Teaching our daughters to dress well: eight tips

Nobody taught me how to dress myself.

I was a typical teen. I followed along, buying everything my friends said was cool or trendy, never asking myself whether it looked great or was good value.

Occasionally I’d read an article about “backbone wardrobes” or “classic fashion”. But classic fashion didn’t suit me. I look uncomfortable in a suit, awkward in most jewelry, and downright ridiculous in anything too girly!

So I ignored fashion, thinking it wasn’t for me, and all the while dressing poorly, with clothes that didn’t fit well, didn’t wash well, didn’t look good.

Does any of this sound familiar?

These days I dress well, with fewer clothes. Far fewer clothes. I’m experimenting with the ten item wardrobe. Although I’m not down to ten items, I’m on my way.

I’ve figured out what suits me, I buy quality clothing, I’m not afraid to spend money on a single good item, and my wardrobe is small.

If I could go back in time, I’d wish I’d been taught to dress well. I think my mother was as awkward with fashion as I was – as lost in it all, although she always seemed incredibly beautiful to me.

I think she didn’t help me learn, because she’d never learned herself. Had she known, we could both have saved ourselves thousands – and much pain.

So here’s how to dress our daughters well:

1. Learn what colours suit youColour Me Beautiful is a great tool – but don’t be afraid to break the rules. For example, I’m a “Spring”, but I can wear black, as long as I keep it away from my face.

2. Find at least one style of dress that looks great on you, and is cross-seasonal. For me, that’s “swing dresses”: 50s-style dresses that are fitted in the bodice and flare from the hip. I buy dresses in fabrics that can be worn all year round, and dresses warmly with tights and leggings, or cool in summer with just a pair of sandals.

50s style swing dresses can be very flattering, especially for larger women, and those with larger bone structures.
50s style swing dresses can be very flattering, especially for larger women, and those with larger bone structures.

3. Don’t be afraid to buy quality. I’ve bought dresses I’ve worn hundreds of times that are great quality – and t-shirts that were cheap and looked awful or shrunk after just one wash. Cheap often isn’t a bargain – not if you have to replace it over and over, and it doesn’t look great in the first place.

4. Buy quality shoes that are cross-seasonal. My leather ankle boots are worn all-year-round. I look after them, and they look awesome every time I wear them.

5. We commonly dress teenagers in trendy, cheap, ugly clothing. I think teens deserve great clothing that is good quality, even if that means they get less of it. We can either teach our teens to dress well and understand quality and style, or we can encourage them to buy cheap rubbish. I’d prefer to teach my teens style. I think they deserve it.

6. Fit is everything. If it doesn’t fit properly, it won’t ever look good. Check out this Basic Guide to Proper Fit and see what a difference correct fit makes!

7. Make fashion work for you. Fashion comes and goes, but most of it won’t work for your daughter, unless she’s one of those rare people who looks great in practically everything. Teach her to be discriminating. For example, when the “pastels and lace” trend was in a few years ago, it looked terrific on my best friend. On me? Ugh. Sometimes taking a photo in the change room when trying items on can really help clarify things.

8. Buy investment pieces – even as a teenager. An investment piece is any item that lasts more than a season, and is replaced because it wears out, rather than loses quality (shape or stretch, pilling etc.) or fashion. Good investment pieces for teens to begin with might include:

  • Hiking boots
  • Great quality leather ballet flats
  • A medium width leather belt
  • A thick winter jacket or puffer jacket
  • A denim jacket
  • Great quality jeans that fit well
  • A cross-seasonal dress for day wear that fits well. Styles to try might include fit-and-flare, rockabilly, A-line and sheath
  • A cross-seasonal, fully lined evening dress in a dark colour and simple style that fits well.

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