1. I'm ready to invest in a nice leather bag that I promise to take good care of. Any advice on how to pick one out that is timeless and not too trendy?
We totally get that the word "invest" means different things to different people, whether it's spending $50 on one item or $1,000. However, we think that if you're going to get a new leather bag that'll actually last you, you should be ready to drop at least $100. Brands aren't terribly important, but quality definitely is: You want a bag made of leather that'll look better with wear, and not worse.
So, your first piece of evidence should be which types of vintage designer bags you love the look of (Coach, Louis Vuitton, and Dooney & Burke are all solid choices). In terms of shape and size, you'll want something that's big enough to actually fit your essentials, plus room for some extras, but not so big that it weighs you down. We'd also avoid getting a bag with too much emphasis on the hardware — off-trend studs, spikes, rivets, and embellishments are the quickest way to date a bag.
2. I can't bear to wear the same old rainboots during the summer (so sweaty!). Is there another way to dodge the puddles in a stylish way?
If your shoes are strictly for commuting (meaning, you have another pair of shoes ready for you at your workplace), you can't really go wrong with a pair of short rainboots (Loeffler Randall makes some lovely versions). As long as you size up and wear them with socks, you shouldn't feel overheated.
However, if these are shoes that'll need to last you all day, you're also in luck. There are tons of jelly sandals and flats that range from cutesy to professional, and most ring in under $100. Find one with a thicker sole and a closed toe to minimize in-shoe slippage.
Melissa For J. CrewT-Strap Sandals, $70, available atJ. Crew.
3. Quick! I need a suit for an interview. What's a budget version that I'll be able to wear again and again and in loads of different ways?
Suits are expensive, and there really isn't a way around them. It might be a tough reality to swallow, but expect to spend at least $100 on a suit set that you'll be able to wear again long after you've scored the job. When looking for a suit, be sure to make sure that you're buying the full set; even expensive suits can look cheap if the colors don't exactly match.
As for style, don't veer too trendy: Stick to a two-button blazer, and a high-waisted skirt or a slim-leg, cropped trouser (save those short suits and wide-leg styles for when you get your first bonus!). As long as the shoulders fit, the silhouette just grazes your body (not too tight or too loose!), you can have the lengths tailored pretty cheaply. Afterward, the blazer and bottom can be worn separately in a zillion different, office-appropriate ways. As for retailers, we're big fans of Express' suiting section for affordable pieces that won't make you look like a '90s telemarketer.
Express One Button Jacket, $98, available at Express.
4. What exactly ARE you supposed to wear under a paper-thin T-shirt?
Though you may be covered up, a paper-thin tee still presents some challenges in terms of modesty, especially when it comes to what bra you're supposed to wear them with. A regular underwire bra can feel a bit to revealing, but we love how chic a fashion-forward sports bra looks underneath a thin tee. Not into showing that much skin? A skin-tight black camisole can also do the trick.
Helmut Lang Threadbare Tee, $125, available at Helmut Lang; Helmut Lang Micro Modal Asymmetrical Bra, $90, available at Helmut Lang.
5. My office is freezing, and I need a cardigan to keep at my desk. What's something that's cozy and goes with everything but still looks professional?
Since your office climate is pretty much static during the summer (read: permanently freezing), you'll need a cardigan that'll go with absolutely everything you own without attracting too much attention. What that means? A black or gray cardigan that hits you at mid-tush in a weave that won't pill, won't pull, and is thick enough where it won't show every tuck and fold of your shirt. In this case, cashmere is really our go-to, and this cardigan from Tory Burch is basically completely neutral in terms of style…a good thing, in this case.
Tory Burch Miranda Cardigan, $295, available at Tory Burch.
6. I have no idea what to wear with those boyfriend jeans. Help!
The key to making boyfriend jeans work is all in the ankle. Either make sure they're already cropped or give 'em a roll — it's very important that they end at the very slimmest part of your ankle. Now, the safest way to wear them is to pair them with stiletto-thin heels (either pumps or strappy sandals), but we love how cool a chunky platform sandal looks with them as well.
If you've gone girly on the bottom, feel free to wear an oversized oxford, boxy tee, or another tomboyish top (tuck it in to make it feel more polished!). If you want to wear something tighter and more feminine on top, wear a low-cut, lace-up shoe or sandal to counter the sweetness.
