Decide on Formality
Usually the event invitation will clue you into the formality of the event, whether it’s casual or black tie. But sometimes even that will cause confusion (short dress or long?)
In general; the later in the day the event (after 6 p.m.), the dressier it will be. Long dresses are usually reserved only for formal occasions. at the bar
While some fabrics are year-round — silk, brocade, organza, jersey — fabrics like velvet and gold spangles are best reserved for winter holidays.
2. Flatter Your Figure:
The most important feature of your new sissy dress is how well it flatters you. Remember; that darker colors and simple cuts (a sheath, an A-line are the most flattering for the TG figure).
Show off your best feature. If you have gorgeous eyes, then play them up with beautiful makeup, off-the-face hair and jeweled earrings in a complimentary shade.
Not sure what your best asset is? Ask a friend or significant other. Or go to a store that sells special occasion dresses and enlist the salesperson’s help. However, most TG women like to cover their shoulders, and show their legs!
Choose a Color
You could just wear a little black dress (classy, flattering and slenderizing), but why not explore some of the other dressy options? Red, bold prints, even gold are dramatic enough for evening wear. Pastels, mid-range brights and soft prints look great for dressy day occasions.
Blue (from navy to royal), pink (from cotton candy to fuchsia) and white (from candlelight to cream) look great on almost everyone. Remember that the “Don’t wear white to a wedding” wisdom is still considered a fashion don’t by most transgender women.
Pick a Style:
Catalogs, the internet and magazines are great places to seek special occasion cross dress inspiration. Instead of going with something trendy, try to find a dress that reflects classic, timeless elegance. Remember that you’ll have to look at photos of you in the dress for years to come.
Classic special occasion dresses are often deceptively simple, but they usually let the beauty of the wearer shine through. A few examples: the little black dress (aka the cocktail dress), a goddess gown (draped and rouched), a ballgown, a slip dress.
Shop
Set a budget before shopping. Special occasion dresses usually cost more than $100, but if you comparison crossdress shop you can find one that works in your price range.
Shop secondhand stores and sales to save even more money on a dress. If you shop in a store, dress for the day by bringing along heels, any special accessories you know you want to use and a strapless bra.
When shopping online, make sure you understand both the sizing (know your measurements and check against a size chart on the site) and the return policy (some stores don’t take returns on dresses.)
Special Occasion Dresses
Accessorize
The trimmings will take their cue from the dress, but for special occasions your jewelry usually gets bigger and your bag and shoes get smaller (as in strappy sandals).Although you may want to add tons of glitz, remember that you can kill a look with too much matchy-matchy accessorizing. Find earrings, necklace and bracelet that complement each other without being a matching set.
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If your legs aren’t perfect enough to go bare, and you need camouflage and you don’t like to wear leg makeup, then opt for super-sheer hose or fishnets.