Dressing Like an Adult: Shopping Strategies + Personal Style Development

Here it is. Everything we can think of on how to develop fabulous personal style and then make your wardrobe perfect for you on any budget!



Identify your body shape & coloring, AKA what looks great on you

After living with yourself for this long, you probably have some idea of what looks good on you and the things you should avoid, but let’s get really specific!

  1. See the Flatter Factor section in Lee’s last post—I won’t rehash here. She shares great resources on how to identify what flatters you, your body type and coloring! I must emphasize that learning which colors flatter me has had the single greatest positive impact on my wardrobe.
  2. Pull out the clothes you already have that make you feel particularly confident when you wear them. How would you describe them? Try to translate this into a general characteristic. For instance, “I love this shirt because it makes my arms look great.” This could translate into: I should look for more half-sleeve tops that will also make my arms look great.
  3. Similarly, identify the clothes that you love so much, you’re in denial that they’re worn out. Make sure you never run out of that.
  4. This will be discussed below, but the best judge of what looks good on you is a really honest friend or family member. Have this person close at hand!

Identify your style

You can have the best fashionista on the planet buy your wardrobe, but if her/his style doesn’t match yours, you’ll never wear it. Or worse, you’ll wear it and hate it. Clothes are supposed to make you feel fabulous- don’t ever forget that!

  1. Look quickly through several catalogs (grab them from the registers in any stores at the mall that attract you—Godiva doesn’t count) or Pinterest boards and dog-ear/pin your favorite outfits. Try not to think too hard. Do not look at price or worry what would or would not look good on you. The idea here is to follow your instinct.
  2. Look through photos of famously well-dressed people to find more favorites. This will help you identify timeless favorites (the stuff worth buying good quality to last a while). Coco Chanel, Audrey Hepburn, Grace Kelly, Jaqueline Kennedy, Marilyn Monroe, and Kate Middleton come to mind. I’ve even pulled some of my favorite looks from the 1910s and 20s.
  3. Even your friends can be guides. Identify specific outfits that your friends have worn that you covet!

Identify your budget

Asking yourself several questions and forming a budget will be the skeleton of your wardrobe quest.

  1. Do I have a bulk budget? Do I have a monthly budget? How much?
  2. What do I want to accomplish in how long? Or will this just be an easy-does-it ongoing project?
  3. What is the maximum amount of money I am willing to spend on one item? Everyone has a limit and it’s good to acknowledge this limit from the start to avoid any awkward moments if you shop with your “personal shopper” buddy.
  4. Along with answers to these questions, before you ever start shopping, have a prioritized list of items you’re seeking (more detail below). This list, along with your budget, should keep you on track during your quest: you will see your progress and it will be easier to be patient.

Know what’s in your closet FIRST

I know everyone loathes cleaning out their closets, but I promise your purchases will be so much more satisfying if you do!

  1. Toss the stuff that’s beyond repair or doesn’t fit or is just plain awful. I promise you only need two sets of yard work/painting clothes: one for warm weather and one for cold.
  2. Make sure you can see everything in your closet. If you need to store your off-season clothes to accomplish this, then do so.
  3. Follow Lee’s incredible advice to put outfits together with what you already have and document them for future reference. Most likely, you’ll realize that you really don’t need to do much shopping. Now your budget is happy!
  4. Now add things to your shopping list: items that are worn out and you want again, newly discovered styles that you want to add to your wardrobe, and finally, the basics….


Start with the basics

Once you’ve identified several things you love and look great on you and you’ve written them down (or pinned or scrapbooked your fav catalog photos), add in the basics that are missing. Last and most important, prioritize that list with #1 being the biggest priority on your list and the least important at the end. These are some basics I think should be on every list:

  1. One or two well-fitting pairs of jeans. This is something I believe in spending more on. I know too many people who buy ten pair of jeans that fit so-so because “they’re on sale,” only to let them sit in their closet with the tags on. If you save up and buy that high quality perfect pair, they will last longer, you will probably spend less overall, and you will feel fabulous all the time- because there’s no avoiding jeans.
  2. A black or gray or white pencil skirt. Because they go with any dress shirt and look fabulous on every body shape. Period.
  3. At least one pair of chino and one pair of denim shorts. Again, the better the quality, the longer they’ll last.
  4. A few colors of your favorite cardigan and/or blazer. First of all, if you’re a girl then you’re probably testy about temperature and constantly need to add or strip layers: nothing facilitates this better than thin cardigans. Second, cardigans are awesome looking with almost everything. If you find a brand, style, or store of favorite cardigan, buy a few colors of it! Did I mention it’s really important to know which colors look best on you?
  5. A dressy, casual, and in-between version of the plain white shirt. Having white shirts to layer or go plain are invaluable. I suggest starting with a long-sleeve white dress shirt, a short-sleeve white dress shirt, a plain crew neck or v-neck white shirt, and a white version of whatever is in style (ie the ruffle color I’m seeing this spring season).
  6. A well-fitting trench coat (mid-thigh length).
  7. Tall riding boots, black and/or brown. These are warm and sophisticated and can’t be worn too much during cold months. The bonus is that they go with both jeans and skirts. I can’t stress enough that real leather will last you so much longer and save you money in the long run.
  8. A pair of leather flats for summer and booties for in-between weather.
  9. One pair of versatile black or gray or nude high heels, and one pair of bold, colorful ones. The black heels are just safe and necessary, but the sassy ones are for sprucing up your plain pencil skirt or black dress. I highly recommend real leather for the pumps—they’ll last so much longer (and feel so much better).
  10. A good quality, flattering dress or two. Finding a great dress for some reason trumps wearing a good skirt/shirt combo. It shows particular triumph. This is where knowing your body shape/type is the most useful. Bonus points for silk. Unfortunately, most of my best dresses have been random, one-time finds. This one requires patience. Also, summer dresses will change your life–cool and classy and moveable!

