What goes with what
You own it. Now wear it.
Every page here takes one piece you probably own and gives you three outfits at different formality levels, plus the reason each one works. The reasoning matters more than the outfits, because it is what lets you apply the same logic to the next thing you buy.
What do you wear with cowboy boots?
Style cowboy boots with dresses, jeans and skirts. Compare how much shaft to show, try western details and choose comfortable combinations from your closet.
Read the answer →What do you wear with wide-leg jeans?
Three ways to wear wide-leg jeans with flats, sneakers and boots. Compare fitted and relaxed tops, and check the hem with your actual shoes.
Read the answer →What do you wear with a pleated midi skirt?
Wear a pleated midi skirt casually, at work or for an evening. Try different tops, shoes and layers, with practical movement and waistband checks.
Read the answer →How do you style a maxi dress?
Style a maxi dress with shoes and layers you own. Check hem clearance, try a knit over the dress and adapt the outfit for weather and the invitation.
Read the answer →What do you wear with a leather jacket?
Try a leather jacket over a dress or with tailored trousers. Compare texture, jacket length and comfortable layering without a universal waist-length rule.
Read the answer →How do you style a white button-down shirt?
Wear a white button-down for work, weekends or evening. Try it tucked, untucked or open, and check opacity and comfort with your existing clothes.
Read the answer →How do you wear a blazer casually without looking like you're going to work?
Style a blazer casually with jeans, a T-shirt, a dress or relaxed separates. Try your existing jacket and compare comfortable shoes, fit and layering.
Read the answer →What do you wear with knee-high boots?
Wear knee-high boots with skirts, dresses or trousers. Check shaft comfort and hem movement, and choose tights or a visible gap according to your preference.
Read the answer →How do you wear a slip dress during the day?
Three slip-dress outfits: a T-shirt and sneakers, an open shirt and sandals, or a fine knit with boots. Adapt the layers to your weather.
Read the answer →How do you style a trench coat?
Style a trench over jeans, office clothes or a dress. Try it open, tied or buckled, and check layer room and weather protection before heading out.
Read the answer →
Or just ask her
Every answer on this site is general. Style by Cher answers the same questions against the clothes actually hanging in your closet, which is the version that gets you out of the door. Free on the App Store for iPhone.
