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Help!  I need ideas for organizing all the shoes in my closet!
TB
TTL says:

First, I’d say see what kind of purging you can do.  Think there are some pairs you can live without? Haul those over to your local resale shop (I like Crossroads or The Real Real for designer brands) and free up some room in your closet to buy something new with the extra dough you just made!

Next, check out Ikea! I bought two of these in glossy white, various sizes and stacked them sideways at the back of a hallway closet.  They fit about 4 pairs per block, if you do two in front, two in back and then stagger them with their heels/toes facing forwards and back (this also helps you when you’re looking for a specific pair too).  You can also use simple shelves too. I just used these for a laundry room project.  My suggestion would be to put a few of them up at the top of your closet (where nothing else lives and space is just wasting) then grab yourself a foot stool!  Just make sure when picking out shelves that they’ll be deep enough to store your shoes the way you want to.  I’ve also seen these used in narrow spaces where two are placed close together in a V shape (so that each shelf holds a pair and the toes of each touch each other in the middle of the V) and then this pattern is repeated up the wall.  For all of the above, unless you are suuuuper proud of your collection, I’m not a huge fan of displaying shoes out in the open, so I’d keep all of these inside a closet, if you have the space.

If I were to invest in 4-5 key pieces for my wardrobe, what should they be?
TA
TTL says:
– A black structured bag.  You need something you can wear to the office (with your laptop), on a fancy date, drinks with the girls and at the airport.  I like this, thisthis, this, this or this.
– The perfect nude and black pumps (plan to resole and repair!). Check out these, these, these, these and these.
– A blazer.  A wedding, a funeral, the office, the bar. I like this, this and this.
– Evening clutch.  Some favorites here, here, here and here.
– The perfect LBD.  I don’t mind one with a little twist.  Try this, this, this and this.
Runners up:
– Good denim.  I like to grab the trendy stuff on sale at Urban Outfitters or from the $12.99 pile at Forever 21, but it’s nice to have a good pair you know will last you a while (although, I’ll still try to find it on sale at the Rack).  I’d opt for a darker wash, like these, a comfortable medium rise and a nicely tapered leg and definitely no pocket embellishments.  A few more here, here and here.
– A white blouse (or 4).  I like this, this and this.
And by “invest,” it might not need to be money, it could be time.  Make the effort to get things tailored perfectly, and they’ll always be in style.
 
How do you choose and wear a white collared shirt and look put together vs. frumpy?
JC
TTL says:

Check out some of the white blouses I’ve linked above and a few more here, here and here. The key here is fit.  You want something that isn’t too loose (unless you’re going for a boxy or boyfriend look), but doesn’t explode at the buttons when you put on a real bra.  I find that a neat and clean short collar makes for an extra polished look, as do larger, crisp cuffs.  A well fit poplin shirt can be layered under anything, but if you want something more feminine, don’t forget silk.  I love a good neck embellishment or tie too.

