March Madness: Adjusting My Appearance

I know it’s five days into March and I’m just starting to write about my March monthly challenge. But honestly, I’m a little embarrassed about this one. But the idea for this month’s challenge came from a lot of different random experiences:

-Frequently getting mistaken by clients for the analyst instead of the manager because of how young I look and the immature way I dress

-Always having trouble figuring out what to wear to go out at night in NYC (pretty much the only time I really worry about my appearance) and constantly feeling like I have nothing to wear (despite the fact that my two dressers and two closets are all overflowing)

-Getting shocked reactions from my girlfriends when they discovered that I have never in my life been to one of the famous NYC department stores (nor do I even know where they are located, aside from Macy’s in Herald Square)

But when my friends in Puerto Rico ended up doing my hair/makeup for me and Ashley loaned me a dress to wear, I realized that I probably ought to do something about it.

Look how pretty I look! (Why don’t I look like this more often?)

I feel a little silly about the shallowness of it all, but it’s evident that I need to spend at least a little time focusing on my appearance. And so – that’s what I’ll be doing for the month of March.

I’m honestly kind of nervous about the month. I don’t want to spend a lot of money (and since I don’t tend to buy designer stuff, my expectations of “a lot of money” are probably much lower than those of my friends). I also don’t want to significantly increase how long it takes me to get ready for the day/night. But I do want to clean out my closet, keeping only the stuff that makes me look great (instead of the clothes that are just something to cover my body). I also definitely need to get some accessories, instead of defaulting to pearls and my oh-so-chic Nike Fuelband. And I clearly need to learn how to do my hair and makeup (quickly!) to look my best. Perhaps even a drastic haircut is in order? We shall see.

The adventure began last Thursday night (still technically February), when I hit up some department stores in Dallas to look for a formal gown. I started with some places that were new to me but where I was reasonably comfortable (Saks Off Fifth, Nordstrom Rack, Dillard’s) – but then migrated to some stores that honestly made me feel totally out of my element and like everyone in the store was judging me (Neiman Marcus). I didn’t find a gown that I liked, but I was able to make do with a dress I’ve had for years. It may not have been quite as chic as the designer dresses my friends got from Rent the Runway, but I still thought I looked pretty good, and I was very comfortable. Hooray for stretchy material!

Note that the lighting is kind of weird in that pic; I did not use any self-tanner nor was I orange like an Oompa Loompa.

That’s right, Saturday night found me at another place I never thought I’d be – the New York Junior League Winter Ball. I was honestly terrified in the cab on the way there, particularly because I had chosen to do my hair and makeup myself (hooray for this Youtube video of an easy updo!). But what if my hair looked like a rat’s nest and my face looked like a clown and I was the only one there not in a famous designer? Of course, none of that mattered in the least, and I had an amazing time dancing the night away with my friends. But I was still proud I pulled it off – first test, complete! (The next test will be when I go to Savor the Symphony in a few weeks with Blake and see if I can improve upon my all-dolled-up skills.)

I also put together what I think is a pretty cute outfit for work this morning. It’s nothing fancy, but it’s a bit more effort than my usual jeans-and-a-polo at my very casual client. And, it all came out of my existing closet – so it didn’t cost a cent!

No, I am not going to turn into one of those annoying bloggers who snaps a daily outfit pic… just today.

I was surprised that it wasn’t that hard for me to look a little bit better. It just took thinking about what I had and trying on a few things at home before packing them (instead of just grabbing the same old boring things and shoving them into my suitcase like I normally do). I think if I just spend a little more time up front figuring out what works and what doesn’t (and perhaps a lot of time clearing my closet of those “doesn’t work” things), I can look a bit more pulled together all the time, instead of kind of a tomboy-ish mess. Whether I like it or not, the way I look is the first impression I give off, so it really ought to be a good one.

So – and I can’t believe I am writing this call to action – any hair/makeup/fashion advice? Any tips on how to clean out your closet when you’re a totally sentimental pack rat like me? And, should I finally go to the New York department stores that scare me so, or should I take my friend Lacey’s advice and avoid them because it’s “adorable” and “quaint” (like a Luddite) that I live in NYC and have never been?

