skirt I’ve had forever that I’m so glad I kept (same with the shoes, but these are so close). I wanted to calm down the vibe of the black leather with tights, wooden-heeled shoes, and again, a blousy top (I just bought this for a huge shoot I had a few weeks ago).
I really look like I love drinking coffee in my mini skirt ha. But honestly, I do really love this look and feel good in it. So if you are interested we pulled together a handful of affordable options with some great size-inclusive picks too!
- Denim Micro Mini Skirt | 2. High-Waisted Mini Skirt | 3. The Colette Faux Leather Mini Skirt | 4. Jacquard Mini Skirt | 5. Denim Mini Skirt | 6. Houndstooth Mini Skirt | 7. Saddle Wrap Mini Skirt | 8. Faux Leather Mini Skirt | 9. Corduroy Miniskirt
Happy Saturday and happy mini skirting. xx
*Photos by Kaitlin Green
I was not a fan of the quilted and got really worried when I saw the sofa/tapestry suit, but yay for continuing to scroll because I LOVE the tapestry skirt with the blue sweater! I think I’d like it even more with a grey-sage sweater. The denim look is fab (IMO), as is the black. Very psyched about the “shop your closet” approach to some of these looks – a good reminder that, with a dash of EHD inspo, we often already have what we need!
Nooo I love the tapestry suit with the boots! It’s so artsy! Why NOT stand out from the crowd?
Same! Although I understand that the audience is key here and some locales/industries just don’t communicate the same way. The floral set feels very Ulla Johnson, which my sister wears all the time in her Chicago scene. In my Minneapolis world however it can read as try hard. So at the end of the day wear what makes you happy. But deciding how and what you are communicating to others is certainly part of that, imho. And women, can we agree to support each other and not call out choices others would make that we oulent but celebrate them instead? We will all be happier if we can do that.
I completely agree here Michelle. Depending on where I am in the world (literally) and which event or occasion I am attending, what I wear either works or is completely inappropriate. Case-in-point, I spend a lot of time in Maine (my home state) where practicality and classic-simple styles rule. It takes nearly nothing to look like I am trying too hard (too fussy!). Here in Maine Blundstones and Dansko are considered fashionable. However, when I am working in Virginia, people look at me (wearing those shoes) like I have 2-heads (of course I wear them anyway!). At 53 I could care less what people think of my fashion choices, but I definitely do not try to stand out in certain situations. While I personally prefer a more down-to-earth style vibe (like an Alex Mill look), I always love seeing people dressed in their unique style (like the floral “suit” here!).
I actually love all the skirts (although I no longer have a body suited to them).
Does anyone have recommendations for comfy (not constricting in the waist) tights? This is often my biggest hang up with wearing skirts/dresses in cold weather.
JJill actually makes great tights that with some care last years.
https://www.gudrunsjoden.com/en-us/clothes/accessories/product-126828-black-s-m
Snag tights are very comfortable at the waist but don’t fall down, highly recommend!
Cute! Can you do more posts about dressing up for Portland? Because this particular intersection of occasion/location has me totally stumped. You want to look cool and elevated but NOT fancy or glam; not even a little bit. Help?!
Yes! I mean, I live in rural Nova Scotia, but I think there might be some overlap. I own very few clothes (after my last donation run, less than 20 items total). I decided to keep only what I actually wear…but do wish I looked slightly less grungy while still prioritizing comfort and function. And I pretty much only buy things I think I’ll wear on repeat for years. Craving flannel lately…
Dana, I am “next door” in Maine and always crave my flannels this time of year. I have been trying new layering ideas this Fall with them and am finding that if I throw on an Alex Mill jacket (I LOVE my cobalt Britt one!) I instantly look more out together but still have the comfy flannel look that I love. If I really want to elevate the look, I throw on a scarf with it all. With the right boots, it’s comfy, practical (for our weather), and classic. It’s really become my uniform for the past 3-4 years here. I just rotate different colored flannels and scarves and it’s still a fun wardrobe!
Oh, that sounds perfect, Stacia! Thank you for the inspiration!
Since we are talking about mini skirts, I just ordered this one from Loft: https://www.loft.com/petites/petite-skirts/catl000039/750271.html?dwvar_750271_color=503438&dwvar_750271_size=049¤cy=USD&country=US
And it’s on sale now!
Since these adorable outfits of mini skirts and high heeled boots are presented in the name of comfort, I’m sort of curious – is it really comfortable to sit in various heights of chairs, bend down to pick things up or plug in a charger, climb stairs (especially with people behind you) in these outfits?
Don’t get me wrong, Emily looks cute as a button here, I’m just thinking of my real life, where I drop things on the regular 🙃
Wearing leggings with them makes them comfortable because you don’t have to worry about modesty. They become an accessory. Not the same affect with tights. Having to keep them arranged for modesty can be tricky.
I’m not Emily, but I am clumsy, so I feel somewhat qualified to respond. I find that a properly-fitted skirt that nips in ever so slightly at the bottom hem paired with a pair of opaque black slip shorts keeps me feeling covered and comfortable all day long.
I have 3 kids under 8 and my favorite outfit in fall/winter is a black t shirt dress with a long cardigan or a long sleeve t with a structured above-knee skirt and opaque black tights. I find it very comfortable and makes me feel cute too! I buy opaque tights from h&m which are great quality and inexpensive in case kids’ Velcro shoes ruin them.
You look fantastic in these outfits! Rock it, girl. I am not and have never been a skirt person… dresses, yes on summer days when I am feeling the dress vibe. Is it just me or don’t you all find that skirts (especially structured ones!) lift up when you sit down so that the waist is at your ribcage and suddenly the hem is inches shorter than you planned?? I’m hourglass shaped and can only imagine it’s worse for people with straighter waists. Anyway. I can appreciate this shoot a lot and also not feel the least need to try it myself.
Em the skirts are super cute. I wear short skirts and dresses every day of the week and never wear pants to work. I find the perfect length for me is about 17 inches for a skirt and 37 or more for a dress (I am 5’6″). I look at the clothing descriptions to eliminate some cute but too short for me purchases. All winter I wear black tights and a block heel pump or boot (stability!) with the dresses or skirts.
Watch out for sitting in a skirt shorter than 17 inches, that baby will ride up and you will risk flashing the “cash and prizes”. So much easier with tights.
My favorite black tights are at Target. A New Day High Waist Control Top Opaque tights. They go in the washer and dryer. Only $9 a pair. The waist band will either be at your waist or above so you will not have to worry about pulling on them to get them above the waist band of your skirt–a nice slim line.
now do a fit and flare round up? Love that silhouette.
Ohmygoodness, yes to the structured skirt and tights combo for those of us with the same fit/comfort issues! (Why are pants always too short in the rise??) It’s always been one of my favorite outfit options and I still have some old favs in the rotation. May have to welcome a couple of new kids to the closet!
I really love this post – super fun and made me want to try something new. Thanks!