Mirriam Webster's definition of 'well- heeled' : having plenty of money.
There are a few things that are always necessities when it comes to personal image- I would argue maybe more so when you're a bit broke. Whatever your current financial situation- whether or not you're in the position to buy new goodies, you need to have reliable, good shoe repair, a good hair stylist, and even if you have some sewing skills, a good tailor as well.
Why is this important? When times get tough it can become trickier to look your best- so if you've done right by your wardrobe and invested in regular upkeep thus far you'll be in the best position possible; when you can't afford to replace the basics or update with some more on-trend pieces all you'll have to do is continue with the minimum maintenence. Yes, you'll be spending some money- but it should only be a fraction of what you'd invest in entirely new pieces.
If, for example, you really need new shoes, but it's not going to happen right now, the next best thing is to have a great shoe repair person. This is crucial no matter what. Ratty looking shoes ruin an otherwise good outfit faster than anything else. You can't fake the shoes. That's where the term 'well-heeled' comes from- someone who's shoes are always in good repair. My shoe place- http://shoerepairburbank.wix.com/victorsshoerepair - takes The. Best. Care. of my shoes, boots and purses and makes them look like new each and every time I bring them in.
Say you have a great item of clothing that's in good condition, but is somewhat out dated to the point that you don't really want to wear it; figure out if perhaps there's something that can be done to bring it more up to date or towards something you'll love and wear- if so then trot it down to your tailor and see if they can make it a reality, and how much it would cost. It's free to ask, right? (If not, find another tailor.) I'm currently looking for a new tailor- my last one got robbed and they took my skirt (??!)….can't say I was terribly attached to that skirt, but still, it put me off….
As I'm always pointing out, you'll be better off investing in fewer, less expensive pieces that you have tailored to fit you properly than spending all your money on fancy, trendy stuff that doesn't fit well.
And the last thing- a good hair stylist- I don't think I need to say much here. A great stylist will find the cut that flatters you the most and will work with your preferences- and I don't know about you, but nothing- NOTHING makes me feel like I look my best more than a great haircut. If you can find a great stylist at Supercuts, good for you- stick with them. My experience has been that they let you call ahead and schedule with a particular stylist. Another option to consider is going for a very simple cut that should be easier to get done well at more places.
If you care about how you look then these things are always essentials. If you're broke or close to, they can get adjusted down to just bare-bones maintenance. When you're in the money they should still come first before buying new anything- that way should your bank account take a down-turn you'll just have to spend the minimum for upkeep, and still look like your most fabulous self.