Learning how to shop for myself is an ongoing process and education. Below are the tips I use to stay on track.
You are not me, you are not any blogger or celebrity or person in your neighborhood, no matter how relatable or similar that woman may be. This is a GOOD thing, we women are snowflakes not only when it comes to body shape and size, but coloring, personal style, lifestyle, and temperament. So when you see something great out there you need to say (and sometimes you need to say it out loud), okay it looks great on her but would it look great on me? Does it make sense for me and my current life and wardrobe? This isn't covering the blogger or model's head, it's being completely honest with who you are, knowing and embracing your current self and situation.
What gets the most wear and why? Do you keep wearing that sundress because it's comfortable? Because it covers what needs to be covered running after kids yet doesn't cause you to overheat? Because the color or print makes you happy? Because your partner said you look pretty in it? There is no wrong answer, but delving into the why can help you figure out what NOT to purchase in the future and truly assess your current situation.
Do you regularly get dressed in the morning and wish you had a pair of nude pumps, a navy cardigan, a white blazer that fit well? Do you find situations where you wish you had an LBD on standby or will be attending a destination wedding and need dressy flat sandals? Don't just think about what you need, jot it down and put it in your wallet or purse. Stick to this list. Remember, you are you now. Don't shop for the old you, the future you, or the fantasy you. Shopping when not being realistic is the quickest way to waste money and lose any personal style.
If you only shop when you have an event on the calendar, you will be shopping in desperation having to buy something ANYTHING. And that something will likely only be worn once. Be prepared. Look at your upcoming social and career calendar, look at your past, and factor in what may happen. If you know you have a public speaking engagement once a year for work, be ready with a perfect suit that can look different each time with a switch of shell and accessories. If friends are getting engaged this year, begin looking for wedding, shower, and bachelorette appropriate dresses and outfits. I believe a not-so little black dress is a smart investment because it ensures you're ready for that unexpected funeral, wedding, cocktail party, luncheon, and can even be the base for many a costume for Halloween or theme nights. I actually have a list I made a decade ago of wardrobe staples that is a good starting point - adjust for your life and style but do factor in what may come down the pike.
I find it strange that the most pinned images from my blog are those of big and colorful closets and they are pinned on boards just of big and colorful closets. Don't try to make your closet pretty, a pretty looking closet usually equals a lost personal style. I know, I've been there. The more varied and exciting your wardrobe, the harder it is to get dressed and the more of a need to buy more to make everything work.
I've had readers complain that it seems everything I buy is from Gap, Ann Taylor, LOFT, and Nordstrom. I do this for a reason - it makes my life easier. These retailers carry petite and up to 14, they have free shipping promotions, and either have free return shipping or have a location near my home or office where I can drop in and return what doesn't work. I know some people will Google a type of garment and search for it or go blindly to the biggest mall in the area, but I find doing either sends me down a rabbit hole, leaves me sweaty and overwhelmed, and usually ends up emptying my pockets on things I don't need. There is nothing wrong with shopping at the same retailers all the time if they fit your figure, your budget, and your lifestyle. Life is short, don't spend it getting overwhelmed and frustrated at the mall or in front of your computer.
We're all short on time, but taking care with your closet (and drawers and jewelry boxes) will save you time and money in the long run. Carefully hang everything on hangers all facing the same direction. Organize your drawers so everything is visible. A place for everything and everything in its place so you can clearly see what you have, what you need, and what would improve the current wardrobe. When I start feeling the need for new clothes, I step away from the laptop and step into my closet to reorganize. Touching the garments, carefully buttoning and smoothing, organizing by category (I put all dresses together, all tops, all pants, etc.) and removing that which is damaged, doesn't fit or isn't appropriate to the season or your life keeps you connected and helps you really know if you need to shop and what you actually need to buy.
No dress will transform your life. A well-fitting pair of pants won't make you look 10 years younger and 20 pounds thinner. You'll make your ex seethe with jealously more by having a blast on the wedding dance floor than wearing that dress you searched three months for. While it's important to dress with and for respect for an interview, if a job won't hire you because your suit is three years old or your pants and blazer don't perfectly match the company likely won't be a happy fit in the long run. Clothing should be used to keep yourself from getting arrested for indecent exposure, to represent your emotion or intention. And to express who you already are. Money can't buy happiness and clothing can't change you. If you're looking for a big change, look within before opening your wallet.