i'll start with questions that were asked in the comments:
Q: How can I style cute clothes and professional outfits without wearing heels? -- Sharon
A: this is a great question! although i've turned into a heel and wedge lover, before about 2 years ago i maybe owned one pair of shoes that weren't flats. my entire senior year of high school i wore a pair of gold ballet flats that i bought at Target. my entire year. so i totally understand your desire to create cute and professional looks without heels. one option is to buy a pair of really nice looking flats, maybe with some sort of embellishment that dresses them up (1) a bit or a pointed toe (2). i also really like loafers (3) as an alternative to regular flats. they're the type of shoe that can be dressed up or down. if you spend a lot of time on your feet and can't wear flats without support, look for some that have a built-in wedge (4) or have a slight wedge and peep-toe(5).
A: i'm the queen of jeans and a plain tee. i have at least 15 plain v necks in my closet from J Crew Factory that are on rotation. if you feel like jeans and a plain tee is too casual, try adding some jewelry or cute flats/sandals to make it look like you actually thought about your outfit that day instead of just throwing things on. for alternatives, try a cute sundress (like this one from Old Navy), a maxi dress, colored denim (which you can wear with your plain tees and not feel frumpy), or a cute patterned top with jeans. your solution could be as simple as just changing one item to make you feel less frumpy and more put together!
Q: How often do you clean out your closet? Either to change seasons (do you do this?) or give away things that you no longer like/fit? I know I don't do it as often as I should and have a lot of clothes taking up space in my closet that I'm going to "wear someday". -- Maddy
A: i do a full closet clean out every 3-4 months. which means that i take just about everything out of my closet, try it on, and decide if i want to keep it or not. if i haven't worn in it the last 3 months, i get rid of it because it's just taking up space and i know i won't wear it in the future. i also kind of clean out as i'm going along. sometimes when i'm looking for something to wear, i'll come across a top that i can't remember wearing in the past 2-3 months and then i get rid of it. i'm not much for hoarding clothes, so i like to just purge and get rid of what i know i'm not going to wear. (shameless plug: i have an instagram account for clothes that i sell @laurenelizabethcloset). i think everyone should clean out at least every 6 months. you can even do a clothes swap with some of your girlfriends to get rid of your things and maybe add some new pieces!
Q: This is such an odd question, but when I buy pencil skirts, the slit in the back is stitched at the bottom, but there is still an opening. My mother told me you're supposed to cut out the seam so the slit is completely open. Do you know anything about this? -- Mara
A: listen to your mama! she's right, you should always cut the stitching out that can be found at the bottom of a slit on a pencil skirt, dress, or blazer!
Q: Any tips to dress down work tops so I can wear them with jeans and not look overdressed compared to everyone else? -- Kalie
A: it's hard to fully answer this question because i don't know how dressy your work tops are, but i'm using a fairly plain silk blouse in my example. the easiest way to dress down a fancy top is to change your bottoms - either throw on some patterned shorts, colored denim, or slightly distressed jeans. that will quickly make your look more casual without too much work. you can also choose to go with a simple flat or sandal, or accessorize with a fedora or casual scarf (if it's chilly). also, switching to a cross-body or hobo bag can bring down the dressy a bit.
Q: Does horizontal chevron make you look wider like horizontal stripes? Is chevron still "in"?
A: i'm inclined to say that it would probably have a widening effect, like stripes do. i don't think chevron is quite "out" yet, but i definitely think it had it's heyday and we're moved on to florals it seems.
Q: What can I pair with a black maxi skirt? I'm stuck in a white tee rut! - Jen
A: oh, Jen! the possibilities are endless! i love maxi skirts for that reason. and they're ridiculously comfortable. you can go with a great patterned tee (1), which you can tuck in or belt it. i love wearing my maxi with a good graphic tee (2) like this one. also, i feel like i need that tee. another good option is a denim or chambray button up (3). for a more casual look, you can do a loose-fitting tank (4). i have a great grey one that i wear with my skirt a lot. i tuck it in so it's not total frumpsville, though. if you want to dress it up a bit, throw on a lace top (5) or layer the lace top over a colored cami. finally, if you just want to stick with the tee, pick a different color or one that has a pocket (6) or subtle pattern to change it up a bit!