What a wonderful, and methodical, way to take Angie's advice to heart! You have done so well. I agree with the other comments about your hair - that it is lovely as is, and that you can work towards a sharper angle in the future. I love how the red glasses bring out such great depth of color in your eyes - that is so beautiful! I'm very glad that boots ended up more comfortable. I think that it is really cool to be true to yourself when it comes to your foot wear! I agree with what someone else said about the grey top - a longer under-layer that is more contrasting, and perhaps has a collar, would be so great! And I see that I am in the minority, but I really love the handbag! I am SO not good at determining what is current or dated when it comes to handbags, but I have a dogged loyalty to my own preferences in that area. So in this case, you have hit upon something that is totally "me" and I can't get past that.

Amy, your hair looks great. Next time be sure that you take a photo of how you want it cut. I ask for a blunt cut with the longest part in front. Sometimes my stylist cuts layers in back. I don't mind as long as they blend together.
The glasses look wonderful. I was going to say that I'd like the sweatshirt bigger and more fluid, but looking again, I think it fits well, as do your jeans. I hope that the DocMartins loosen and get more comfortable. It sounds like most need to be broken in. Your bag looks more ladylike than tomboy, but could be anything that you want it to be. If you are looking for something different, maybe a backpack bag or a tote in a color close to that of your Docs?
You have worked hard on your style and it shows. Great job!

I love your haircut and both pairs of glasses, the red ones are particularly stunning. They really enhance your features.

I think the handbag is fine, I do like the fact it has brown and black in it which makes it easy to style. I could see a satchel style suiting a tomboy, or even a backpack. So that could be something to consider when you are ready to upgrade.

Amy - I look at your pics and see a beautiful woman - actually with some polish, as well as some edge. I am just amazed at how your style has evolved since you first joined YLF! Thank you for sharing your process with us! It's really been helpful - I've learned so much from you! I LOVE your hair at this length - and sure, it could be shorter in the back with a more defined line between the back and the sides - but I say just enjoy this cut until you can go into see your stylist again! Also, I love both pairs of glasses and am so envious of your beautiful skin and lips! You are a natural beauty. I want to see pics of your handbag wardrobe before giving my opinion on this particular handbag, OK?

I think the hair is great! I am constantly tweaking, refining and just changing up my own hair, so don't think of it as a final product - it's a constant project! I like the glasses. I guess my question is what are the specifics of the style direction in which you want to head? "Updated" doesn't really convey anything specific to me... or did you post about this elsewhere already?

I also think you're right that what I'm looking for is a tomboy take on
something that's also somewhat classic. Maybe the best of two worlds?

You know, that's just what I'm going for - just on the other end of the continuum I think. I settled on simple, grounded and feminine for my style descriptors and love them. I think I'm coming more from the feminine side, but needing that simple and down to earth vibe (kind of tomboy) to feel like the shoe fits. Definitely minimal, but not necessarily RATE and not edgy either. It's a look it's hard to find pictures for, I tried posting some down below. I think you might be just on the other end of this - mainly loving the tomboy and grounded looks but needing to add a dose of classic or feminine to it. Does that make sense? Like Una said, I'd love to hear more about the style direction you're going for.

Have fun, Amy! I love that you're taking steps towards your new look!
The others have already given great advice, so I am just chiming in to agree that your bag isn't dated to my eye, it's just reads more minimalist/classic to my eye rather than edgy.

Perhaps biker boots might be another option for footwear?

Astrid - you've described it perfectly. And you're correct - we're leaning toward different sides of the spectrum. I think we're both going to end up mostly classic, with mine more RATE, and less lady-like, and yours more lady-like and feminine than RATE or hard-edged.

As far as direction - that's hard for me to define - because I'm looking to be true to 'my' style and myself, without really knowing quite what that is. But I do know it has a tomboy element, and just a touch of hard edge (too much feels depressing or clowny to me - but just a bit feels right, at least at the moment). I'm do think I'm honing in on it - just not quickly

Regarding the purse - in addition to the backpack suggestions, what about a messenger-bag style, or do an image search for "man purse" - there are lots of great bags for men these days, and you might find one that's perfect for your wonderful tomboy style!