The sad fact of the matter is that not all "nude" heels are created equal. While there are tons and tons of options for the lighter end of the spectrum, darker skinned girls don't have the same luxury of choice. It's a bummer and totally unfair, and we hope that designers start catching on to this fact (ahem, ahem).
That said, darker toned nude heels can be found, and the easiest way to track them down is to use a shopping service like Polyvore or Shopstyle, which lets you filter by item color. Just select the hue you're looking for and style of shoe you want (patent pump, platform sandal, etc), and you're on your way! For a guaranteed find, we like Nine West for its wide selection of simple heels in the full nude spectrum.
Boutique 9 Justine Heel, $89.99, available at Piperlime.
8. Are leather shorts ever worth it? They look so cute, but I can't imagine how hot I'd get in them.
if your climate involves 100+ temperatures and unrelenting sun, we can't responsibly advise you to get leather shorts lest you want to melt into a puddle. But, we can definitely vouch for a leather — or leather-look — short during the summer, for its ability to make a simple T-shirt look like so much more. The key is to pick a short with some room to move — anything too tight, and you'll be sweating the whole day. A perforated version in a lighter-weight faux leather is our Holy Grail.
10 Crosby Derek Lam Shorts, $195, available at Shopbop.
9. Okay. You guys have convinced me. I'm going to go out this weekend and try on a pair of overalls. But…what am I supposed to wear on top?
There's actually quite a lot you can wear with overalls on top, from body-hugging crop tops to free-flowing blouses. We'd avoid going too thin in the straps (that's a '90s throwback we don't want to live through again) or too elaborate with ruffles, but anything in a streamlined, simple shape will work. Go wild with the prints though! It'll help keep things looking modern…and prevent anyone from telling you that you look like a farmer in those clothes...
Current/Elliott Ranch Hand Overalls, $368, available at Anthropologie.
10. I know that "fashion" sneakers are a thing, but they still look like gym shoes to me. What's the trick to picking out a pair of running shoes that works for real life, too?
Two things contribute to how "fashion-y" a sneaker is: what shape it's in and what outfit you're wearing it with. There are a few styles that are popular with the fashion set right now, and they work in nearly every colorway: Nike Frees, Nike Flyknits, and New Balance 501s are all safe picks. The key is to find a not-too-puffy silhouette in fashion-forward colors like neons, pastels, corals, and grays (a white sole also helps temper the shoe).
When it comes to wearing them in real life, it's important to let your ankles show, so cropped trousers, rolled-up jeans, and short skirts, shorts, and dresses all work. Avoid wearing anything too casual like leggings or baggy sweats — your sneakers won't look as intentional.
Nike Rosherun Black/White Sneakers, $118.79, available at ASOS.
11. I want to wear a backless dress but I'd rather not go braless. Are there any solutions?
Depending on your bra size, there are some fancy — but pretty uncomfortable — bra options that let you lower your bra strap to the small of your back (there are also stick-on bras, but we've never had much success with them staying on during the summertime). However, these aren't as supportive as regular bras, so these definitely aren't a solution to those of us who are fuller on top. However, for smaller chested girls, a convertible, low-backed bra can provide some support while keeping the back of your dress clear.
Le Mystere Convertible Underwire Bra, $65, available at Saks.
12. I'm pretty short but I love ankle-strap heels. What can I wear to elongate my leg?
Ankle-strap heels are a godsend — they allow us to get to skyscraper-tall heights without making us feel like we're slacklining. However, if you need all the help you can get in the leggy department, there's only one option: go short and go high. High-waisted short shorts, skirts, and dresses are really the only way to keep that leg line looking long. Match it with a slim-fit, longer vest, like Wendy did, and you'll be able to make those short hemlines look way more professional.
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As people who talk, touch, and think about fashion all day long, it's kind of our job to have an answer for anything clothing-related. And, as you can imagine, we've also become de facto Dear Abbys for fielding our non-industry friends' shopping questions. Here's the thing: Real-life shopping problems offer budget, cultural, and weather restrictions in a way that makes for a much more interesting challenge than, say, "What would you wear to the Met Ball if you had a million dollars and were BFFs with Tisci?"
So, as summer gets into full swing and a new season inspires some serious shopping trips, we've rounded up some of the most common quandaries we've been getting from you all via Facebook, Twitter, text, and hollers. Click through for 12 of your burning shopping questions and our responses, ahead.