"Entry-level" designer?

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My first response is Coach, because it's a superb quality at a very reasonable price (even at regular price!).

If that's not your cup of tea, I echo the other posts to try Marc by Marc Jacobs, Juicy, DKNY. Check eluxury.com for sale items, and neimanmarcus.com, bergdorfgoodman.com.

Welcome and good luck with your search!
 
Hobo International and Furla both make great handbags in your price range. Zappos has a good selection of both brands. Also, a friend of mine who had similar criteria to yours just bought a Monsac bag that she is very happy with.
 
Maxx New York makes very nice bags, most under $300. Nordstrom carries a small selection. Zappo's actually has the best selection I've seen. Have a look at my little bag webpage. I have a nice brown and very nice green Maxx NY bag. I just love them! I got the brown for around $285 and the green was $150. Both were on sale.
The Bag Lady's Corner

I also love my Brighton bags, check those out too. They run $200 and up. Most are below $300. Very well made bags
 
I saw A LOT of really nice MaxxNY bags at Marshall's and TJMaxx today. I would definately check there. Plus they always have a lot of nice Italian leather bags there for good prices.
 
I personally adore Betsey Johnson and Cynthia Rowley bags. I just picked up the oversized Betsey Good Girl for $250 from Loehmann's and that's the most I've ever paid for one of her bags, and I don't think I've ever paid more than $150 for a Cynthia Rowley. Both designers have cute, interesting takes on bags and all the things I've bought from them have held up really well. I have a two year old CR canvas and leather bag that I use at least 2-3 times a week that still looks like new.

Loehmann's has a website that usually has cute Marc by Marc Jacobs bags, along with CR and BJ.
 
my bag addiction started with coach and kate spade so i would recommend those two. but i must say francesco biasia has some cool stuff, too that's within your price range. happy bag hunting!
 
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