Can't get past how fab your hair & specs look. You are definitely going in the right direction!! I'm agreeing that the bag style might not be quite the one for you, but you are looking really good.

Your hair looks lovely. And the red specs are prettier than the black. Glad you are keeping those and not the black.

A bag update is a great idea. xo

I like the hair-- I understand what you wanted. It is possible that your hair won't play nice with it with the wave in the underlayer. I wear mine in a style somewhere between yours and Unas and have had to go more asymetrical and less angled because I have a cowlick that wants one side of the bob to flip out instead of under if it is cut angled-- if you are willing to heat style that can be overcome though. Adding a tiny bit of color in the form of a streak or highlight twice a year might help you feel a bit edgier and bring out your rich warm eyes (I have a similar eye color). I like the red glasses, several years ago I had a pair that color which were favorites, and the thicker top edge modernizes them. Going up one lens size (i find glasses styles come in small medium and large, plus EXTRA large) might make you feel more modern. Medium lenses are a really good balance between current and flattering and give me the best field of vision. I tend to splurge on a pair of frames and then wear them for 4-5 years, because I find they last longer than look more current for longer if I go for a high end edgy pair. Otherwise I have to replace my specs every 2-3 years which is actually more expensive because my lenses are actually as expensive as the frames often. I like to go to the most trendy boutique I can find, at least to try on styles.

I LOVE the docs and the bag. I have a pair of docs waiting to be decided on currently (Zappos is currently shipping me the smaller size to compare) but mine are nice and roomy-- although I often have the pinky toe issue because one of mine is further back on the foot than it should be because of an old injury.

In your style journey I would love to see you focus on fit for your classics and experiement with edge in acessories.

And ASTRID--- I'm really glad you posted. I love the inspiration pictures for you. I would love to see you in some reds and purples -- with your beautiful hair it would be goreous and adds the feminine touch to your jeans looks. For skirts I would consider adding menswear-esque prints to your tops.

Amy, I actually gasped when I saw these photos. This update is so interesting to me! And you look so very pretty here. You have a beautiful luminous skin.

First off, I love the hair and I agree that you can continue to tweak it to get the look you are after.

And I really like the glasses, especially the red ones. They frame your eyes beautifully.

What I see when I look at these photos is someone who is actually a bit polished as well as a bit edgy, a bit tomboy, and a bit classic.

Hmmm. Maybe you are an industrial urban prince? Or maybe industrial isn't the right word at all. And maybe urban isn't, so much, either. Maybe you are a Prairie Prince.

In all honesty, I think that a lot of black and hard-edge fights with your natural colouring and body type. At the same time, I understand that you are unhappy with an overly classic look, and an overly polished look feels precious and probably unsustainable, given your lifestyle.

I wonder if Marley could be an inspiration here. Black is not her buddy and she uses it quite sparingly. Yet she still maintains an edgy look. Hers is probably a bit TOO edgy for you (given where you live and your lifestyle). But the way she marries edge to a softer colour scheme and some feminine touches -- it might be something to look at?

I almost feel as if "rugged" might be a better descriptor than "industrial." Some of your pieces need to have a bit of solidity to them, and others need to be quite refined. A mix.

In the end, I sometimes think we "core modern classics" use the words "edge" or "twist" as shorthands to describe something that is awfully difficult to convey -- and then sometimes these words, in turn, take us in the wrong direction. Edge becomes too hard, too dark, too sombre. Twist becomes too quirky, too twee, too vintage/retro. What we want instead is something different. And what it is, we must discover...(as Virginia Woolf once said about her own fascination with clothes.)

Amy, I love the more modern bob! Did you lighten your hair as well? It totally suits you! The specs look great too! And yay for docs! I don't think those shoes would ever go out of style!