How do I know if I can trust a shopping site? I often see items on blogs that are very cute, but the site seems sketchy, any surefire ways to tell it’s safe to buy?
TA
TTL says:
Honestly, I’m probably not the best person to be giving advice on this, because I’m pretty trusting when it comes to shopping online and that’s likely not the best policy.   If I am fairly familiar with a blogger who has shopped there, then I usually trust the site.  Personally, I’m less concerned if the site is a scam and more with how accurate the items will be.  Lots of these sites are peddling look-a-like stuff that’s being churned out in bulk in China.  With that assumption, I buy based on whether I can stand the thing taking a million years to arrive and then being disappointed with it (which, in my experience happens about 1/3 of the time).  If I can handle that possibility, I usually go for it knowing that if it works out, it will be worth the risk.
Examples of places like this, that I would shop (but still with caution) are: SheIn, ChicWish, Front Row Shop, YesStyle and Choies.
But, I can totally understand if most other shoppers would decide to be more conservative than I.
How do I dress up the standard fall wardrobe (i.e. jeans and a sweater) to make it look a little more “going out” appropriate?
TA
TTL says:
Heels! I find that most of the time, adding a pair of fancy shoes or fun ankle boots, even if you feel like they don’t go with a casual outfit, can really jazz up an ensemble and make a fun combo for hitting the town.  Some options here, here, here, here and here.
If you’re not into amping up the height just to go out, I would make sure your outfit has at least one really “of-the-moment” trend.  So you don’t have to go 100% all off-duty-model, but just add one current fashion-mag worthy element. Some examples: velvet, cropped jeans, a choker, high waisted pants, a bodysuit or culottes.
What types of “everyday” earrings are IN?
TA
TTL says:
I am not an earring person, so my answer is going to be that you don’t need any.  But I get that some people are earring people.  For those of you, I would choose something delicate with a little bit of interest like this, or maybe something geometrical, like this. You want something that elicits a, “Oh, I like your earrings” about five minutes into a conversation and not, “Whoa, I want to swing on your chandelieeeeeeeers!” from 20 feet away.
What are some tips/options for breaking the “athleisure” habit?
KR
TTL says:
First, why?  I love the athleisure look!  But, I get it, when you dress for comfort, you’re playing with fire. It’s quite the slippery slope.  You might end up looking more like a mom who’s kids are late for school and therefore did not have time to change out of her pajamas.  Or, you’re wearing “athletic” gear but it’s not exactly current, flattering or in good condition.  Just like you would when deciding what to wear out on date night or to a friend’s wedding – stay up to date on the trend and make conscious decisions rather than habitual ones.  Or better yet, make a new habit!  Here are some super cute options: fun leggings like these or these, easy pants in an on-trend color, a new kind of sweatshirt and how about something fun and strappy to stick out of an even more fun top.  I think the key is to think, “On my way to a trendy yoga class…” rather than “Just got finished with a run with my high school track team and then painted the house.”
But, if you really don’t want to be known for never putting on real pants, you’ve got to change your game plan to something that will stick.  Working from home, it was easy for me to fall into the leggings-and-oversized-sweater trap.  Don’t get me wrong, that’s a perfectly acceptable casual look, but once your husband suggests that the dog won’t recognize you when you’re wearing bottoms with a zipper or buttons, then you might want to switch things up a bit.  I found my comfortable alternatives and made them the easiest things to access in my closest.  My go-tos are these culottes, these super stretchy jeans in black (I ripped the knees open on and cropped at the ankle), a loose tee paired with a fun triangle bra (both super high on the comfort scale), and a chunky knit for cooler temps.  Paired with comfortable flats (see post below!), high-top sneakers or funky ankle boots, sometimes I feel downright cute walking the dog!
Should I toss my colored jeans?
TA
TTL says:
For the most part, yes.  I’d say keep anything neutral or white and maybe even the most lovable fall color, burgundy, but other than that, I would think you could probably use the closet space.  Pro tip: take your gently loved stuff to Crossroads and at least try to get something for them.  A little extra pocket change never hurt anyone!
Flats. They are either comfortable and look like they were designed for a pre-teen OR still not that cute and feel like torture. So I guess the question is how do you get through a professional day without having to wear four-inch heels?
KR
TTL says:
For quite some time, I thought I needed to be wearing heels at the office.  I love the way they make you stand up straighter, look slimmer in just about anything you’re wearing and walk with a little bit of authority.  I had some gorgeous pairs, but then they started completely deforming my feet and were a total pain (literally).  Plus, I just got tired of them.  So, I had to start thinking long and hard about flats.  I really, really dislike a blah flat – just as much as a blah pantsuit or anything else women have begun to settle for in order to be comfortable and “appropriate.”  Business casual is like a danger-zone, soul-sucking, black hole for a lot of women.  It’s a scary place and my insides hurt a little bit to think about when I used to be stuck there.  There is hope, though. A little bit of thoughtfulness goes a long way to not letting yourself fade into blahhhhhh.  I’ve got plenty of adorable flats on my wishlist right now, which I’ll share below.  I would say the best way to stay on top of it though is to keep a constant eye on celeb fashion (they’re not always in heels) and monitor your favorite Pinterest pages, or scroll through the “New Arrivals” link at Zara every few weeks. These will keep you up to date on the acceptable and the adorable!  Then go try them on and make sure they’re not torture. I also carry a mini first aid kit for shoe-mergencies for those pairs that let the pain set in only after you’re past the point of returning them. Love these blister bandaids (they  make them for toes too), moleskin is a must, and sometimes these little guys do the trick for toes.
In the alternative, invest in a timeless pair, like these or these.  And don’t forget about boots!  They can be comfy when you can throw on a cozy pair of socks and hide them under a chic, flat boot like this, this or this (my fav, duh).  Finally, if you can get away with sneakers, pick some cute pairs like this, this or this and revel in their comfort.
Cute (but comfortable) flats wishlist: these, these, these, these, these, these, these and these.
Our office is business casual to casual because it is an agency. I am not a creative, but I need to look put together every day. How do I look business appropriate for my position without looking overly formal?
JC
TTL says:
See my above distaste for what business casual can make people do.  In order to avoid all this, I’d stock my closet with a few essentials that can be on constant rotation.  I’ve created a capsule that does just that.  Check it out here. And I’ve posted some biz cazh styling ideas on my Pinterest Q&A page!
Can I still wear my oversized watch? What’s the current watch trend?
TA
TTL says:
I finally parted with mine after not wearing it for a good three years.  However, if you want to continue to get the most out of your investment, I’m sure it’s fine to still wear.  I definitely wouldn’t stack other jewelry around it “arm party” style like I was doing hard in 2011. Think minimalist; these days, less is more.
If you’d prefer to update, I’m liking something very grown up and classic, especially for the everyday/office.  Maybe like this.  Or an investment piece I’ve got my eye on (rather double heart googly eyes on), like this.
I am trying to clean out my closet. What types of pieces would you suggest hanging on to versus donating/tossing out?
RB
TTL says:
If I haven’t worn it in year (meaning it’s full season has gone by without you picking it up), I would strongly consider moving on (see selling tip above).  Unless it has some real sentimental value or truly brings you joy, there are not too many other reasons to hang on to something.
Now what about the things you are still actually wearing, but probably shouldn’t be?  That’s a case by case basis and, you’re in luck!  I can help you with that!  I offer closet clean out and in-home styling services.  If you’re interested, send me an email!
What can I wear over a formal dress to a wedding in the fall / colder months other than your standard shawl?
TA
TTL says:
I like a longer duster coat.  Options here and here.  Or, depending on the dress, you could use a fancy blazer or tuxedo jacket.
 
