fashion advice I learned the hard way

Fashion Advice I Learned the Hard Way

Sometimes people ask me for fashion advice. No, really, they do: I promise I’m not making this up. 

The problem with that, of course, is that most of the time I don’t really have much in the way of fashion advice to offer: I’m very far from being a fashion expert, and some days that’s more apparent than others. In fact, almost everything I’ve learned about style has been learned the hard way (Actually, almost everything I’ve learned AT ALL has been learned the hard way…), so today I present some fashion advice that you probably already know, but which I found out through trial and error. And sometimes even MORE error…

the best fashion advice I've been given

First, dress for the weather. 

I spent a lot of years of my young life wandering around in the freezing cold without a coat: not because I was a fashion blogger, you understand (this was way before fashion blogging was even invented, young ‘uns), but because I was stupid. I thought coats weren’t cool enough for my fly self, so every morning on the way to school, I’d wait until I was just out of sight of the house, then I’d stuff my sensible coat into my schoolbag, and continue on my way. I thought I was awesome. I was freezing. Oh, and I didn’t look any more stylish either: I just looked like someone who didn’t know how to dress herself – which was pretty much the opposite effect from the one I was going for, really.

Fashion advice taken: before you consider anything else about your outfit, think about the weather. Because you will not look stylish with blue skin and icicles dangling from your nose – trust me on this.

Next, dress for the occasion

I know a lot of people advocate wearing whatever you want, whenever you want, because you’re just so special and unique that everyone will be blown away by your daring refusal to bow to sartorial convention. Or something like that, anyway. The thing is, though, while in my head I’d love to be the kind of Carrie Bradshaw-type person who wears a tulle skirt to the supermarket and doesn’t give a damn what anyone thinks about it, in my heart I’m just not that girl. Oh, I’ve been that girl: or I’ve tried to be, at least. (Disclaimer: I have never worn a tulle skirt to the supermarket. Or not that I can recall, anyway…) But I’ve learned the hard way that I’m just as uncomfortable when I’m overdressed as I am when I’m over-dressed, and I feel most confident when I’m wearing something that’s at least somewhat appropriate to the occasion. Who knew?

Fashion advice taken:  You probably wouldn’t wear wellies and jeans to someone’s wedding, so it’s probably not a great idea to go hiking in a wedding dress, either. Because no matter how amazing you look in that dress, people won’t see YOU at all: they’ll just focus on the inappropriate dress, won’t they? As we all know, you should wear the clothes: the clothes shouldn’t wear you, so dress for the occasion as well as for the weather. That doesn’t have to mean dressing the same as everyone else, by the way: it just means knowing how far you can push the boundaries before things start to get awkward.

Wear shoes you can walk in

People frequently ask me how on EARTH I can walk in my shoes, and when they do, I always think, ‘Come on: surely you don’t think I’m stupid enough to wear shoes I can’t walk in?” Then I remember the time I tried to climb a mountain in clogs. (You’re trying to work out what’s more shocking here, aren’t you: the fact that I climbed a mountain, or the fact that I wore clogs?) (In my defence, I was 16 at the time, and clogs were, like, SUPER fashionable, OMG.) (Also, we got a cable car to the top of the mountain, so it was just the very last bit that I tried to… I’ll stop talking now.) Or the many, many times I’ve decided stilettos would be the perfect choice of footwear for… actually, I’m not even going to list all of the times I’ve thought stilettos would be appropriate when they SO OBVIOUSLY WEREN’T APPROPRIATE, GOD.

Why did I do these things? Because I would rather have died than wear flat shoes, obviously: why else would I do it?  Of course, what you all know, and I only learned after a lot of blisters, is that nothing bad will happen if you wear flats every once in a while. Well, if you’re me they WILL make your legs look stumpy, and that IS pretty bad, to be honest, but then again, so is limping over sand in a pair of 5″ stilettos, isn’t it? I think so.

Fashion advice taken: wearing shoes you can’t walk in (Or SHOULDN’T walk in, under the circumstances: I actually CAN walk in all my shoes, and I posted some tips on how to walk in high heels here, if you’re interested…) doesn’t make you look stylish. No one looks stylish when they’re staggering along in unsuitable shoes, so while you’ll still have to prise my stilettos off my cold, dead feet, these days I also wear flats if I think they’re going to be more appropriate…

Get everything tailored

I have a bit of an awkward shape. I’m slightly too tall to be “petite”, and slightly too short to be “regular”, plus I have a long torso and a completely flat chest: and trust me when I tell you that not many people are making clothes with THAT mix in mind. The fact is, though, we ALL have slightly awkward shapes in some way or other, don’t we? I don’t think I know a single person who can walk into a store and know that the clothes will fit her perfectly, right off the rack – and yet still we all persist in buying clothes off the rack, and expecting them to fit perfectly.

Fashion advice taken: I remember reading once that celebrities have EVERYTHING tailored: even thinks like t-shirts and tank tops are adjusted until they fit like they were made for them. Now, I’m not going to take it quite THAT far, but I do have quite a lot of items altered to fit, and it makes a big difference.

