Matching V. Going & the Perils of the Foodservice Industry

Dear Leith,

I remember when you would help people before in their time of need and noticed that you'd want to do it again. Well perfect timing because I need your help. Yesterday I started my (disgusting) job at Dunkin Donuts. I'm can't think of any think that will make my khaki pant, red-orange with textured ridges on the side polo uniform look better, do you have any tricks up your sleeve?

Sincerely,

Megan

The first thing I thought of when I read your e-mail was the episode of Ugly Betty where it's revealed that Amanda's been working at T.G.I. Friday's to make rent money. Yes, I watch Ugly Betty. I know it's embarrassing but I love Amanda's clothes. So, let her be some inspiration to you. Get creative! Amanda may have to wear a horrible uniform but she spices it up with fun accessories (sequined suspenders).
I'm assuming that they aren't giving you the khakis so opt for a straight leg, and make sure that they fit you fantastically. Seriously, get them tailored if necessary. Too baggy or too tight and no matter what else you wear you'll look absolutely terrible. Besides, you will always be able to use a great pant.
The hideous orange shirt? Do your best to make it snazzy. Try rolling up the sleeves (but not all the way, one or two rolls maximum). You can definitely jazz it up with some great jewelry (are you allowed to wear necklaces and rings? if so GO FOR IT, if not then wear the best earrings you've ever seen). Remember, hair and make-up got a long long way.
Last of all, wear awesome shoes. If you can stand it some killer high heels (in black though, that bone color is awful) would be awesome with some skinny khakis and that polo. If you can't though wedges are just as fab. Also, if you do go with an open toe make sure you've had a pedicure, no one wants gross feet while they're buying some donuts.

Leith-

First, just wanted to tell you that I thoroughly enjoy reading your site. moving on...

When it comes to choosing my outfits,I tend to accessorize very sparingly. The accessories I choose are so matchy-matchy, it's almost embarrassing. I'm completely lost. I get the concept, I guess, but I have trouble when it comes to executing it. I hate myself for this, but if I wear a black shirt my hands automatically reach for the black purse...I really don't want to become the matching pant-suit type.

any suggestions?
-Olivia

Things don't have to match, they have to go! Just like Stacy and Clinton taught us. Now, I love matching my purse with my shoes (I like to think of it as bookends to a wonderful outfit). But sometimes you have to break free of the monochromatic uniform! Experiment with your wardrobe. Try going with something that you aren't comfortable with, even if it's just in the privacy of your own home at first. Feel free to keep it simple, but also not matching. The Sartorialist is always great inspiration, especially for dealing with colors. It may sound strange but the menswear he features is some of the most inspiring stuff for me. Speaking of inspiring menswear, Gossip Girl's Chuck Bass is a perfect example of using color in fun and interesting ways. If only there were more modern dandies out there.
P.S. I will always love monochromatic outfits, but the way to make them really work is pair interesting textures and designs.