3 Outfit Formulas: Taking Your Skirts + Dresses Into the Next Season

Every year when the hot weather fades and we slip into the colder months, I daydream about the outfits I’m going to wear. And even though jeans are my *very favorite* thing, I always find myself enamored with cold-weather looks that center around skirts and dresses. And I swear to myself I’ll do more than live in jeans all winter. (Though that’s a fabulous option too.) The best evidence of this is my extensive tights collection that is a nod to my winter aspirations.

I declare: this year will be different!

Right now, I feel extra motivated (might be a creative reaction to these hard times), so I brainstormed a few formulas. It gave me a good excuse to play dress up and see which of my skirts and dresses would be good options for the colder months. And, more importantly, for this blog post, it gave me a chance to see how to experiment with making the outfits work – stylistically and weather-wise.

Here is what I came up with.

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1 // Add a cropped sweatshirt and boots

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This seems like a no-brainer, just add a sweatshirt and boots. BUT, the shape of the sweatshirt goes a long way to impact the outfit, particularly if you’re putting it on over a dress. I found a cropped sweatshirt (like above) makes for really easy styling. The second easiest type is a sweatshirt with a tight waistband. This helps you pull it up a little bit to create a visual waistline over your dress. OR you can simply front tuck into a skirt. Some people have suggested using a hidden belt or tucking into your bra, but both of those methods feel a little fussy for my preference.

I opted for casual and chunky boots to contrast with the shiny, fitted style of this skirt. But I think any flat boots could work. I prefer boots that are fitted at the ankle (instead of loose) because it works with my leg shape in a way that I like. Everyone is different, and knowing what you like best and what works well goes a long way to make outfit building more efficient.

OUTFIT DETAILS:
Heavy Fleece Mockneck Pullover (M) in beige
Skirt, sold out (very similar here and here)
Park Boots (41), Dear Frances (these are spendy, but there seems to be frequent coupon codes!)
Ama Earrings, c/o Seaworth (use code SEA&SALT to save 15%) –> I love a bold, gold earring with a casual outfit!
Circle Bag (similar)

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2 // Style with a chunky cardigan and tights

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When I bought this skirt I had every intention of taking it from fall to summer because the color is one of my very favorites. What I didn’t anticipate was how easy it would be! The shorter length makes it a great candidate for tights because it balances out the ‘covered up’ factor that often comes from tights. (Similar to the covered-up factor that comes from covered ankles.) The look would be entirely different if the skirt was to my knees or longer.

The chunky cardigan was the easy option for this outfit, and it kept the color palette neutral, which I like when layering. A turtleneck would work with this outfit too, or a chunky pullover, or my favorite – these alpaca sweaters. I also tried this with a flannel shirt and it was really cute.

A note on tights: Getting them on always feels like a pain, but once they’re up, they feel quite good. This particular pair was gifted to me last year from Sheertex, and I’m a convert. They make them out of a special *unbreakable* material. I like them because they’re just the right amount of sheerness/opaqueness. They don’t go too far in either direction. I also have a pair of fleece-lined tights and those are great for the coldest of days.

OUTFIT DETAILS:
Texture Cardigan (M), Everlane
Skirt (6), sold out in brown, but available in 2 other colors
Classic Sheers in black, c/o Sheertex
Park Boots (41), Dear Frances

3 // Layer underneath a sleeveless dress

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This one feels like the oldest trick in the book and I suppose that makes it ‘tried and true.’ I adore the look of the turtleneck and pinafore together. This would also work fabulously with a slip dress or almost any sleeveless summer dress. I styled a linen dress and a white turtleneck a couple of times and loved it. The trick is to make sure you can style and balance the summer aspect of the dress in a way that makes you satisfied with your outfit. Some fabrics or shapes can be harder to transition to fall. For example, a poplin or thin cotton would need more base layers. Or a full and long dress might look too imbalanced with a bulky warm layer on top. The key is to keep trying until you get a combination that feels just right.

I’ve said this many times before: a little brainstorming ahead of time is often really fruitful for creating outfits you love. Sometimes working outside of ‘in the moment’ (especially if you’re dripping wet from the shower!) can help you be more creative.

I chose these boots again, for my third outfit, because I super-duper love them. They are so comfortable! And they also feel a tad edgy, which is just what a sweet pinafore calls for!

OUTFIT DETAILS:
Model No. 32 the Pinafore in Black Linen, S, c/o Pyne & Smith, from our spring partnership
Merino Turtleneck (M), c/o
Park Boots (41), Dear Frances
Half Moon Bag, A.P.C.

Thanks so much for reading along! Happy styling! xx

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