How To Dress Yourself Part 2: Buy Good Clothes

Here's how you can tell if you have enough clothes. If your favorite pair of pants is in the laundry, how long does it take you to find a pair of pants, appropriate for the activity that you're planning to do, that you can wear, pair with a comfortable, appropriate, and attractive top, and know that you'd look good enough to feel highly confident if you ran into an ex and his or her most fashionable new flame?  It shouldn't take you very long. In fact, you should feel like you could choose one or two outfits that will make you feel good about yourself, for anything you are going to do.

So you have to go shopping, more often than you'd like to. Shopping, too, is harder than it seems.

The first thing to remember about going shopping is that it is not a sort of mundane, running-errands-so-it-doesn't-matter-what-I-look-like activity. It is an activity that you are undertaking because you realize that it is worth money to have clothes that make you feel like you look terrific, that fit right and that make you look like the kind of person you are. It is an activity that will require you to look at yourself in the mirror again and again in things that may or may not flatter you. You will be trying to picture your best self, and to decide whether the clothes you are trying on get you closer or further away from that. So you need to dress well to go shopping.  You need to put on the clothes that make you look like that best self -- poised, or professional, or fun, or hip, or artsy, and as attractive as you can. Dress like you're going on a date or an interview. Dress like you're trying to make a good impression, because you are. You're going to be looking at yourself way more than you're accustomed to and you want to feel good about what you see.

You also need to go to stores that have the kind of clothes you want to buy. If you're not sure, look at the other shoppers in the store. Do you like the way they are dressed? Do they look like the kind of person you'd like people to recognize you as? If not, are you sure you are in the right store?

The right kind of store has a couple of characteristics. It has fashionable clothes, in a variety of sizes. It is well lit. It is in a price range that you can afford, although you may not be happy about it. Stores that do not count: TJ Maxx and used-clothing stores. I used to shop almost exclusively at those places. A friend asked me why, and I explained that I liked the “treasure hunting” aspect of being in those kind of stores – finding the diamond amidst the piles of bad clothes. It was kind of an adventure. And I felt like I wasn’t being ripped off – the discount on the tag made me feel smart, like a savvy customer, rather than a sucker.

But the flip side of both of those attributes was making me feel bad about myself, which I didn’t realize. The “treasure hunting” aspect of stores like that meant that every time I went to the dressing room I had to ascertain whether something that I’d picked out was fashionable or actually stupid-looking. It made it harder to feel good about my decisions. And every time I would try something on and realize, oops, nope, this item is not fashionable after all, I felt worse about my own ability to choose. I can’t do this; I have bad taste; I don’t know how to dress myself; I’m a fashion mistake waiting to happen. And the discounted price just reinforced a mindset that I don’t deserve new clothes, or clothes that look nice, that I’m not allowed to spend money to make sure I look cute, that doing so is wasteful and bad.

Good stores limit the time you waste trying to decide if something is tasteful or not, or if it is attractive or stylish or not, or if it is reasonably well-made. That, I am realizing now, is worth money. Instead you can focus on whether it is appropriate for you: does it fit? (If not, you can try it in a different size.) Does it flatter you? Is the color good? Is it practical? Does it make you feel good about yourself? Will you smile when you see yourself in the mirror? Is it something you need? Will it work with the best things you have in your closet already?

It is helpful to have a fashionable and articulate friend with you, who will help you decide. This makes you more confident in your own decisions, and keeps you from blundering into the usual traps – shirts too big, in my case, or choosing clothes that are stodgier than my personality. And it helps you realize the features that work and don’t. Your pants need to be a little bit longer. Those kind of pockets don’t work with your hips. I’m seeing a lot of these slip tops, what do you suppose the right way to wear them is? You’ll think, I could never wear something like that, but you might try it on anyway, with your friend’s encouragement. And maybe it’ll turn out that you can, or maybe you can’t wear that one but you might wear something slightly less daring, but more interesting than what you would have imagined before you tried it.

The hard part is that you’ll need to keep doing this. You’ll need to buy clothes again, sooner than you think. You’ve got to get in the habit of paying attention to how your clothes feel and look, and what’s in style, and how you wear the things you have, and what is getting old and worn out. You’ll need to get in the habit of putting aside time and money to maintain your appearance. That’s hard.

And this is the hardest part, for me anyway. You buy the clothes that look good. You don’t waffle about it, you just do it. Even if they’re not on sale. As you get better at doing this, and as your closet starts to fill with clothes you like, you can get more discerning about price and value, and you can limit yourself to the sale racks. But you can’t do that at first, when you’re trying to dress the way you like. You need to actually spend money on yourself.

Comments

[CM]

Any tips for finding clothes that fit right? Part of the reason I avoid shopping is that it can take me hours to find one thing that fits.

[Yeoman]

Good clothes, that is appropriate clothes are like a tax on your income in practicing law. That is they are a hidden cost of doing business.

They are necessary, however. People will judge a lawyer on whether he looks like a lawyer. I find that if people catch me when I'm doing farm work they tend to be shocked, or even worried. I don't look right to them.

As a total aside, we live in the age of really bad dressing. That comment no doubt shows my age.

[ms]

I hate shopping with a passion. (Ex. I'm perpetually in-between two pants sizes, and I'm too old for "young" clothes but too young for "middle age" clothes.)

However, I love, love, LOVE the feel of good-looking clothes that fit right, have great fabric, convey the image of myself that I like to carry around in my head. The days I wear such clothes, I feel transformed--more confident, more attractive, more capable, more the ideal me.

I will also put in a plug for a good perfume/cologne as an essential part of one's wardrobe.

But what about accessories--the sartorial wild card? (Ex. is this scarf Parisian-chic or PTA-wannabe?)

[ML]

Rapid River (in Freeport) is having a 70% off sale May 20, 21, & 22.

[ilona]

So what are your own favorite sorts of stores?

btw- I love the Leon Bakst picture, one of my favorites.

[mythago]

As a total aside, we live in the age of really bad dressing. That comment no doubt shows my age.

Yeah, you must be pretty young. :)

I put in an anti-plug for perfume for people who have not been expertly instructed in its proper use.

[Diane]

I see the perfume anti-plug, and raise you a "please, please don't!" As it turns out, if a person can get through the week of withdrawl (read, extra-stinkiness) after kicking their perfume/cologne habit, said person will generally smell really quite nice.

What is the general consensus on women in suits, in the professional arena? Are we selling ourselves short by dressing "like men," or are we availing ourselves of the ages-old tailoring tradition? Additionally, lace (not spilling forth, so much as hinting at flair) with a well-fitted suit: yea or nay?

[Online Clothing Browser]

simply uying new clothes doesnot makes you look good. You also hsould have nie personlity to loook better

[Bartjan]

Thank you very much for this post! Insightful. I'm going to the store now - spending some money :-)

(Don't worry, I planned on going shopping before I read this - I wanted some tips on how to shop well)