This outfit formula is an acquired taste. Personally, I’m into the modern pairing and the outfit proportions and vibe that they create. If you wear skirts and sweatshirts (or hoodies), you might enjoy wearing them together. The skirt can be casual or dressy. If it’s a dressy skirt, you’re creating a modern juxtaposition in your outfit. If it’s a casual skirt, you’re simply combining it with another casual piece. Rugby tops can work as well as sweatshirts and hoodies, if that’s your preference.

I’ve had surprisingly great luck adding fashion sweatshirts to my wardrobe the last few seasons. Most are oversized and some are fluid. I like them because they’re 100% cotton, easy to launder, extremely comfortable against my fussy skin, work well in my climate, and are an effective way to dress down dressy trousers and big white pearls. Unexpectedly, I’ve amassed quite a collection.

The idea is to wear one of the five crew neck sweatshirts (not the hoodies) with one of my casual cotton skirts (below). It was recently warm enough to wear this combination and and I posted it on the forum. I LOVED wearing the outfit formula, and am excited to explore more options. Two of the sweatshirts are cropped, making them an easy pairing with skirts. The others have welts so they’ll work well un-tucked too.

Onto some outfit inspiration.

1. Black, White, Checks

A black and white flared and checked midaxi skirt with basque and pleats is combined with a light grey and black oversized printed sweatshirt. The black in both patterns unites them. It’s semi-tucked to showcase the waist and basque of the skirt, which creates some structure. The scrunched sleeves that showcase forearm skin also add structure. Black socks match the black in the outfit, while dressy white loafers match the white. Feel free to leave off the socks. Add a bag that works with the palette of the outfit.

Black, White, Checks

2. Columned

A column of colour is created by combining a casual black denim skirt with an oversized black hoodie. Black mules complete the outfit, creating a black look from head-to-toe. Use the same formula with any colour to create a long lean line. Add a bag that works with the outfit.

Columned

3. Playfully Pretty

A fluid patterned tomato red sweatshirt is combined with a classic pleated knee-length taupe skirt. Citron pumps add another colour and amp up the dressy. The animal print bag further amps up the dressy creating an effective Sporty Luxe look. I LOVE this outfit, and am much inspired by it. I have the exact same sweatshirt and a similar skirt. I’ll substitute the shoes for dressy gold flats or kitten heels, sport a citron bag, and add my pearls. In fact, I posted this exact outfit on the forum.

Playfully Pretty

4. Hard Edge

Last, a fluid grey and black patterned hoodie is combined with a dressier black knee length pencil skirt. It’s semi-tucked to showcase a black and silver grommet belt. A roomy black leather shacket tops the outfit. The hood of the top is worn outside the jacket like a collar. Dressy black heeled mules add the next dressy touch. Another smashing Sporty Luxe look. Add jewellery, handbag, eyewear, and watch as desired.

Hard Edge