Soothe my fears about transitioning from scruffy to well heeled

[NervyMcNervous]

So I used to take care over my appearance, used to have a fairly neat well put together look - we are going back some years here mind - that meant I always looked presentable. I knew what suited me and I felt quite happy with my clothes.

Fast forward 10 years and post DC I have somehow got to the stage where if I put on proper makeup I feel like a clown (though others don't notice, they may say "you look nice today, what did you do?" for eg). I wear converse, jeans, T shirts, technical jackets. If I have to go somewhere that involves wearing a frock, I either HATE the whole experience and feel like Aunt Sally from Worzel Gummidge, or I find some excuse not to go.

I have got some money to spend on a new wardrobe (clothes not the furniture obv.) and have been buying a few things, but I am looking at the new cashmere cardigan and new lovely brown leather shoulder bag and thinking I will never wear those, they are not practical, they will get ruined etc.

The whole thing is making me feel very stressed and it is meant to be a nice thing.

A lot of it comes from having put on weight, at least 2 dress sizes. I have been thinking "no point getting anything nice until I lose weight" for about 8 years. I have decided that no, actually, I can still look nice - I don't need to look like a drab mouse just because I'm a bit bigger than I used to be.

I am actually losing weight but don't mind getting new stuff now anyway.

How would you go about getting new clothes in these circumstances? Little at a time or draw up a list and get everything in one go?

I am in a very similar situation.I have morphed from a size 10 Maxmara wearing thing to a size 14 flabby body.I am also currently losing weight [and going to the gym lots].The gym has helped me to feel better and more confident about myself and my body.Though i still find it difficult to find flattering clothes.I do buy expensive coats and cashmere[albeit reduced at TK Maxx]because i hate wearing cheap clothes.However i also buy basics from Matalan and M&S,at the size i am now.These can be replaced without too much expenditure in the future.Brora and Me and Em do really nice dresses that can be belted when you lose a little weight.Do enjoy the cashmere and the leather bag as these will make you feel good about yourself.After all cashmere can be easily machine washed on delicate wash.Feeling good about yourself will give you a more positive outlook on life[and everyone needs to feel a little spoilt] as family life can be quite draining.

If you can afford it, how about getting house of colour style and colours day? Then at least you will know what suits you.

What about booking a personal shopper somewhere like Debenhams or John Lewis and getting them to do the running for you and try a few different looks? It will give you ideas as well for when you go shopping yourself - sometimes its just hard to know where to start.

When I am stuck sometimes I just get a complete new outfit including accessories. It means you have one top to toe great look and generally most of the stuff will work with other things you have.

On the question of things getting ruined well they might!!! But what's the point of them just sitting in the wardrobe? I do this too - buy something lovely and then not wear it but it's totally pointless - wear the lovely stuff now, life's too short to put off enjoying the good things.

Yes, life's too short not to smell the roses. It's why I have decided to treat myself now - I was forever seeing a lovely thing and dreaming of the day when I could wear it. Meanwhile, I was wearing horrible things that made me feel miserable.

I have had my colours done and although I don't actually like some of my best colours (salmon anyone?) it does help knowing that brown and teal and grey and red are good but purple and black and dark green are bad. Helps you focus on the choices.

The idea of the personal shopper is a good one. I avoid shops mostly and shop online, so I will often choose a shape that is really unflattering and disappointing.