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A Spring Transition Outfit Idea I’m Loving – Maxi Skirts FTW

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 is what she does (that I fully copy).

Jean Jacket (similar) | T-Shirt | Skirt | Boots

  1. 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). Again, this could be a vintage t-shirt or a ripped sweatshirt. Sure you can wear a ruffly blouse with this skirt, but that looks more formal, less every day (IMHO). 
  2. THEN, Front tuck that top. You want to see the waistline so it’s a tad bit more defined. 
  3. 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. Keep it casual and a little messy/masculine on top (or a simple muscle or ribbed tank will do) and then easy breezy and full/ruffly on the bottom. Add a baseball hat for the full “I’m a celebrity that is trying to not get noticed in Erewhon” effect. Lol. 

Here is the effortlessly cool Suzanne who helped style the two of us for a fashion shoot a handful of years ago. How cute yet easy is that outfit?! Casual Top + Fun Skirt + “Wrong Shoe” = A cool and comfortable look.

Sweatshirt (similar) | Skirt | Sandals

This is the outfit I was referring to in the intro and boy was I comfortable:)

from: on the hunt for comfy and cute spring break sandals – here Is what I found

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! Think how cute this would still be with a pair of Converse or boots.

My team curated a bunch of skirts should you be into this transitional vibe (hopefully you have something in your closet already). And for those of you/us who still like a little lift, I love my New Balances with the light platform or go for a platform slide (like this one) or Teva

Wave Denim Maxi Skirt

This one may not be super flowy but it is wavy:) The details of this skirt are so cool and honestly, it does look pretty comfortable. Plus, it’s from Farm Rio which we can attest for their awesome quality.

Linen-Blend Tiered Midi Skirt

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. It also comes in other patterns and colors too!

Gwyneth Slip Skirt

How great is that bold yet casual stripe? The linen fabric is so pretty and versatile.

The Linen Wrap Skirt

Another neutral but bold patterned skirt! That extra-long tie is also very cool and think how fun this would be paired with a vintage band shirt and leather jacket??

Elevated Embroidered Maxi Skirt

Talk about a whimsical spring skirt! It not only has an eyelet trim but it has a lace section too. Beautiful and easy to throw on with a fun crewneck sweatshirt!

Green Margarita Skirt

Another more slender option but that print is so chic and playful! Just think, during the day throw on a slouchy t-shirt with comfy shoes, then at night dress it up with something more fitted and a cute heel or fancy sandal. It’s also from EHD’s newest favorite online shop, Tuckernuck.

Linen Tie-Front Maxi Skirt

Here’s a fuller shirt with such a cute paper bag waist! Plus, as you can see it has pockets. Did we mention that it’s only $36??

Petra Linen Midi Skirt

This midi is a really fun easy one that not only has pockets but is high-waisted if that’s what you prefer:)

The Tilda Maxi Slip Skirt

Something that we are not mad that is trending is the long silk slip skirt. It’s both casual but is so so easy to dress up. A piece that is good all year long.

Bubble Bliss Skirt

The idea of wearing a long bubble skirt sounds pretty freaking fun! This one also has a smocked back but maximum comfort. Effortless and playful:)

Gwyneth Slip Skirt

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

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1 month ago

this may convince me to finally go maxi. Shout out to Garnet Hill’s long skirt, a favorite for many years and now available in knee length as well— good New Hampshire-based company:—black-driftwood-floral/clothing/categories/skirts/334123?listIndex=6&defattrib=Color&defattribvalue=DRWD&uniqueId=334123_color1&isNewProduct=false&newItemBadge=true

1 month ago
Reply to  Colleen

I own that Garnet Hill skirt. It’s so good!

1 month ago

I am going to try this with my all-time favorite bargain hoodie, the Hanes EcoSmart Women’s Full-Zip Fleece Hoodie.

1 month ago

Just want to add that I tried on that Faem Rio skirt at Nordstrom and was pretty disappointed that those waves are cut on both sides. Meaning it’s super easy to pull apart and create a modesty issue. At this price point they should have included extra material to allow for things like walking and sitting. It all other ways it felt like good quality, so by all means try it on. But it was a no go for me.

1 month ago
Reply to  Michelle

Do you mean on the button placket?

1 month ago

Please please please bring back more Suzanne. Her “effortless” (I know it’s not) cool is the stuff dreams are made of!

1 month ago

Wish I was a skirt person! I’m a jeans gal 😊. Sorry to be so off topic, but I snoozed and lost on the EHD rugs USA collab, and now the Oregon Plaid Beige rug of my dreams is out of stock. I see a lot of them are. Any word on when these gorgeous rugs will be back in stock? Thanks Emily and team!

1 month ago

can you pretty please do a roundup of cool graphic tees that are fitted not so boxy?

1 month ago
Reply to  Jules

Check out Sub_Urban RIOT (or search Suburban Riot). Lots of cute options.

1 month ago
Reply to  Jules

Yes! I’m really intrigued by this outfit formula but I’m always struggling lately with tops lately, everything is either too boxy, too tight, or too cropped!

1 month ago

Great Idea for me delicious recipe!

1 month ago

Emily’s Birks are the Milano in cognac, amiright? The link brings us to the big buckled version sans back strap.

1 month ago

Aw, I love Emily’s voice. I’m going to say it again and again! (Cute ideas, too. I will have to try.)