Where to shop
Actually getting out and buying a bra for the first time is an interesting experience. A little planning can go a long way to making that trip a fun and productive one.
Catalogue or on-line shopping: This is the easiest method for the timid, but proper, comfortable, natural-looking fit requires some trial and error. It usually involves ordering a number of bras around your size, then returning those that don’t fit. Read the fine print to make sure they can be returned; some undergarments can’t. Sears has a very wide range of styles, including many large sizes. Most on-line (Internet) shopping sites are American; don’t forget about the exchange rate! Follow their measuring instructions carefully.
Thrift stores (Value Village, Salvation Army etc.): These usually have a rather limited selection, usually of fancy items. Most items will not have size tags, so finding (or learning) your size can be difficult. Trying on is possible.
Low-cost department stores (Wal-Mart, Zellers, etc.): These stores’ prices are usually reasonable, but staff is not always helpful so you need to know exactly what you want. The open-air layout may be intimidating. Stores are least crowded early or late in the day, most crowded on weekends. To avoid crowds, avoid sale days. Trying on is rarely an option unless you’re comfortable shopping en femme.
Department stores (Sears, The Bay etc.): prices are higher, but selection is usually good. Most make a point of stocking every size in every style. Department layout tends to be more enclosed. Staff tend to be more helpful, but you need to know your size. Few department stores will allow you into the fitting rooms unless you’re en femme, although you can sometimes discreetly try on your prospect in the men’s fitting rooms.
Lingerie specialty stores (La Senza, Petticoat Box etc.): These are nice, well laid out stores that carry a wide range of sizes and styles. Some, like La Senza and Victoria’s Secret carry only their own brands. Staff are usually helpful and not bothered about why you’re buying this stuff. Some stores will take appointments and will allow trying on at those times; others are less accepting of crossdressers. If in doubt, phone and ask to speak with the manager.
Mastectomy stores: These stores cater to mastectomy (breast cancer) patients and therefore carry styles designed specifically to work with breast forms. They may also carry specially-designed swimwear and other lingerie. They will take appointments and take the time to fit you properly. Staff are qualified fitters and have the expertise to fit a bra for breast forms, though not all may have worked with a crossdresser before. Expect to pay a premium price; you’re shopping in a specialty store and receiving expert service.