I've chatted with a few other sissies over the years I have spent in the BDSM lifestyle and something that men have a tendency to miss that women tend to know all about is using contrasting shades and colors to accentuate certain outfits.
The traditional palette for male clothing, aside from those found on neck ties, is usually rather drab. Insert neutral or dark colored pants, a solid color or plain-ish print (using a neutral color for the print), neutral or dark colored shoes, and depending upon the situation, sometimes a neutral jacket (or suit jacket that matches the pants), a belt that matches the shoes, and a neck tie that matches the overall scheme of things but possibly containing several different shades that compliment and match the shirt.
On the other hand, women's clothing covers such a wide and vibrant palette of colors that when a sissy is going to be dressing himself, unless he has a guiding eye to help, there's a good chance he will fail to garner maximum effect, especially if his goal is to go out and be noticed.
Being able to spot different shades of a common hue is a skill that women tend to be better at than men, but it is a skill that can be learned if you pay close enough attention. Contrasting shades of a common hue will stand out more and if you are on an outing attempting to get some humiliating smirks and giggles, a light pink top with a matching dark pink skirt or pants will definitely stand out more and appear less like a jump-suit from a distance than having both items being the identical shade.
Clashing is a no no. I was forced to learn good matching by my ex, who would pick one item and tell me to dress around that item. I was punished if something didn't match, unless I didn't have anything else that matched it and in those cases I would find myself hiding a pink or lavender sweater under my coat out with her at the mall trying to find a matching mini skirt.
The contrast lesson was driven home a bit more firmly by my current Mistress after she decided to tie me up and take pictures of me. Her complaint was that she didn't like the white outfit accented with white fur or a pink outfit accented with pink fur since it didn't stand out enough on camera.
A couple of examples are pictured below.