Pick a base colour. Brown, Navy or Black will work for this-but stick to it for now. It will make things much easier. Black is probably the easiest to find.

In your base colour, you should look at sales, thrift stores, mom and friend’s cast-offs-everywhere! and acquire the following:

-Classic cut trousers (not trendy-no studs, no frills, no cutsey belt. Just plain. Make sure they fit.
-Low heels with closed toes
-Classic cut skirt-at least to the knee. Make it flattering-an A line might be great on one woman, a pencil might be nicer on another

Then you should evaluate what you have and try to find the following if you have gaps:

-1-2 cotton blouses. One should be white, the other should be in a colour that flatters you and matches your basics. No prints, no embroidery, no fuss!
-1 sweater that coordinates with all of the above and that can be worn over the shirts. Cardigans can be nice to being with.
-1 dress that is cocktail length. Its nice if the sweater can go over it. It shouldn’t be too ’sexy’ but shouldn’t be dowdy either.
-4-5 shells/knit tops in varying colours that flatter you.
-1 pair of nice jeans
-A jacket-probably hip length, classicly cut as if for a suit. Thrift shops are great for these. It can be paired with nice jeans or with your base pieces.
-2-3 scarves These should match most of what you have. You should have one small one in a silky fabric that can be tied with an open collared button shirt, one larger one that can be used as a wrap with the cocktail dress and possibly and alternate. They can keep you warm, dress things up and really add to that ‘pretty’ feeling.

To build later:

-Something you can wear to a funeral, something you can wear to a wedding, and something you can wear to a party. They are probably three different somethings-but you should always have them on hand and make sure they still fit and are in good condition every six months. These things tend to creep up on us!
-A pair of boots in the base colour can keep you warmer in winter
-Flats in an exciting colour can dress things down
-a girly dress that is appropriate for weekends
-A series of cotton skirts that are multi-seasonal and match your knit tops and sweater
-Start over with a new base colour
-1 pair of comfortable sandals

Anyhow, you don’t need to go to thrift stores or anything if you don’t want to. I buy all of my clothes brand new, just mostly on sale. (Of course, the thrift stores aren’t stocked with many goodies around here like some.)

I frequent Macy’s website, and they have pretty good sales for some nice, quality stuff that’ll last. (Like the wool Pea Coat I’m fawning over right now.) Of course, most of my clothes come from Abercrombie… But I have seen some great things on Dillard’s sales racks and Banana Republic as well. (No Macy’s store here. :()

Unfortunately, my $300 Coach bag opened me to the world of designer things, and I’m a tiny bit addicted to adding them to my wardrobe, one piece at a time. My last splurge as far as clothes go were my Ugg boots I just ordered. They should be here tomorrow, so I’m hoping to get a pic of them up on my blog then.

I wish I could remember which blog it was, but someone recently wrote a post called “All icing, no cake” or something similar about how you’re supposed to have mostly staples and a few frilly, in-season stuff. But mostly classics that don’t go out of style.

That said, if you’re near a Marshall’s, I love them for labels for less. I got a Kenneth Cole Reaction shirt for $15 there. It’s gorgeous. I’ve also found slightly pricier labels like BCBG for $15-30 (the $30 was a dress, suggested price was something like $190!) It’s sort of an ongoing effort wherein you have to pick through things. (If Marshall’s isn’t in your area, try something like Filene’s Basement or Ross, which also carries some of the designer names.)

Of course, pick through Goodwill, as suggested. Sometimes you find things with tags still attached.

Old Navy has really revamped its line from what I’ve seen (and I appreciate that they go from size 0 all the way into the 20s — I’m a 14 but it’s nice to see some realism these days). The prices are still pretty good on a bunch of items, though. And some of the stuff is very feminine - without being overly “girly.”

But my favorite trick, if you’re just not sure what you should be looking for, is to go to a higher-end store like Nordstrom. I dragged my mom there once or twice to get someone else’s opinion. They suggested some fabulous stuff (and she even bought a couple lower-end items). But most of it we filed away in our heads and then we went and found the staples much cheaper.

Also, don’t forget the outlet stores. Even then, there will be stores not to bother with. But some of them have fabulous clearance prices. If you’re not too far from one, it’s good to make the occasional foray.

And Gap clearances new stuff every Sunday. So shop there each Sunday to get first pickings. I once got a pair of overall shorts for $15.

If you feel bad about making the Nordy girls work when you’re not going to buy anything, you can always buy one small item so they get some kind of commission. But overall, most women spend there pretty fluidly so I don’t really feel bad when I use this method. Because one day I will go back and spend some money there for real, because they’ve been so helpful. And because their return policy is fabulous.

Chadwicks also has a great clearance section - check it out too.

These will get you through. I shop at consignment stores mostly and get a good brand name for a low price. But if you’re going to invest, might as well be in footwear.

Found your blog off Sense to Save. I’m psyched and will be reading it again!

This is a great challenge, my wife tried doing something very much like these after watching a TV show that talked about “fundamental items” to build a wardrobe around.

My wife took that list and shopped at thrift stores, gradually building up the fundamental items that let her leverage her existing wardrobe.

Anyway, if you want to read the whole story, just follow the link to our blog and search for “The Goodwill Fashion Challenge”.

-Paul