I love Suz's suggestion of a style icon of someone you admire...I'd add in starting a Pinterest board of what you think the next phase job should look like...
I highly recommend finding a few trendy pieces when the time comes... I replaced an entire wardrobe after losing weight and it wasn't until I stopped thrifting and added more trendy pieces that I felt the balance between classics and trendy...

Love this thread, as I'm frequently trying to up my game when I want to look polished. I'm enjoying the tips, and will have to try some myself.

Astrid, I had another thought. You really, really like a full skirt with pleats or fullness, and you like dresses that have skirts with volume. I'm thinking of your plaid skirts and dress and your "wedding" dress. This is a really cute look on you, but it is young. You may be doing this because you have fit issues due to a tiny waist; the solution is alterations. Fit your hips and have the waist adjusted.

In terms of makeup, there are a number of "BB" products out there that are multi purpose of treatment, sunscreen and a bit of tint. This may be a nice option for you--sunscreen is always great. Tinted lip balm is another way to ease into make up without looking painted or suddenly unlike your usual self.

I went through/am still going through this transition myself, so I understand how difficult it can be. It doesn't help that I'm petite and look younger than I am, either.

I support what others have said in terms of adding blazers and real shoes, not just sneakers and ballet flats, and paying attention to fit. I don't necessarily feel that you need to get rid of all of your tees and cardigans though. Maybe upping the game with interesting necklines (as opposed to basic crew or v-necks) or details would work. I know you're usually pretty minimal with your accessories, but a statement necklace, metallic belts, etc. can go a long way to upping the ante. And be careful not to get rid of your entire student/casual wardrobe - you'll still have lounge days and casual weekend days where a tee is what you'll want to wear.

Haven't read the other posts.

You are quite the natural beauty, and that is always going to be you, no matter how "grown up" you decide or want to be. We could strap you into a dry clean only skirt suit with 4-inch killer pumps and an inch thick mask of Sephora makeup, and you would still manage to look like a beautiful woodlyn nymph. I say roll with what you've been gifted, and I think you know that already-- because your preferences are also for natural fabrics and fashions too.

So my gut reaction is to suggest that instead of overly focusing on the haircut, find a great colorist and add just a hint of color. Just a hint. Don't go overboard. Natural, but maybe just an oomph of red or gold or something. I don't know what. Go with semi-permanent color so if you hate it, it'll wash out quickly. Or highlights, and if you hate them, you can get a semi-permanent over them.

Experiment with hair color first, before fine-tuning the clothing colors. Wear white to your color appointment.

I'd also recommend color on your eyebrows. I would love to see what a difference darker / shaped eyebrows would make. That may be all you need. I don't use eyebrow pencil myself, but I get my brows shaped and when they've just been done, I need a lot less makeup overall.

As for clothing colors, yes, you do look fabulous in the lighter summer shades.

Woodlyn Nymph - that would be the color "season" I'd categorize you into. But it's very broad. It could be autumn, spring, summer woods. So I say - start with hair color first, to choose which season you want to play "grown up" in for awhile.

Astrid, recognizing good fit is a huge step and good for you for having achieved that! It would definitely be helpful to find a reliable tailor. If, for instance, you need to have blazers/jackets altered, it would be helpful to send them to a good tailor!

Good luck, Astrid, and keep us all posted!

Have not read through the other thoughts yet, but here are mine:
Color - this was really a big thing for me that helped me hone my style. I'm a soft summer (maybe soft summer deep, because I think i can wear darker shades well) and when i started to focus on wearing flattering colors and purchasing only items that are really flattering I think it helped elevate my outfits. Maybe pick one or two colors (maybe one neutral, maybe light grey?, and one color that you like) and focus on searching for a couple key items you really enjoy in those shades to start?

As far as specific items, I found that leaning more towards jackets - especially in more upscale fabrications like tweed or leather - also increased my style quotient. I don't know if you wear leather (maybe faux is more practical anyway). I find I rarely need to clean these (once every couple years, max).

Hair - I can't really help you here, sorry, my own hair at the moment is growing out because it's all I can do to just keep my grey roots colored and keep it in a clean ponytail. (-:

If you can afford the maintenance, maybe try a new shade?

ETA: two more thoughts...make sure your shoes, handbag and clothing are in good repair. Do let go of anything that's badly scuffed or worn. Also, keeping things as simple as possible but in decent (natural when possible) fabrications tends to help make things stretch more because you can dress them up or down more easily. But one or two statement items also helps, too.

ETA2: OK, I've read through all the thoughts. Wow, a consensus on getting a blazer, eh? Maybe you can start by wearing something you already own more often and see how that feels. (-; I agree with Dianna's thought on overall silhouette and that pencils skirts read more dressy and polished than full skirts. Also the comment (kiki?) about needing to get things altered to fit your waist - I have to do that very often. I will say, as far as silhouette for trousers, slim ankle trousers may work better with flats. If you choose to do a trouser leg then you should at least go for a pointed-toe flat and watch that the length is long enough (tricky with a flat shoe).

Thanks Rachylou! I've given up on ballet flats alltogether because they don't work on my feet. I don't think I can give up on jeans, although I'm alright with not sporting a hoodie...

Thanks Tracey. I'll definitely keep my eyes open for some inspiration! And yes, a Pinterest board is a good idea.

