Halloween is the first in a string of holidays that offer an opportunity to dress up. You might drag a costume box out of storage or you might put on a black dress and buy a pointy hat at a thrift shop and call it good. The trick-or-treat season is a good time to get winter-weather and winter-party ready in the clothing department.
Your body might have changed in the year since you last put on your party pants or favorite LBD. Even if your weight is exactly the same, things shift around and what looked great last year might look ill-fitting this year. Trying things on is essential for making decisions.
To keep it fun, maybe start with all your fiesta-wear. If you tend to not finish projects though, you should start with your day-to-day tops and move on to your day to day bottoms and save the velvet, silk and sequined stuff for last.
Take out one category at a time. Anything you’ve worn recently and love leave in the closet. Anything that hasn’t been worn in a while needs reassessment. With tops, you will need to try it on to see if it’s a “keep” on its own. If so, then you will need to make sure it has at least one bottom half that works with it. Regarding bottoms, skirts can be irritating in that finding just the right top is often difficult to impossible for some reason. If you have anything that stays on the hanger because it’s never found quite the right other half, let it go.
As you try things on, note what you like or dislike about each item so that next time you go shopping you won’t have to waste much time trying on things that won’t flatter you. For me, I can no longer wear anything tight around my neck—it just accentuates the sagging. Pant shapes come and go. I thought I was a “skinny jeans forever!” person, but I am loving the comfort and more age-appropriate look of wide leg jeans.
As you put outfits together, when you find a combination that you really like, snap a selfie in a full-length mirror. I have made iPhone photo albums as well as printed binders full of these types of photos for clients so that when they can’t decide what to wear, they can flip through these photos to remind them of some of their best options.
Make sure you have what you need to stay warm and dry this winter. How is your go-to rain gear looking? Do you have a warm coat that works for every day? Do you need to replenish items in categories like wool socks, gloves, scarves, cardigans or headgear?
For parties, are you ready with a last-minute, always-looks-great” outfit? Do you have the right shoes, the right tights or hose? Spur of the moment shopping for a special occasion almost always results in buyer’s remorse. Have at least one outfit ready that works for a variety of occasions. For women, a simple black dress works for almost any party. Depending on your shape, sheath, A-line or fit and flare are versatile styles to dress up or down with accessories, tights and shoe choices.
Now’s the time to consign any winter looks that no longer suit you. Create a little room for a new item or two. And always remember—never buy a skirt unless you are certain you have a top that goes with it.