Q: I would like tips on wearing women's boots/booties during the summer.
A: I'm all in favor of year-round boot wear, but know it can be challenging to style this family of footwear for warm weather.
If you're pairing ankle boots with slim or skinny pants, try rolling a small cuff that hits just above the boot top, exposing a sliver of ankle. This provides a peek at the true silhouette of your leg, and also makes your overall look feel more seasonally appropriate. If you're doing a dress or skirt and worry about visually shortening your legs, opt for a bootie that's close to the color of your skin tone. Also accept that your eye may still be adjusting; ankle boots are still relatively new, and many of us aren't used to seeing them worn with bare legs.
In terms of taller boots for spring and summer, I'd advise opting for light colors regardless of your skin tone. Knee-high black boots against bare skin won't look terribly seasonal, but knee-high tan or cognac boots will be less jarring. Styling tall boots with cowgirl-influenced looks helps ease them into summer wear, too. Try a snap-front shirt and denim skirt, or floaty white dress and denim jacket.
Q: Tricks for working with extremely pale skin. I'm very fair — to the point where when I go without makeup, total strangers ask if I'm not feeling well. I've adopted the strategy of playing up my paleness rather than hiding it, but would always be happy for more tips.
A: I'm right there with you, my pale friend. I might not have the Scandinavian ancestry to back it up, but I rock Casper-white skin every day of my life.
First and foremost, my advice would be try not to worry about it. Anyone who has the time and energy to police the shade of your skin should really get a hobby. Your skin is your business, no matter how tan, not tan, pale, dark, spotty or covered in "Twilight"-reminiscent glittery bits it may be. Period.
Aside from that, try mixing more prints and patterns into your looks, especially up top. Big swaths of color can wash you out or alter how your skin tone is perceived, but patterns are more forgiving. Naturally, some patterns will work better than others with your hair, facial features and figure, so choose carefully. But be aware that doing patterns against pale skin may appear less harsh than solids.