What are good work pieces that could easily transition into going out at night/happy hours?
RB
TTL says:
I love the old tear-off-the-blazer-and-let-the-cami-out trick.  I’ve been opting for more comfortable, less stuffy blazers like this and this.  Either of which I would honestly wear out whether I was coming from the office or not.  Camis are going to be everywhere this fall (layered over anything) and so are bodysuits, so pick up a couple that easily go from day to night, like this, this or this.  It’s hard to un-office a pencil skirt, so if you’re planning on heading out after 5, I’d opt for a cute ankle pant or culottes that day.
But really, tbh, if you’re of a certain age, you should be able to throw a jacket over almost anything you would wear out and make it work for the office.  If your going-out wardrobe consists of too-short mini skirts and bodycon club wear, you might want to reconsider that entirely.
What is one thing I NEED for fall 2016?
TA
TTL says:
This is a tough one because there are so many big trends coming up, but I would say a fun ankle boot. This pair is multiple trends in one (sock boot, block heel, green, velvet).  I also like these, these, these and these.
All of the jeans I see recently are flared. Are skinny jeans really on their way out?
KR
TTL says:

Not at all.  If you have a great pair, they are classics and not going anywhere.  Here are some of my favorite timeless looks: these, thesethese and a few more here, here and here. It will be a long time (if ever) that we would look at someone wearing a good pair of skinnies on the street and wonder, “What are they thinking?!”  That said, see my advice on the next denim question, below.

Flared jeans are coming back. I obviously kept mine from 2005. Would those be dated or can I recycle them?
RB
TTL says:
I get that things that are in will eventually be out, and what was once out will be in again.  However, most of the time, it will be with a fresh take or new styling.  So, while I would say, yes, flares are back in, I would give a cautious, “yes” for whether you can reuse the same jeans you went to Econ 101 in.   If you’re willing to consider new ways of styling them and you don’t expect to wear them the exact way you did over a decade ago, then maybe you can make them work.
I think a good rule of thumb when you’re going to bring something out of retirement is to balance with something new that’s either super on trend or looks expensive.  That way you don’t risk looking like you woke up out of a time machine, or, worse, have just been wearing them ever since and don’t even realize that they went out. It tells people you know what’s up and these are not a mistake.
For this particular item, I’d play up the 70s style and pair with a tight tucked in tee and maybe a vintage Gucci belt.  Or a silky cami and a long duster jacket.  I’d most certainly wear heels, and I’d prefer a block heel, a platform or mules – again, anything to avoid wearing them exactly how you would have worn them in college. However, given that these were around 10 years ago, there’s a strong possibility that they were hemmed for flats.  In that case, I’d opt for a fancier strappy sandal, like this or this.   If all else fails, crop them even shorter.  The kick-flare jean is everything right now.  Check out more styling ideas on my Pinterest Q&A page!
Note, however, that I think the biggest issue with the old jeans is going to be the rise.  While flares are back, really only high rise, or a good mid-rise, will work.  Those low-slung numbers that we thought were a good idea over a decade ago are gonna earn a hard, “NO” from me now.
How do I walk in high heels so it doesn’t look like a chore? Is it just a matter of wearing them more consistently? Some people look so awkward in them, and I don’t want to look like a klutz…
JC
TTL says:
Slowly and carefully.  I’m not what you would call a graceful person, so this usually is kind of a chore for me.  The most important part of getting this right is making sure your shoes fit.  If they don’t, there’s not a whole lot you can do to avoid looking like you’re either wincing in pain, stumbling across the finish line of an ultra-marathon or about to topple over like a toddler in mom’s stilettos.  If this means giving up the sky-high, super skinny heel, then that might be the ticket.  Opt for a more grounded block heel, a cute lower option or even a kitten heel.  You could also try these little tools for achieving the perfect fit.
I also find that one little trick works to help me look more like a lady…I try to put one foot in front of the other (just horizontally, not heel-to-toe, if that makes sense), as if I’m walking on one straight, painted line.  In other words, your stride length can be normal, but try not to have each foot land more than a few inches from your center line.  Obviously, we can’t be running errands all over the city keeping this form, but use it when it counts.  Good luck!