THE BLOG

Put Your Fashion Anxiety to Rest

11/09/2009 05:12 am ET | Updated May 25, 2011

Fashion can be tricky. All the rules and faux pas, changing of trends, exceptions and scenarios...even the ultra-stylish must stop and think from time to time. There are so many questions and concerns that people deal with on a daily basis -- so I thought I'd take just a handful of them and put any doubts or anxiety you might have to rest.

I'm cleaning out my closet. How do I know when to get rid of clothes?
This is a very interesting question and the answer was put best by my best friend. "You just know," he said, "it's like love."

"But what if you make a mistake?" I pleaded desperately.

"Exactly," he said.

What he meant is that when cleaning out your closet, as in love, mistakes happen. You just have to acknowledge it and move on. If you want an actual technique I once read about a woman who turned all of the hangers in her closet the wrong way (so the open part of the hook faced out) -- every time she wore an item she turned it the right way. When 2 years passed, she got rid of any items on hangers that were still facing the wrong direction.

Can I wear white after Labor Day?
Are you living in a J.Crew catalog circa 1994? Yes, of course you can. That rule was created by some asshole who probably wore white in December, trudged through some dirty snow, stained his/her pants, and thought "Dammit! There should be a fashion law against this!" White is great. Wear it with health, as my mom would say.

When I wear my flats without socks they hurt my feet and frankly they start to smell a little bit. Can I wear them with those little socks, even if they stick out a little bit?
No you cannot. Either suck it up and endure the pain and stinkiness, or buy some different shoes.

I like to get my nails done -- when they start to chip, how chipped is too chipped?
Ah, this question is extremely circumstantial. Luckily for me, I live in a world of ambiguity, where totally polished is nice and pretty, but chipped off is punky and sassy. I love it when I first get it and I continue to love it 2 weeks after. If you do anything corporate or "professional" (meaning you serve people, they serve you, you go to meetings, you meet new people and represent your company, etc), you gotta take that polish off essentially at the first sign of chippage. Do this: extend your arm straight out in front of you. If you can't see chipping from that far away you're fine. If you can, others will too and you will look like you're not on top of things. For professionals this is a bad thing. If you're anything else -- an artist/bohemian, an athlete, a teenager...you know, whatever else there is...you can basically let it ride until it chips all the way off. Enjoy.

It looks good when I match my hat to my shirt to my sneakers, right?
No it does not. Oh wait, maybe if you...no, it does not.

Is it always wrong to pop my collar? Can I ever get away with it?
This is very simple. Are you a frat boy, varsity sports player or douchebag? Are said collars on polo shirts, button down shirts or letterman jackets? If the answer is yes to any of these then no, you may not pop. Conversely, if you're a model, artist, jazz musician, punk rocker or older than 45...and if said collars are on leather jackets, denim jackets, or anything uber-stylish and high fashion, then yes you may pop. You might look a little douchier for doing it, but as long as you have the awareness of this possibility I think you'll be ok.

I love sandals and flip flops! What do I do now that winter is approaching? How can I get away with wearing them?
You know what? Sandals and flip flops are summer shoes. You can't get away with wearing them in the winter because sandals/flip flops worn with socks is the worse possible thing you could do to your feet. Boots/sneakers/loafers/moccasins/other closed-toed things were invented for a reason. For the love of all things fashionable please tuck those things away until next summer.

That's what I have for now. I know, I'm a wealth of knowledge. Let me know if I can answer any of your burning questions...I live for it. Until then, happy shopping -- and good luck to you.