Amiable, I'm glad this was helpful.

Thanks Kiki! My plaid dress and blackwatch skirt are cut straight, so it's true that I don't have any pencil skirts. I'm not a big fan of them because they hinder me too much walking, I have a long stride and do a lot of swift walking. So straight cut skirts are alright, but I probably won't be happy with a pencil skirt that really narrows at the knee. Love the tinted lip balm idea! I'll have to search for one of those multi purpose creams, but that might not be very easy because I have very sensitive skin (with a penchant for bouts of neurodermatitis), which leaves a lot less and often expensive options. (I'm using essential oils at the moment.)

Thanks Dee! Not getting rid of anything wearable for now, my wardrobe is that small. I won't need to practice one in one out for a while yet. I do wear my sneakers a lot right now, mostly because I'm lacking alternatives. I don't wear ballet flats anymore.

Thanks Shiny! You know, that outfit you're describing sounds like my worst nightmare... Generally I'm very hesitant when it comes to hair color. The few times I tried color in the past (whole head or just strands) it never did anything for me. Actually that's one reason to suspect I might not be a Light Summer or spring after all, because those usually go blonde successfully. Cool blonde is harder to get right artificially, so I might be cool after all. Also anything darker or warmer looks off too. Red is a bad idea... Same for my brows - actually that's one area where I did a bit of experimenting with make-up, because my brows rather dissapear left on their own. I haven't yet found a color looked naturally on me. I do tweeze my brows though, I have for the last ten years or so. But very carefully, I don't want to make it worse. I do tweeze the stragglers under the brows and on my nose bridge (my brows are naturally a bit closer together).

Thanks MsKatieKat! I will keep you all up to date.

Thanks Jenava! You do color in a fantastic way. Love it. I'd like to get to a similar place myself. I do wear leather, but a real leather jacket is quite expensive so it has to be an investment piece. We'll see. Good point about letting go of pieces that are getting too worn - I guess I do wear some of them longer then I should because I have to keep an eye on the budget. As for my blazers, I only have two cropped black ones. They only work with skirts and black isn't very flattering on me. Both were bought for specific occasions (one for a funeral). So I don't have a blazer I could wear with my everyday outfits at the moment.

Astrid you've had some fab advice already, which I can't really add much to and I agree that you don't need much make-up at all. You mentioned your eyebrows though and that was one thing I was going to mention as I swear by Clinique Superfine liner for brows and they actually do a soft blonde colour which may be nice and subtle for you. I love that the pencil twists up with no need for sharpening and you can do really fine feathery strokes with it : http://www.clinique.co.uk/prod.....mpl?cm_mmc Hope this helps.

Thanks for the tip, Diane.

Soooo I have no background in business/business casual environments (and thank goodness if they require giving up full skirts & cardigans ), but if you just want a generally more grown up style, I thought of the blogger from Small Notebook and her discussion of 'comfortably dressy' in these posts: style guide, dressier small wardrobe, and shopping guide. She has a little section dedicated to her clothing posts, and as she's into voluntary simplicity, you might resonate with her approach.

I also wanted to add that I have a ton of silk or silk blend tops, both knit and woven, that I wash in my washing machine on the 'hand wash' cycle and dry flat/hanging (depending on if it's knit or woven) without any problems. Of the 30+ tops/dresses I've treated this way, one has changed from satin-like fabric to a washed silk feel; the rest have stayed the way they were when I got them (and one was satin-style and new when I got it). It's really not that fussy of a fabric! You do need to be careful if there's a lining though, as often the lining is made of something else, so if there's minimal shrinking of the silk, the lining can end up showing underneath. I think that's only happened to me with linen or wool items I was deliberately trying to shrink via the drier though; I don't think I've tried to shrink anything silk or had an issue. Also, one of my silk tanks reacted strangely to deodorant or my sweat & now has a discolored dark spot around the underarms. That's the first time that's happened to me out of all of my silk tops, but I suppose it is a risk. I think it has to do with the tank being slightly too big, and I was wearing it backwards for a higher neckline, so there was fabric bunched up right in the 'high sweat' zone. Anyway, silk/cotton blends are lovely!

Linen is a very strong/sturdy fabric that just gets softer as you wash it, so unless it has a lining that doesn't want to be washed, no worries there either.

I just wanted to come back and commiserate with you about how hard it is to walk in a skirt that isn't a poof.

If you still like the poof (and I love my poof) for your tiny waist, just try to pick some more adult fabrications and colours. I rarely wear my baby pink poof even though I really love it, but I'll try to find one with a thicker material and more substantial weight ... after July.

LOL Eva, I really don't think I have to give up full skirts and cardigans full stop. I do want to be more dressy, but I have no idea yet how dressy I really need to go later on and it could be more on the casual side anyway. Thanks for the links, I didn't know her blog. Definitely looks interesting! And thanks for the fabric and washing tips. I do fear though that I won't be finding that many great quality silk (mix) or linen (mix) fabrics out there - those fabrics are usually only used by brands above my budget and I don't have the opportunity to thrift like you do. I'm going to keep my eyes open though. There are always sales!

Thanks Lyn. I think I can get used to the idea of a few more straight cut skirts that are tailored to my waist, but I definitely don't want to give up full skirts completely! Good idea to keep the color and fabric more "grown-up" looking.