Styling questions answered

The hurdles we all face and how to jump them

Hi, I’m Leigh. I’m a stylist and my interest and passion for styling is focused on how we feel in what we wear. Dressing is a form of self expression and I work to empower people to align their sense of self with their style and gain autonomy to dress with ease, clarity and confidence.

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We all come up against similar hurdles when getting dressed.

“A wardrobe of clothes and nothing to wear / Feeling uninspired / Not knowing what suits me / Struggling to find the right jeans / Clothes don’t feel like they reflect who I am / Not having the right shoes / Not feeling like ‘myself"‘ etc.

I asked my paid subscribers to fire any styling or wardrobe questions they have my way and I’m sharing the answers here, for you all.

Whatever you struggle with when it comes to getting dressed, let me assure you - you are not alone.

Don’t let hurdles stop you from dressing how you want to.

If I miss anything you want the answer to - ask away and I’ll cover more in another post soon.

See this as your free styling session! I hope it’s helpful.

HURDLE: I struggle to know what to wear each morning. I try on 100s of things, and often nothing feels ‘right’.

FIX: Intuitive dressing.

If you haven’t learnt this concept from me yet, then I think this is going to be really helpful.

When cooking a meal, you start with the ingredients.

When getting dressed, don’t go straight to the clothes (aka meal in this analogy), check out what ingredient’s you need first.

• How am I feeling today? How do I want to feel? (Bold, confident, quiet, soft, flirty, cozy etc etc.)

• What fabrics do I want to wear? (Something warm, light cotton, sexy silk.)

• What colours do I want to wear? (Black to feel confident, red to feel vibrant.)

• What am I doing today? What do I need to feel supported? (Walking, commuting, resting, working etc.)

By checking in with yourself first and identifying the ingredients you need to support yourself each day, you set yourself up for success before you’ve even gotten to the wardrobe.

You are different each day and you’ll want and need something different each day too.

For example, you have a job interview - you want to feel confident, capable, comfortable and together. Choose an outfit that embodies that for you.

Or maybe you’re recovering from a big week or you’re going through something difficult - your answer to Q1 might be that you want to feel calm, soft and safe. Then choose cozy fabrics that create those feelings.

Fabrics and colours allow you feel and express in a certain way, a chance to bring your personality into a look. A way to express yourself anew each time you get dressed - so feel into how that looks for you.

And finally the practical element is there to support you. If you are walking a lot, choose your most comfy shoes and build your outfit from there.

Do all this BEFORE you go to your wardrobe, and watch how this information not only helps guild you to what to wear, but also allows you to feel like you. I promise it will help.

Here’s a image of the questions. Save this on your phone in your favourites album or on your notes for easy access each more.

I speak on this in more detail below..

HURDLE: Wardrobe full of clothes and nothing to wear.

FIX: 10 minute styling sessions without the pressure.

A lot of us don’t need more clothes, we need more time to play with the clothes we already have.

It’s really hard to put a cohesive outfit together in the morning if you’re time poor and feeling uninspired.

What you’re going to do is prepare ahead of time.

Now I don’t mean pull out all of your outfits for the week on a Sunday night (unless this speak to you and works for you -David Beckham said he does just this in his doco.) Personally, I like to follow my intuition when getting dressed each morning so pre-planning in this way isn’t for me. d

BUT, this isn’t about setting outfits in stone, it’s about carving out undisturbed time for yourself to have fun and experience with your clothes.

Set aside 10 - 15 minutes once or twice a month. (Longer if you can.)

Go to your wardrobe and pull out an item you’ve been wanting to wear but haven’t yet. Try it on and create an outfit (or two) with it.

What did you first envision you’d wear with this when you bought it? Try that on, and try something else.

The goal here is to have fun and explore. The pressure to find an outfit is off, so you’re more relaxed to experiment and see what feels good.

If you do find an outfit you like, take a picture of it and save it on your phone in an outfit specific album.

Next time you’re stumped for something to wear, you’ll have some pre-styled looks ready to go.

Snippet from a Style Guide I created for a client

HURDLE: Difficulty finding jeans

FIX: Know your measurements, know what you like and try on at home with the rest of your wardrobe

I won’t lie, this isn’t a quick fix. But there are some tips that can help make the search for the perfect jeans smoother.

1. What style of jeans are you after? Baggy, relaxed, fitted, cropped?

2. What rise suits your shape? What are your measurements?

3. Choose a pair based on your measurements, not just your waist size.

4. Try on with the rest of your wardrobe and the shoes you want to wear them with.

I wrote a full jeans breakdown on how to identify the right pair for you a few weeks back. Read below.

HURDLE: Shoes!!

FIX: Invest in pairs that you will actually wear

I don’t think a personal styling session goes by without someone expressing that they struggle to know what shoes to wear with a look. Or that they don’t have the right shoes in their wardrobe.

I believe the problem here is that shoes are often left to last when it comes to considering our wardrobe.

We focus on the outfit, the bag, the make up, the hair and shoes are a last minute thought.

And I think this is a mistake.

Considering the shoes first, or at least at the same time as the outfit is key to feeling like your outfit works.

Shoes are the practical element of the outfit - they take you where you need to go and you need to feel supported by your feet.

But they can also make or break an outfit.

I will do a full write up on shoes soon so stay tuned, but until then, I invite you to look at the shoes you have in your wardrobe. Ask yourself:

• Are they comfortable and do they support me?

• Do they go with the clothes I wear?

• Do I like them?

A surprising number of people don’t actually like their shoes - and this is a big part of your outfit not to like.

Do some research of shoes you like in stores &/or on other people and pin down 2 - 3 styles that would work with your outfits and in your daily life.

Brogues, ballet flats, sandals and boots are a good place to start, if that suits your personal style.

Invest in shoes that fit you and are well made, you won’t regret it.

And consider how a different shoe will change your outfit. Instead of going for the obvious - try something different.

A loafer with your track or lounge pants or a heel with your sporty shorts. By juxtaposing the outfit (aka teaming opposites together) it creates contrast and interest and might just make that everyday outfit extra special.

Image from Pinterest

Image from Pinterest

image from Pinterest

HURDLE: Feeling uninspired.

FIX: Take a break. Then follow your interests.

I’ve spoken about this a lot. (See articles below including my conversation with Courtney Adamo.)

But some new advice I want to add is something Tracy Anderson said in an interview for the Financial Time’s HTSI magazine..

“I stop trying to be inspired. Most people aren’t uninspired - they are over-filled. Inspiration returns when interference drops. I go towards what is alive.’

I love this so much!

Stop trying to find inspiration. Go outside, read, cook, swim, laugh - whatever it is you do for fun. Once there is space, the inspiration will seep back in.

And when it does you’ll have a clearer head to follow the steps I recommend here.

If you have a question to ask or issue you want help with, let me know, and I’ll do another one of these posts soon.

X Leigh

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This is a newsletter dedicated to style, thoughts, and self expression by stylist and consultant Leigh Williams. The best way to support is by forwarding this to a friend or becoming a paid subscriber for additional benefits such a 20% off a Wardrobe Styling Session.