I'm glad that made sense to you. And I think you'll be just fine if you trust your instincts and take it slow. I think doing this process slowly definitely had some advantages - I've realised that I'm sometimes prone to really want things that I couldn't care less about a few weeks later. Not being able to buy them just because I wanted to saved me a lot of money for sure. The things I'm always coming back to over time, that is what I'm really looking for.

ETA

Thanks Elly. I will try to introduce more (right) colors in my wardrobe going forward. I'm definitely not one who would be happy going all neutral!

So cute and it all comes together in photo #6. Love your haircut and I also like the idea of a messenger-style bag, which I think would look great along with a few other suggestions that are flowing here, too. There were some really cute fringed bags in today's paper which added a modern element when I saw them.

Wow - love your hair and the specs Amy!!!

Amy, it's so interesting to see these pictures and to reflect on the transformation that is happening. You look fantastic!!!

I love the haircut, and I'm not surprised your reaction is to want more change there. (That happens to me a lot when I do something different with my hair, which is often. Sometimes a hair change is really a door opening ... so you are right to sit with it for a while and figure out how far you want to walk down this new hairstyle path. But at your next cut, really insist, even if your stylist tells you that this cut was quite severe!!!)
I also love the glasses on you. Even if they are not quite as large as you were envisioning, the style is modern, fresh, and different. Love both, prefer the red.
I agree that a bag inventory is a good idea -- would be nice to see you with something that has a more fluid or slouchy shape that feels more modern and plays in the space between tomboy and lady. With bags I think you can definitely find one that is a hybrid (perhaps not so easy to find clothing in the middle).

Congratulations on this evolution. It's really amazing to behold.

Following Angie's update guidelines has made a huge difference in your image! Somehow, despite the dark colours, you look younger/cheerier in #6-7 than in previous WIWs. I think it's the hairstyle & glasses. I'm amazed at how good this version looks, and excited to see where it goes as you fine tune!

Very late to the party, but wanted to say that I LOVE the hair. I love it as is,and I will love it with even for edge. Have you thought about adding any color? Like light blue or pale purple, like Nicole Ritchie or Kelly Osborne? Kind of punk, but softer?

Overall, I think you look amazing! Wow!
As for bag, my first thought was messenger bag, which I believe I saw as I scrolled through the responses. I personally love messenger bags so I am biased. But they feel... Stricter than slouchy hobos, minimal (no doodads or dangling bits), NOT ladylike. All of which work for me. I think they have to be nice leather though.
I'm not 100% on the docs. Are they new or used? Could the laces be changed? I'm not anti doc (although I don't think I'll be a reviver), but I think that these look almost unintentional here, like work boots. Some kind of tweak rather than plain black might help.

Wow - Thanks for all the comments! Here's a few responses.

Suz - I think you're on to something with too much black fighting with my natural coloring - I have to think more on that because I know you're right on it but I've also so very much enjoyed limiting my palette to black, white and blue. I'm going to have to figure out a good balance and good colors that fit.... And I love your idea that a better descriptor for my style - even than industrial - is rugged. I like it a lot and agree. And I'm pulling up Marley's posts in panel view to inspire.

Jules - you have me pegged. They're used Docs (I wanted vintage for the famed superior quality, and that they were made in England with thick leather. I'm not sure these qualify as vintage, but they are made with the thick leather and in England). I actually am attracted to Docs specifically because they look like work boots, and would have gotten steel toes if I'd found them at a price I was wanting to pay. These are in fabulous shape (no scuffs or cracking), and I'm pretty thrilled with them. But I totally get that most people don't want to wear work boots as a fashion item To me they totally fit with the 'rugged' descriptor that Suz suggested.

And Angie - I'm actually keeping both specs, but intend to wear the red as my main specs and keep the black for back-up.

I'll do a bag inventory and post sometime soon (might take me a week or two to get there - work is awfully busy at the moment, and we're also dealing with various fruit harvests).

Thanks so much for all your thoughts! This has been very helpful to me.