Ready? Good! Let's jump right in...
The Frame Style (the bike's geometry) is an early decision you make towards finding the right bicycle for you. I ruminated on this topic; Just how much do you need to know to buy a new (Euro Style) Bicycle Part I. My recommendation is a bike with an Up Right geometry, the Sit Up & Beg style or as I like to say the Euro Style bicycle. You may also want to consider Cruisers or Townie bicycles which are distant second cousins, technically speaking. I suggest reading Sit Up & Beg - Most Ergonomic? Then for further info & answers read Sit Up & Beg - Most Ergonomic? -- Good Answer. I highly recommend (for the greatest of ease while riding in dresses and skirts) a step-through frame and also simply called a 'ladies' frame. Size matters, so getting the right size for you is the other half of the equation. Be sure when you get to the point of actually buying your bicycle to consult with the seller and emphatically and absolutely determine that you are getting the right size bike!
Your next decision is whether to buy vintage or new?I started off choosing vintage for a variety of reasons. I always like to buy recycled (anything) first. I also think steel frames are far superior to any 'Big Box' bikes manufactured out of China. For the same ballpark $200.00 you can get a real vintage beauty, but you need to know a thing or two before jumping in and buying off Craigslist or Ebay. For some tips on buying read; Buying a Vintage Bike Guide along with reading about my own personal experience rebuilding a vintage bike; Finding and Rebuilding my Motobecane Bicycle. Price points, oh yeah the other determining factor. Not much cash? Ah, well choosing a vintage bicycle is the way to go. Read about how overwhelmingly popular vintage bicycles have become; Vintage Bikes - Girls want them! If you're looking for a NEW bicycle then be sure to check out this posting;12 Bicycles for Girls. Recommendations are across all price points, high to low.
The next big decision is going to involve how you plan to use your bicycle? Plus where do you live? Your answers will determine how many gears you'll want. General rule of thumb is 3 gears minimum. Flatlanders, strictly leisure riders, incredibly short distance bike commuters, and all those super fit fixie riders maybe be able to get away with a single speed. I have a single speed cruiser I ride to the beach and up the block to my neighborhood shops. If your terrain includes hills, then get multiple gears. Talk to anybody you can find who bike commutes in your area and ask how many gears they think work best. Now would be a good time to get friendly with your local bike coop, community bike advocacy groups, and your local bike shop (LBS) who you'll probably end up buying bike stuff from any way.
The Let's Be Lady Like! check list: Of course now that you plan to wear all sorts of stylish outfits while riding your new bicycle, then you'll want to make sure your bicycle has fenders, a skirt guard, a fully enclosed chain guard to keep you and your clothes free from dirt and grim. If these are not already included with your bicycle, it is possible in many cases to add them on later.
The Practicality check list: You will want a front basket, rear rack, and panniers (you add those onto that rear rack), for transporting your stuff, be it groceries, Chinese take-home, library books, you get the picture. Additionally there is a very possible extra benefit, you will earn respect and street cred amongst the utility and commuter cyclists!
The Safety Items check list: Lights, reflectors, bicycle bell, bicycle lock, and a helmet if you chose to wear one (I advocate for helmet safety). You could also add in a bicycle repair kit for fixing a flat tire in a pinch.
The Purely Aesthetic and Stylish checklist: Well this could get cross referenced to several of the afore mentioned items above. I'd add cork handle bar grips (cork is a sustainable and eco material). Also a Brooks saddle would be wonderful! And you can shellac those cork grips to match the patina of your Brooks saddle whether it's it vintage or new. Other considerations...Add streamers you make yourself or check ETSY, perhaps a bicycle basket liner, and pretty flowers for your basket (as in brightening up any dreary winter's duldrum day).
Sincerely hope you've found this posting and it's check lists helpful! Happy Bicycle Riding to All the Stylish Lovelies!!
Newer posting and highly recommended... 'Dream Bicycle List - Let's Go Shopping'.