1. Get over the label.
This is one of the hardest things for women to do. They were a 6 before and now they are a 10. They were a 12 before and now they are an 18. It totally sucks, but here's the reality: you are dressing the body you have RIGHT NOW. Not the body you had before or want to have again. And while you might be planning to lose weight, work out, whatever, you can't go around naked or wearing your husband's sweats every day.
So let it go. Do it! Right now! You can cut out the tag, lie to your friends, pretend it's a different number or letter. But get over it, because otherwise, the rest of what I have to say will be meaningless.
2. Buy cute shoes.
Also, if you don't have them, get ballet flats. Yes, ALL OF YOU. No, they don't have as much support as Asics. And they don't have as much sex appeal as stilettos. But trust me, you will be happy you have shoes to wear that aren't meant for the gym, pool, or a stripper pole.
And slip on shoes ARE just as easy to slip on as flip flops. And you can run after a kid just as easily in flats as in flip flops, Uggs, or Crocs. So just put the plastic/furry shoes down and back away slowly.
3. Get naked.
You heard me. This isn't a warm and fuzzy Learn To Love Myself thing, people. This is a You Have To Acknowledge Your Body Shape In Order To Dress It thing.
I'm not a fan of categorizing people's shapes like fruits (apple, pear, etc.) or geometric shapes (inverted triangle, rectangle, blah blah). I do subscribe to Kendall Farr's idea of Types A, B, and C. I highly recommend her book, The Pocket Stylist, btw.
Loosely speaking, Type A is bigger on the bottom than the top, Type B is roughly the same size top and bottom with a defined waist, and Type C is somewhat straight up and down. No matter what size you are, the theory goes, you maintain the same body type. (Women who are bigger on top than on bottom, I'm afraid you don't have a type in this theory. But you could follow guidelines for Type B, most likely.)
For women who carry your weight in your midsection, you too have to look at what your proportions are. You will almost certainly fit into one of the three main types.
The keys for all of us? Highlighting the smallest part of your waist (yes, it really works) and working WITH your body shape, rather than trying to pretend it's something it is not (yep, it also really works). These two things are your reality check. If you find yourself in something you don't find flattering, ask yourself whether these two things are true.
I am not going to go into a lot of detail right now about what works and doesn't work for each body type. For one thing, a lot of useful books have been written on the subject. Hit me up for a recommendation if you'd like. For another thing, the real work isn't in knowing what to wear, it's in knowing what NOT to wear. So that is what I'm going to focus on, with some suggestions on what to replace those forbidden pieces with.
4. Don't hide in black.
Newsflash: not everyone looks good in black. Are there colors that you wear and get complimented every time? Colors that make your eyes pop? Colors that seem to work for you every time you put them on? THOSE are the colors to reach for.
A note on favorite colors: if you like a color that doesn't look great on you, you have two options. Wear it away from your face or wear by your face and change your make up to make it work. Not a great make up artist, I tend to keep colors that don't flatter me (like orange) to my footwear and accessories.
Color theory is another broad topic about which much is written. I am a Donna Fuji fan, so invest in her books- or a consultation with her if you are in the Bay Area- if you want to learn more.
Suffice it to say that these things hold true almost all of the time:
a. You are probably wearing at least one color that does not suit you.
b. You are probably avoiding at least one color that does suit you.
Without a professional's opinion, I recommend trying on a bunch of colors and having an honest friend tell you what they think. You will probably get a sense pretty quickly of what works and what doesn't.
One (very) broad generalization: most redheads don't look great in black.
My point? Don't hide in black because you think it's slimming. If it doesn't fit well and the color doesn't suit you, it's not doing anything for you.
5. Run, do not walk, away.
If you like this stuff, fine, but if you want to wear what is most flattering when you feel somewhat (or a lot) heavier than you'd like, just get over them.
(Disclaimer: almost anything I list here will work for some people, some of the time. So read it knowing that I get it- sometimes you post-pregnant/struggling with body issues/want to hide figure flaws people can make this stuff work. Some of the time.)
Get over: skinny jeans. They are not your friend.
Replace with: dark rinse, straight leg, boot cut, or slightly flared jeans. And just because you haven't been jeans shopping since 1981 does not mean all flared or boot cut jeans are "bell bottoms." Get over it and TRY THEM ON. If you find a pair you love, buy at least two pairs, preferably in two different washes (no super light or acid wash, please!). If you wear heels and flats, get one pair hemmed for flats and have one long enough for heels. If you wear only flats, have them both hemmed.
A note on hemming: not much looks sloppier than pants dragging on the ground. Sloppy does not equal slim and feeling great. So hem your damn jeans.
Get over: giant t-shirts. They are hideous and make you look bigger, not smaller.
Replace with: fitted tops. If looking slimmer is your goal, shirts that skim your figure are best. Even better? Shirts with some structure, like darting at the waist or seams under the bust.
Get over: kitsch.
Replace with: on-trend (yeah I hate that phrase, too) patterns
You know who you are. But you aren't fooling anyone with your Tinkerbell sweatshirt and Power Puff Girls bag. Winnie the Pooh, people?! Are you freaking kidding me? Buy a book or a freaking figurine. Don't wear this stuff any more.
Distraction can be a useful tool, but we are going to do it with adult patterns and shapes, not juvenile crap that just demeans us. Right? Right.
6. Shop somewhere else.
So, this is one more thing to get the hell over: your preconceived notions about what looks good on you and what doesn't.
I have experienced this myself and when helping others shop. Here's the rule you MUST shop by, until you have a great handle on what works and what doesn't: Try Everything On. Like a top with a tiny floral print and aren't sure you can pull it off? Try it on. Love that dress on the hanger? Try it on. You are not required to buy anything you don't love, but you are required to try on lots of different things for a while.
The best way out of the rut is to shop in places you don't normally go into. I found two amazing dresses in a shop I'd previously avoided because I thought it was too expensive. Not only were they in my price range, they are awesome dresses I couldn't find elsewhere.
Always go to Ann Taylor? Go to Anthropologie. And make yourself try on at least 4 things. Hate them? Fine, but at least you tried. Always hit The Gap? Go to Nordstrom. Online shopper? Try a bricks and mortar store or two.
Shopping somewhere else is the best way out of any sort of shopping rut you are in.
I could go on, but for now I leave you with this: Dressing yourself is not just a set of skills you acquire, it is an attitude. You dress for yourself first, and others second. And dressing for yourself means wearing what makes you feel confident/amazing/insert happy option here.