How to Wear One Dress in any Weather

I’ve been curating my wardrobe for the past three years. My closet was full of experiments; sequins, gigantic heels, crazy cuts, and odd stitching. All of these have their time and place, but smashed together, they no longer fit the style I was going for (professional/chic – is she going to work, is she going to happy hour? Who knows!)

Ideally, I would start from scratch, donate everything, and go on an 80s music montage shopping spree. But that’s not how budgets work, so I had to phase things in and out slowly.

The biggest challenge was teaching myself new ways to wear what I already own. I started with pairing tops and bottoms that I’d never combined before, then got into the fun of layering dresses. That’s how I realized how flexible this floral shift is. The key to a flexible dress is:

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Minimal Skirt Swing

Some of these options involve tucking, so you want a compact skirt to avoid bunching.

High Neckline

This is optional, depending on what you want to wear under. Most shapes will work for button-ups and turtlenecks, but for crew or v-neck sweaters, you’ll want something that goes right over it.

Higher Hemline

I recommend a dress slightly above the knee. This is helpful for easy tucking and also makes the dress more like a tunic when you layer bottoms under.

No Waistline

By definition, shift dresses are essentially pillowcases with holes for your arms and head. A dress with stitching along the waist can limit your options.Do any of your dresses come to mind? If they do, scroll on down! If you’re missing this essential, don’t worry – I’ve picked out some great ones for you:

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Here’s how to wear it:

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When warm weather is around the corner, I get too excited and always end up chilly. For this look, I played it safe and layered a comfortable pair of drawstring pants over. Extra tip: I like to roll up the cuffs, but if you already have a pair of cropped pants, go for it. This will balance the look by not making your bottom half one continuous visual block.


Shifts work well with both heels and sandals, so you can wear them to any event depending on your accessories. It should also be lightweight for comfort in the heat and easy layering – a dress with too much of its own weight will not play well with other pieces.

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One of my favorite accessories are funky stockings. Not only do they look cool, they’re a great disguise for my unshaven fall legs ;). I top it off with a light neutral jacket and ground the look with solid ankle booties.


Like I said in my earlier post, I am not a fan of bulking up. The key to cold weather is layering under. I like to wear a neutral sweater, knitted tights, and (at least) knee-high boots. If you have a hot pair of over-the-knee boots like my friend Liz, break them out. (If you don’t, check out her awesome post for some inspiration).

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When the dress is a solid color, go with a patterned sweater. Winter tends to bring out the boring in our wardrobes, so try to have fun with it, I know I had a great time getting this post together – here are some more and accessory details!

Your Turn!

Leave a comment or tweet me:
Do you have any pieces you wear all year long?
Do you have something you want to wear all year long but haven’t figured out how yet?