Silk Midi Skirts + T-Shirts: 5 Ways To Style This Early Fall Outfit Idea

We Facetimed with R the other night – he’s away at college for the first time (sob!). He looked happy and well-rested which is honestly all I can ask for. He also looked cuuuute. His cheeks were a little flushed from the cold, and he was wear a cozy wool(!!) sweater. We’re all still basically sweltering down here in Philly, but it made me hopeful that actual fall is on its way!

Until then, of course, I’m on the hunt for a few early fall outfit formulas that handle warm weather from 11AM – 2PM…and then can easily be layered up for our slightly cooler mornings and evenings. One of my favorite, most tried-and-true early fall outfits involves some sort of silky midi skirt. They’re not as covered-up as jeans, but not as leggy as shorts, either.

skirt (m) – on sale! | flats

My one stipulation, however, is that these skirts must be styled casually for everyday wear. And while I love them in the winter with oversized sweaters (this one, in particular)…right now, all I want are silky midis and t-shirts.

The 7 Ways I’m Wearing Silky Midis With T-Shirts This Fall

So here’s the thing: my pet peeve is when magazines (or blogs or whatever) promise to style up, say, a t-shirt and jeans multiple ways and then they basically cover up the t-shirt with sweaters and jackets and whatever else, leaving the base outfit (tshirt & jeans) looking…boring.

I’m styling up t-shirts and midi skirts because I actually want to wear a t-shirt and a midi skirt. It’s hot during the day – I don’t want a cute outfit that relies on layers, I need this base outfit to stand on its own.

So here are 5 ways that I’m using t-shirts of all kinds (fitted, oversized, v-neck, graphic, etc) to style up my old silky midi skirt. You can add a jacket or oversized sweater to any of these outfits, but I wanted to make sure that each could stand on its own.

Outfit 1: Silky Midis + Oversized, Untucked Tees

tee – one of Pax’s Vans tees | skirt (m) – on sale! | flats | bag – or similar | necklace

For an oversized, untucked tee (I love big ol’ graphic tees, stolen from my guys, haha), the key here is that the rest of the accessories have to look VERY intentional. In general, I think in threes, meaning there’s gotta be at least three intentional pieces, in addition to the outfit itself. Here’s the formula that’s working for me:

1. Ballet flats – these are the only shoes polished enough (or maybe ladylike enough??) to bridge between the fancier skirt and boyish top. I love a good statement pair, but any would work.
2. Obvious jewelry – my pearl-and-leather necklace is another good bridge of girly & tough
3. A nice bag

For a slight twist on this same outfit idea (but maybe one better suited to slightly cooler weather)…swap the t-shirt out for a long-sleeve tee and add boots.

tee (s) | skirt (m) – on sale! | boots | bag | ring

Same rule of three applies:

1. Nice boots
2. Ladylike bag
3. Cocktail ring

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Outfit 2: Tuck In The Tee

tee (s) | skirt (m) | boots | bag | ring

Tucking stuff into silky midi skirts doesn’t always work, but if your tee is that magical length/thickness, it does result in a more polished (yet still casual!!) look. I swapped the ladylike bag out for my work bag, but it’s still chic enough to elevate the look (along with the boots and jewelry).

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Outfit 3: Turn Your Oversized, Long-Sleeve Tee Into A Pretty, Ruched Top

tee (s) – same tee, different color | skirt (m) | boots | bag | ring | bracelets

Sometimes these oversized tees just need a little shape. Adding matching stretchy bracelets to each arm can create the feeling of long, puffed sleeves, and if you have a hair tie and a quarter, you can easily put some ruching anywhere in your tee (I like mine just above one hip).

(The quarter goes on the outside of the tee, the hair tie wraps around it from the inside.)

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Outfit 4: Layer A Tee Over A Collared, Button-Up Shirt

tee (m) | button-up (old) | skirt (m) | boots | bag | ring

This is nothing new – I’ve been doing this trick since the 90’s haha – but I sometimes need a reminder. This trick works especially well if you have a t-shirt in a plain color. The only tricky part is that the tee has to fit somewhat looser than the button-down shirt underneath it.

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Outfit 5: Try A Sporty Tee + Sneakerinas

tee (m) – on sale! | skirt (m) | sneakerinas – on sale! | bag | necklace (on sale!) | ring – coming soon!

Any sort of sporty tee – rugby stripes, baseball tees, even rugbys themselves – can look good with silky midi skirts if they’re balanced by a shoe that also bridges the gap between the sportiness of the tee and the ladylike nature of the skirt. Sneaker ballet flats (or sneakerinas) area freaking perfect for this.

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Outfit 6: A Baby Tee + Cool Accessories

tee (m) | skirt (m) | ballet flats | bag | ring & earrings – coming soon!

The advantage to these slightly shrunken tees (although, I’m still buying mine a size up) is that they’re meant to be untucked. The rules of three still apply, however:

• Major jewelry
• Ladylike bag
• Ballet flats

A few notes: those baby blue ballet flats are bananas soft and comfortable – I applaud you, Reformation. And I like how the skirt and shoes are both lighter…even if they don’t exactly match. The idea of dark tee + dark bag…and light skirt + light shoes is totally working.

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Outfit 7: Dress It All Up With A Classic White Tee

tee (s) | skirt (m) | heels | bag – vintage | ring | earrings – old

If you have one of those classic white tees that are perfect (not too thin, but not opaque), you can both tuck it into the skirt AND decorate it up. Wear a black bra underneath – I find it a much cooler look and somehow more flattering than a truly no-show bra under a white tee.

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xo,

S