Trust your instincts

You know all of those times you’ve stood in front of the mirror, twisting and turning as you try to work out whether that dress you’re trying on looks good, bad or simply indifferent? Don’t buy that dress. Seriously, just put it back RIGHT NOW. I’m watching you. Oh yes I am…

Now that I’ve got you all freaked out, I can honestly tell you that not ONE TIME has an item I haven’t been sure about turned out to be a great purchase. Not once. The sad fact is that if something doesn’t feel right the first time you try it, it probably won’t feel right the second, third, or any subsequent times either: and if it doesn’t FEEL right, then it doesn’t matter how good it REALLY looks – the fact that you don’t feel comfortable in it will stop you enjoying it and feeling your best in it.

Fashion advice taken: These days I have a simple rule whereby if I try something on and don’t instantly think, “OMG, I LOVE this: I MUST have it!”, I don’t buy it. I mean, I make an exception for basics like t-shirts, or whatever – I’m probably not ever going to be blown away by them, but if I need them, I’ll buy them anyway. With things like dresses, though, I really have to love to them: and if I don’t feel comfortable, I don’t buy, simple as that.

When you find something you really love, buy multiples

Finally, and on the subject of things I really love, I can’t even count the times I’ve looked at them, fallen head-over-heels for them… and then totally missed out on them, because I decided to wait for the sale, or wait for next Tuesday, or do something else equally incomprehensible, that’s led to me missing on that perfect item. And there’s really nothing worse, is there? Other than all those things that are undeniably much worse, obviously?

Fashion advice taken: If you love it, buy it. Then buy a spare one, for when it wears out, or you spill red wine on it, like you always do.  Actually, this is a piece of advice you sometimes CAN’T take: I mean, I love my newest pair of boots, but I can’t exactly go out and buy multiple pairs of £160 boots, can I? (Answer: NO.) I also don’t advocate buying things you really can’t afford, or getting into debt over dresses, so be sensible, kids. But if you CAN afford it, and you REALLY can’t live without it… don’t. Or you’ll end up like me: a bitter and twisted old woman, endlessly searching eBay for a pair of shoes from 2009, that you probably wouldn’t wear now, even if you found them. Er, don’t do that.

Got some fashion advice you learned the hard way? Please share…

  • The Other Emma


    Hear, hear to all of the above but particularly the altering clothes to fit. I’m your long torso, flat chested twin here and the difference a little but of tailoring can make to something is amazing.

    All do not wear trends just because they are trendy. Wear them because they suit you otherwise you (yet again) just look like you got dressed in someone else’s clothes.

    December 9, 2015
  • I am yet to wear shoes that are comfortable *hysterical laughter*. Honestly though, how do you find the Vivienne Westwood Melissa shoes? I have some of the pairs that you have and although they are the correct size, they cut into the sides of my foot something awful…NOT THAT IT STOPS ME WEARING THEM.

    December 9, 2015
  • I agree with everything you said. Sadly I can’t wear flats, I really can’t. They are uncomfortable and I get so many blisters. I got 2 pairs and I had to through them away after trying hard to walk in them. I’m the crazy lady on high heels in the forest because her husband wanted to show her a beautiful spot he saw while walking the dog (it was far from home and I didn’t had any trainers with me). This year I managed to find a pair of low heels that I liked and I wear those as much as I can just to avoid the “oh dear, she is so inappropriate” looks.

    December 9, 2015
  • FM


    Wear clothes in the size that fits you, not in the size you *want* to fit you. No-one sees the lables, but everyone sees the too-tight clothes fitting you badly.!

    December 9, 2015
  • I am in massive agreement on the tailoring thing! I’ve literally just got a dress that when I put it on nearly made me cry as it made me look so ridiculous – the shoulders on it were sitting an inch above my own. I’m not exaggerating that. I don’t even know how they were holding up like that, but they were. A £20 trip to the tailor later and it looks amazing! I’m so ridiculously happy with it now. I’ve gone to the tailors about 50 times this year (or, it feels like it) and it’s been worth it every single time. Oh, and while we’re talking about things you’ve bought multiples of – just got those Lindy Bop trousers and it’s LOVE. Even if they are full-length on me…

    December 9, 2015
      • Susana


        Did you blog about some Lindy Bop trousers? I’d love to see what you’re talking about.

        December 22, 2015
          • Susana


            Thank you! I’m on the hunt for new pants (or trousers as you would say) since I realized I don’t have any that are appropriate for the office. They can’t be leggings (eww…leggings as pants?) and I can only wear jeans on Fridays. I’ve had too many Marilyn Monroe moments in my full skirts so I’m now on the hunt for wiggle dresses/skirts and pants. ?

            December 23, 2015
  • Oh, I agree with so much of this but ESPECIALLY dressing for weather and trusting your instincts. Without a coat, you’ll definitely look cool, if you catch my drift, but you definitely won’t look smart! This is also why I don’t understand people who wear rolled up/ankle pants in the winter with no socks. You know what I mean? Cozy sweater, scarf, snug skinny jeans and… exposed ankles. Why?