Accessories go a long way

As I get older, develop more of a timeless taste, and build up my collection of good quality, lasting clothes, I’m realizing that most of the “meat and potatoes” items that show up in each new catalog are already in my closet. If you pay attention, you will realize that it’s the very little things that change often. You can save yourself a lot of money and still look “this season” by switching up the accessories (or hair, if you’re daring). And if you’re unsure about your ability to determine what is “this season”, looking at the catalogs again or just wandering the mall will tell you what is in style that five minutes. Here are a few examples and secrets to success:

  1. Sandals– not exactly accessories, but they completely change every year and can really sway the “look” of your outfit.
  2. Belts– thickness, colors, and material change constantly.
  3. Jewelry– obviously. Sometimes going ring-heavy is the thing, or lots of necklaces, sometimes it’s all about earrings, and so on. Jewelry will make the biggest difference in your look.
  4. Brooches and pins– I have been surprised at how often I use my favorite vintage brooches and they’re surprisingly affordable.
  5. Scarves– old school and never failing. Plaid or fair isle patterned for the fall/winter. Light, linen, and pastels for the spring/summer. The best thing you can do for yourself here is be bold. Girls seem to be afraid of scarves sometimes and get plain colors. What a waste! Plain and versatile is your coat/jacket’s job. Panache is your scarf’s job. (All the same goes for gloves).
  6. Watches
  7. Hair accessories
  8. Hats. This is my all-time favorite accessory and I have dozens, but many seem to fear hats. Whatever the reason for the terror, if you overcome it can take you far! If you want to start with baby steps, I suggest the beret. It’s classic, sophisticated, goes with everything, has never gone out of style (I’ve had mine for 20 years now)…oh and warm. And let’s be honest: Paris is always a good idea.


Before you do anything else, review Lee’s tips under “Ways to save on quality clothing purchases.” High quality clothing and shopping budgets are not mutually exclusive!

As often as I shop, I’m still surprised at how my senses go into overload when I enter a store–especially a favorite one. This is dangerous because the “I want all of it” attack sidetracks you from what you’re really looking for. Here are my tips for taking control:

  1. Never ever go into a store without your wishlist. This list can be vague or ongoing (mine is on my phone in Wunderlist), but the important thing is it reminds you of what you really need next, keeps you from feeling overwhelmed.
  2. Know your weaknesses. We all have favorite things to buy. If unchecked, I will buy eighty shirts and shoes to go with them, while my jeans fall to pieces. In contrast, I have a friend who can’t resist a cute pair of jeans, no matter how expensive or how many pairs she already has. Know what your tendencies are so you can wave your own red flags when you walk in a store. Force yourself to follow your list instead.
  3. Leave your wallet in the car. Try things on, take photos with your phone, then go home and see if you still want it in a week. I’ll even look up the items on the store’s website (this obviously won’t work for boutique shopping), pin them to a Pinterest board, and look back every month or so to see if I’m still interested. Either I’m over it or it’s now on sale. Win, win.

Take an honest friend

Preferably one whose taste you really like. Make sure you both know what you’re looking for and don’t leave the house without him/her making the following oath: I do solemnly swear to not let my bosom friend leave a store with anything she does not love or that does not look good on her. Cross my heart and hope to die. I think of this every time I look at my wedding photos because I adore my dress and came so close to not buying it. While shopping, I was seduced by a much trendier dress that, in retrospect, was not flattering. Luckily my mother, best friend, cousin, and even the store owner disregarded my feelings and insisted that another dress was perfect for my coloring and body shape. I was not convinced, but trusted their perspective. I cannot tell you how many times I’ve been so happy that I did.


If you can’t spend much time in the store

Whether you work during business hours or your kids are gremlins or you simply hate crowds, you may have a great reason to avoid stores. Here are a few strategies for you.

  1. Obviously, online shopping. How did people live before the World Wide Web? If you have a little time for brick and mortar store shopping, but not enough, I recommend the above strategy: browse quickly, try a few things on, take photos, pin, buy later online.
  2. For those who have the discipline (Lee rocks this strategy), buy lots of styles and sizes online, try them on in the comfort of your own home, and then return most of it. Again, if you have a little time in the store but not enough, it’s easier to return items quickly than to try everything on in the store with kids. Nordstrom is a great choice if you seriously never want to step foot in the store—free shipping and free returns. Always!
  3. eBay, or other online second hand stores (i.e.Thred-UP). If you know well how you fit in certain brands/styles and you know exactly what you’re looking for and especially if it comes from a mainstream retailer, eBay shopping will change your life. For example, I have a favorite pant from Banana Republic that fits like a glove. I know exactly the style and size, just needed a few more colors. A quick eBay search resulted in THREE pairs “new with tags” for a total dollar amount of less than one pair in the store. I could write a whole post on my eBay success stories.

Did we miss anything? Let us know in the comments! Happy spring and new wardrobe beginnings!

Also in the Dressing Like an Adult series…

  1. Why
  2. Demystifying & Simplifying the Capsule Wardrobe
  3. Solutions to Get Ready for the Day Faster
  4. Care & Keeping Solutions
  5. Quality Matters + The Flatter Factor
  6. Shopping Strategies + Personal Style Development
  7. BONUS: The Page I took from the Midcentury Housewife’s Book



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