If you want to ease into this look, start with a shirt-dress, which looks sort of like a tunic. You’ll get used to it and then go bold with a more feminine dress.

This is a fun, casual look that’s great for weekends.

Pick a color of shirt that goes well with your dress without distracting too much from it. Black or white shirts go well with most colors of dress. This is a great way to make your fun and skimpy bar-hopping dress day-appropriate.

Wearing a blazer with a dress will give the ensemble a slightly tougher, edgier look than if you wore a cardigan.

Try wearing your colorful fancy heels to spice up a gray outfit.

This works best for small thin scarves, not blanket scarves!

Pair this with jeans for a casual look, or with a flowy skirt for date night if that’s your thing.

Cuffing is a great way to show off stylish socks or ankle boots.

You could also just embrace the disheveled look of partially unrolled sleeves; many people claim this look is inspired by movie star James Dean.

This also works for oversized T-shirts. You can gather together some of the extra fabric at the bottom of the shirt and twist it into a knot. This will make the T-shirt more fitted, and is a quick, casual look.

Wear a colorful belt with your black jeans and tuck in a white T-shirt. Instantly your outfit looks more interesting! Big dangly earrings can instantly make your outfit look more formal and put-together. Wear your hair up if you really want to draw attention to your earrings. Accessories don’t have to be jewelry! If jewelry isn’t your thing, try wearing a watch, a scarf, a belt, a headband, or some fun, colorful socks.

You can also rub your jeans with sandpaper to give them that soft, lived-in feel. [12] X Research source

Lots of people like to cut their shorts at an angle, so that they are longer by the inner thigh and shorter at the outer thigh. [14] X Research source

Tailoring is a great way to still wear your favorite clothes if your body has changed in shape or size over the years.

Once you’ve dyed your shirt, take it out of the dye-bath, rinse it well, wash it in the washing machine, and hang it up to dry.