Learning How To Dress Up

“I’m completely sick of dressing down and jeans and such. I want to start wearing skirts and dresses and dress pants. I’d like to stick to black and red and white if possible. Any suggestions on where to start with completely re-vamping my wardrobe?”

Yes! This can be broken down pretty simply into a few steps:

Take stock of what you have
Go through your wardrobe & separate it into a few piles: Keep, Maybe & No. The first & last categories are fairly self-explanatory, but the middle pile (“Maybe”) needs a bit more thought. Try things on, see how they fit you & consider what else they go with. Get rid of the things you never want to wear again. You may find that the only way you stop wearing plain t-shirts is to donate them to charity.

Think about what you’d like to wear
You’ve said black, red & white are very appealing to you. I must suggest that you look at Miss Nubby Twiglet’s wardrobe photographs. She is the queen of all things red, white & black, & she wears a lot of those colours, but you will notice that she doesn’t stick solely to those options. She also occasionally delves into blue, green & gray. It is possible to make strong colour statements without limiting yourself, so maybe that is something to keep in mind.

Nubby TwigletNubby Twiglet. Fabulous.

Further to the above, think about specific items you can imagine wearing
If you’re trying to stay away from jeans, maybe wearing skirts & dresses will be a major part of your new direction. Work out where you’ll draw the line — would you wear a miniskirt or can you only imagine yourself in something long? Would you like to incorporate vintage into your wardrobe or are you happier in new things? Think about this a lot & put whatever you come up with on paper.

Go shopping for core pieces
Always dress to flatter your body shape & colouring! Look closely at how the clothing makes your body look. If you look lumpy, short or rotund, don’t buy it. You might want to take someone shopping with you — someone with good taste & who has the ability to tell you “no”. I always find that going shopping with my mother is an enlightening experience, she picks things off the rack that I would never have even considered — & they often look fantastic.

When I say core pieces, here these might include a coat, a good pair of trousers (since you said you wanted to wear dress pants more often), some skirts & dresses. Depending on whether you want to stick to black/white/red or branch out a little bit further, I would suggest going for a black coat. You could even go for a coat with a little bit of a pattern or something, but a red coat might be too much first thing in the morning & if you ever want to wear green, your red coat will make you look like a Christmas tree. You see what I mean?

In terms of dresses, I would go for a few different styles but hopefully dresses that can be worn in multiple ways — with a t-shirt underneath, with a sweater on top, over pants or bare-legged, etc.

I love accessory shopping. Go crazy for these things since they enable you to wear the same outfit but look completely different simply by wearing good accessories. Buy hats, scarves, stockings, leggings, legwarmers, socks, hair accessories, necklaces, jewellery, headscarves, bags & shoes. (Glorious shoes!)

A note
Using a small colour palette can be tricky sometimes. It is quite rare to find a whole lot of things in the same shade of red, for example, so if you want to wear more than one red piece at a time it might be a bit of a trial.

Bonne chance ma petite!