This challenge pressured/sponsored by Blake, Ashley, and Theodora – and to be very clear, I love them dearly for it.

Comments

  1. Beth @RxBethOnTheRun says:

    OMG my friend, I don’t know where to start with my response! A) I purged ALL of my closets right before the new year and would be HAPPY to come over and help! I’m GREAT at closet cleaning; complete with hilarious stories of when I cleaned my grandmother’s closet and plenty of wine to make the night even more fun! B) I just bought a bunch of new clothes and can share my secrets at said closet cleaning event ;) Email me and let’s plan to clean and shop! and C) I need all new makeup, so let’s go together :)

  2. Love this idea for a challenge, it is time I went through my wardrobe as well, it is overflowing yet feel like I am in your situation a lot with “nothing to wear!”

    I work at Avon and would be happy to pick up a couple things for you to try out if you let me know what products you use/are interested in and what colors you like. I have pretty much transitioned to all our products now and am actually planning a post on my blog about my own skincare/beauty routine soon!

    NYC department stores – I totally get where you are coming from; I always had fun browsing Bloomindales but can’t picture myself at any of the even higher end ones like Bergdorf Goodman etc!

  3. I have this issue too. I’m allowed to wear whatever to work, so it makes it worse. Every year, I think that I’m going to do like cute casual and I end up doing sloppy casual.

  4. When can Ash and I come over for a closet cleanout??? Also, although I love love love the fancy department stores, it’s mostly just for browsing, or picking up 1-2 items and getting most other stuff at lower-priced stores.

  5. I am very excited for this challenge! I look forward to helping you find some new and exciting pieces!

  6. The first thing I do when I’m doing a closet clean out is get rid of anything I haven’t worn in a year. For picking up new pieces, I would invest in one or two basic pieces, like a nice pencil skirt (if that’s your style) and a blazer that can be worked into a variety of outfits. Most things I end up buying at lower priced stores, or trying to take advantage of sales.

  7. Wow, thank you EVERYONE for all the awesome comments! I was so nervous to post this because I was afraid it made me sound shallow, so it’s nice to know that others are on the same page :) I think I may have to throw a closet cleaning event with all my friends soon…

    Karen, really looking forward to your post and thank you for the offer! I don’t know what I use yet but I think your post will help :)

  8. I would recommend actually trying on everything in your closet to see if it fits and make sure it’s actually in good condition. With what’s left, evaluate which styles and cuts you really like and make you feel the best version of yourself. As silly as it sounds, the show What Not To Wear was instructive in how to go about putting together a closet of clothes I love.
    As a former consultant who spent 50 weeks a year on the road, I found the best strategy was a wardrobe of slacks all in the same cut, button-down shirts, cashmere sweaters (warmth without the bulk), and a couple pencil skirts so that it was super easy to pack and not think too much about how to put together an outfit. Except for the sweaters, everything was machine washable for maximum convenience on the road.
    Lucky you going to Nordstrom’s in Dallas! The service and selection make it my favorite place to shop and I hate that there’s not a single one in NYC.
    Good luck!

  9. I read once that it helps to give all your clothes a grade – things that look great and make you feel great are an A, look pretty good are a B, and so on, down to clothes that are drab and icky and they’re an F. If you think of your closet as having a GPA, you don’t want to drag your closet’s GPA down with clothes that don’t look good and make you feel good. I find this to be more useful when it comes to resisting sales on clothes that are probably a B/C, but I had some success with purging on this system, too.

  10. Umbereen, my usual has generally been kind of a uniform as well; where it gets trickier is that my current client (which I’ve been at for a year now!) is extremely casual. Not business casual, but casual-casual! Most people love it, but I have always had trouble putting together outfits that are casual enough and yet still put together. I agree that finding things that I really like and fit well will go a long way!

