When: On the weekend.

One of the advantages of being under 5'5" is that you can make a longer length piece of clothing work as two, such as a knit skirt or jeans.  The skirt above has a rather wide waist band which can be extended to work as the top section of a dress.  One thing to keep in mind when buying a dual functioning skirt is that the band fits snug enough around the waist, this ensures that it stays put on your upper half when used as a dress.  You could also use a belt if your are worried about the weight of the skirt pulling downward, such as I did here.  Another way to double your jean wardrobe is to buy a longer pair that can be worn with heels and then roll the cuffs to make 'crop' pants if you will, see how I did it here.  Do you have any items in your closet that work as two?  What are they and how do they work?  Tell me here!

Skirt as Dress: via Violette, $50
Sandals: Minnetonka 'Harriet' Sandal via Nordstrom Rack $30
Felt Clutch: Meow Meow, $10
Necklace: Target on clearance $7
Copper Bracelet: Vintage via 8th & Pearl Vintage, $44

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