As a proud “apple-shaped person” (bigger on top, smaller on bottom) I love the look of the smaller top with the big flow skirt but it’s not a combination that I feel my best in (as you know I like my tiny shorts/skirts or tight jeans and blousy tops) so I just kinda never thought to really try a maxi skirt. But recently I tried one on with a vintage sweatshirt and I was like “Hey, look at that! I can do this too”. It’s so comfortable, easy to wear, and perfect for transitional seasons (aka spring or maybe when our legs are tanned enough LOLOLOL – my legs are always orange, don’t worry!!)
The Great (one of my favorite brands, albeit highly splurgy) and Claire V (same) always nail this look – the casual on top and more feminine on bottom, and one of my best friends works for The Great and styles things to be just so effortlessly cool (shout out to Suzanne). Here’s what she does, which I have copied.
Jean Jacket (similar) | T-Shirt | Skirt | Boots
- The top of choice leans more “masculine,” maybe a crew neck sweatshirt, a vintage band T-shirt, etc, but can’t be too bulky (because the bottom is so voluminous). This could be an old t-shirt, or a ripped sweater. You can certainly wear a ruffly top with this skirt but it looks more formal and less everyday (IMHO).
- Tuck in the front of that top. You want to see the waistline so it’s a tad bit more defined.
- Wear with the “wrong shoe” i.e. sneakers, combat boots, Birkenstocks. While the inclination might be to wear a “girly” and flowy skirt with heels or cute flats (and obviously do WHATEVER YOU WANT) if you are trying to dress this down and look more “everyday effortless” then copy what all these ladies do. And listen (without laughing, but I find fashion hilarious so go ahead and LOL) looking “comfortable” is IN these days (to some of us, thank god) so now is your chance to not have to wear heels (still hard for me quarantine).
I hadn’t really planned on “modeling” this outfit (Kaitlin literally just caught me in what she thought looked cute and snapped a few photos) so I might have styled it even better TBH or added some layered chains/taken off the jacket, but you get it. It’s best to keep the top a bit messy/masculine (a simple muscle or tank will work) and the bottom a little more breezy/full. Add a baseball hat for the full “I’m a celebrity that is trying to not get noticed in Erewhon” effect. Lol.
Here’s the cool and stylish Suzanne, who styled us both for a fashion photoshoot a few years back. What a cute and easy outfit! Casual Top + Fun Skirt + “Wrong Shoe” = A cool and comfortable look.
Sweatshirt (similar) | Skirt | Sandals
The outfit I referred to in my intro was this one and it was very comfortable.
Sweatshirt | Midi Slip Skirt | Heels
I also wanted to throw this look in because while it’s not a super flowy shirt and is more of a midi, the rules still apply! This would look great with Converse or boots.
My team curated skirts for those who are into this transitional style (hopefully, you already have some in your closet). If you like to have a little extra lift in your shoes, then I suggest you try the New Balances that come with a small platform. Or a Teva slide or platform shoe (like this).
It’s not super flowing, but the skirt is definitely wavy. The details are really cool, and it looks pretty comfortable. Plus, it’s from Farm Rio which we can attest for their awesome quality.
Would you guess this was from Abercrombie & Fitch? The pattern is perfect to really play with the masc/fem mix of pieces and it’s great that while the pattern is busy the color is quiet so it’s not too loud if that’s what you prefer. Also available in other colors and patterns!
What a great, bold but casual stripe! The linen fabric has so many uses.
Another neutral, but boldly patterned skirt. This extra-long necktie is also cool. Imagine how great it would look with a vintage band shirts and leather jacket!?
A whimsical spring skirt? This skirt has not only an eyelet hem, but a lace trim as well. It’s easy to wear with a crewneck sweatshirt.
The print on this shirt is fun and stylish! Think about it, you can wear a loose tee with comfortable shoes during the day, and then dress it up at night with a fitted top, cute heels, or fancy sandals. It’s also from EHD’s newest favorite online shop, Tuckernuck.
Here’s a fuller shirt with such a cute paper bag waist! It also has pockets, as you can tell. Did we mention that it’s only $36??
This midi is a really fun easy one that not only has pockets but is high-waisted if that’s what you prefer:)
The long silk slip skirt is a trend that we do not find outrageous. It’s both casual but is so so easy to dress up. It’s a versatile piece.
Wearing a bubble skirt is a lot of fun. The back is smocked, but the comfort is maximum. The easy and playful design:)
As one of J.Crew’s bestsellers, I think it’s safe to say this one is pretty great. The polka dot is awesome but if you prefer a solid don’t worry, they have seven other colors to choose from!
Happy Comfortable Spring, y’all 🙂
*Unless Otherwise Noted, Photos by Kaitlin Green