    Trusting your instincts though, that should be obvious. Why do we think that we can make it work? Getting dressed shouldn’t be hard or take a lot of thought! Thankfully, most of my blunders have at least been thrift store items, so not too much money down the drain.

    December 9, 2015
  • I just can’t trust my “I love it” feelings. A lot of pieces I’ve felt that way about in the store have just been worn a few times because I realize that they just don’t look that great on me. (Skater dresses pretty much every time that happends, so now I don’t buy them anymore.)
    Instead there I have some things that I bought as base pieces for my wardrobe and then end up loving. Sometimes I don’t even get how good they look on me until a year after I bought them and then it’s way late to buy another one.

    The best advice I can give someone else is to not play by the rules. Go your own way and dress in what makes you feel good about yourself./love Ida

    December 9, 2015
  • Fabulous advice, Amber! I’ve never actually gotten any of my clothes tailored… probably because I’ve got a pretty standard (read average) body shape. I’d love to have clothes made for me though… perhaps one day when I’m super rich 😉
    Suzy x

    December 9, 2015
  • Nicole


    I’ve gotten a lot better lately at only buying things that work with the rest of my clothes. I love patterned pants but I just don’t have enough plain/neutral tops to wear with them. When I was younger I was pretty bad about buying cute patterned skirts which I would then discover only went with like one or two of my shirts.

    December 9, 2015
    • My answer to that is get more plain and neutral coloured tops 😛 I’m currently obsessed with patterned trousers and found that I actually have a use for all of those plain boring tops lurking at the back of my wardrobe that I never bothered with before

      December 10, 2015
  • lalie


    Wear all your clothes, don’t keep anything “for best”.
    (you could even wear your Christmas jumper in August if you really insist! No, I mean that after keeping all your advice in mind first, obviously)

    Your size might change drastically, and nothing will fit anymore. You might suddenly completely change your hair colour, and need a new look. You might relocate and be faced with a different climate. You might see that beautiful outfit you were saving on your boss (or your ex or that girl from Big Brother in Essex). Fashion changes, either everyone is now wearing your coat/ handbag (and you don’t want to look like a fashion victim) or they are looking just dated.
    My advice would be to wear everything whilst you can and whilst you want to, weather and circumstances permitting!

    December 9, 2015
    • Exactly. I keep telling people to wear all of those gorgeous things they have but nobody listens. They’d rather wear jeans and t-shirt all of the time because they think a full midi skirt is too much to go out in and then complain they never get an opportunity to wear all of this finery. Blah

      December 10, 2015
  • Annabel


    I feel you on the awkwardly shaped part. I’m also slighly too tall for “petite” and slightly too short for “regular”. I’m naturally very skinny, flat chested, with small hips and very long legs. I’d basically look like a little China doll if it weren’t because I have a GIGANTIC back. Ten years of swimming really do get you, right? It’s so big I can’t wear strapless or halter tops without looking like a gorilla in a dress. On the plus side, full skirts really balance out my shape, and I love me some full skirts…
    Also, for someone that claims to know nothing of fashion rules, you know quite a lot. You’d be surprised at the amount of people that don’t know these

    December 10, 2015
  • I have finally learned, after many many mistakes, to trust my instincts when buying clothes. As much as I try and make myself like the things I first questioned in the dressing room, I never do. I can relate to several of these fashion mishaps of yours… Live and learn, or try to anyway. ?

    December 10, 2015
  • Trudy


    I only learned last winter how great it is getting your clothes tailored to fit. I bought an expensive coat ($400 – not sure what that is in £) that I absolutely loved. The shop got it in specially for me, so I had to make a guess on the size. It seemed to fit OK in the shop before I took it home, but when I got it home I realised it was about 2 sizes too big, even allowing for layers underneath. Whenever I sat down all the extra material would rise up around my ears. The shop refused to exchange it (I haven’t gone back there since, I was so mad at them). I wasn’t too hopeful but I took it to a tailor to see what they could do, rather than waste all that money. They worked pure magic with it, and I wore it solidly all through winter, definitely getting my money’s worth out of it! Since then I have taken all my dresses in to be altered as well. My hips are a size larger than my bust, so its very rare to find something off the shelf that perfectly fits me.

    December 10, 2015
  • I learnt the “buy multiples” rule the hard way too. I have a pair of wedge booties which are the most comfortable shoes I have ever worn. I managed to wear them during a whole day sightseeing in London, and my feet didn’t hurt more than they would have done in trainers. Pluse they are nice, the heels makes them a little dressier than trainers and I love that. But they are three years old now and starting to get really ruined, so I’m afraid I’ll soon have to give them up. And I can’t find them on ebay. If only I’d bought another pair…

    December 10, 2015
  • On my computer, I keep track of my wardrobe with 3 lists: The 1st list (on my computer) is what I own that’s in decent shape. The 2nd list (also on my computer) is alphabetized by event (such as a long-standing New Year’s Eve Party) or friend, then under that I enter what I wore. The 3rd list is just a small write-on pocket calendar that I fill in every day with the outfit and the location/event. These lists help me get more mileage out of my wardrobe and not bore my students (I’m a substitute teacher) or my out-of-town friends whom I see infrequently.

    December 25, 2015