    Gwynne, I am DEFINITELY going to use that letter grade idea – that’s a great one :)

  11. I went through something very similar in the fall when I changed jobs. I had to find a more ‘distinguished look’ that didn’t make me look like I was 16, and obviously not allowed to wear my running clothes to work. I don’t think you need to go to designer stores, you just need to find a happy medium of what works for you, but step outside the comfort zone a little.

    • Laura, I think you’ve hit the nail on the head – just a matter of actually THINKING about it instead of doing my default.

  12. A good friend of mine and I were discussing the difficulty in finding clothes (professional, weekend, casual,…) that actually fit our bodies and look good. It seems like the normal size is becoming exceedingly un-normal (at least from a male perspective, I have no idea of females).

    We both acknowledged the trend of fewer and fewer tailors and not really knowing what sizes we actually wear, other than a “medium” or “small”.

    I definitely believe in the adage “dress for success” and I am slowly putting goals in front of me to help me, such as: finding what sizes actually fit me well so it is easier to shop, finding a tailor/seamstress to perhaps enliven some stuff I have, figure out what ‘style’ makes me feel like a million bucks, only bring in clothes (to my closet) that contribute to my positive self-image.

    Probably not really helpful to your particular challenge, but it is something that I think a lot of younger, err, new adults out there struggle.

    • Danny, I actually really appreciate that comment in part because I was curious what you would think of this challenge :) You always leave really great insights and, as I continue to mention, I feel a little silly focusing on my appearance. Perhaps a post is in order about the importance of dressing for success, with research to back it up? Interesting to see that men have similar issues.

  13. Anonymous says:

    I don’t think you need to go to those department stores. I think the key to looking pulled together is making sure your clothes are clean and not stained, fit well, and are not stretched out, faded, or otherwise worn. Also, think classics instead of anything trendy.

    If your client’s office is very casual, then just stick with skinny jeans, flats, and a nice top. I would stay away from polo shirts. Personally, I think polo shirts are for summer weekends in the suburbs. They don’t really belong in a city and especially not at work (although they are fine for men).

    With regard to hair, very long straight hair is not considered very professional. It tends to look juvenile. It looks more professional to keep hair no longer than a few inches below your shoulders. Also no cleavage! Showing a lot of cleavage is not very sophisticated and frankly showing a lot of cleavage is what 18 year old college students do – not professional women.

    Makeup is a must unless you are working out or lying around your apartment. You should definitely be wearing it to work.

    Also, it is always better to be over dressed than under dressed.

    Take a look at some well known professional women online and see how they dress, like Sheryl Sandberg. Use them as your wardrobe role models.

    Good luck!

    • Thanks for all the advice! I think I do okay when I get to wear business casual or business formal, but definitely struggle to put together work-appropriate casual outfits. I am SO with you on cleavage not being okay at work!

      As for hair, that’s one of my biggest issues that I’m still pondering. I love having long hair in general, but you are SO right that it doesn’t look professional in the workplace…

  14. Hi- I have the same problem of trying to make my college student wardrobe more twenty-something professional woman. I use the website jseverydayfashion.com because she blogs about how to dress nice without breaking the bank! Just a thought!

  15. I get nervous whenever I go into Bloomingdale’s…I can stay for about ten minutes before I realized I don’t belong and I leave.

    I would need all the help I could get on this challenge…wearing scrubs to work doesn’t exactly lead to the most professional wardrobe, and the only nice pants I have are a pair of black pants that I bought to interview for nursing school in back in 2006. For the most part, I think I look like I’m 12 when I wear dressier clothes (which is never). I usually wish my look was more put together, but I don’t ever have a reason to dress up, so jeans it is. I like the jeans/blazer look, but I have no idea what I’m doing…a stylist or something!

    And make-up…don’t get me started. I’ve worn the same look since I was 14 when my mom took my sister and me to the make-up counter at Clinique. Girl fail.

    • Susan, you and I are twins. I can’t stay in places like Sephora for more than five minutes without wanting to run crying. Too many options and I don’t know what to do with any of them!

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