7 Steps to Plan a Seasonal Wardrobe You’ll Love

While the weeks of transitioning from one season to another can sometimes seem a little frustrating weather-wise, they actually serve a beautiful purpose in wardrobe planning. This is the time to map out your wardrobe for the coming season so that it is enjoyable, functional and stylish. Today I’m walking you through 7 easy steps to plan a seasonal wardrobe you will absolutely love wearing.

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As I’m writing this blog post we’re heading into fall. But these steps work for whatever the next season is on your calendar. My goal is to help you create a functional, beautiful wardrobe that makes getting dressed for your day easy and fun. This post is part of our Define Your Style…Refine Your Wardrobe 2024 style series. You can always find the other posts in this series through the link in the top menu or here.

Step 1 – Evaluate your wardrobe needs.

Well, that sounds basic enough…but also very vague. Let me explain. As you begin to think about the wardrobe you want to wear for the coming season, first evaluate the kinds of outfits you will truly need. Remember, here at Dressed for My Day I stress that we want to build a wardrobe for our real lifestyle, not the one we dream of or the one you may have just retired from (lucky dog!), but the life you’re really living.

And don’t just think about the kind of clothes you think you need for your real lifestyle, but more specifically consider the types of outfits you’ll be wearing. Look at your calendar and think about the activities you’ll be doing. Will you be hiking, antiquing, traveling, volunteering, taking care of grandchildren, caring for aging parents, working, attending women’s events, going to church, working in your yard? We don’t just want to get dressed for our day when we have something out of the ordinary to do. We want to get dressed for the everyday days, so lean into those as you consider your wardrobe needs.

• Activity: Take just a few minutes to look through your calendar and jot down a list of activities you’ll be doing. Then make another list of the types of outfits you enjoy wearing for those activities in the upcoming season (such as “skirt, tee & denim jacket” or “stylish jeans & sweater with loafers” or maybe “dress with knee high boots”). Think outfit formulas that work for you. And be specific about the items you’ll need to make those formulas work, such as belts, shoe types, bags and jewelry.

If you need a little more help considering your real lifestyle, check out the blog post Define Your Style for Your {Real} Lifestyle.

Step 2 – Consider the current styles.

One of the ways we women of a certain age can continue to look relevant, interesting and our most youthful is to stay current with our style. That doesn’t mean you have to jump on board with every trend that blows through town by any means. In fact, adopting too many trends can have the opposite effect, causing us to look less self-confident, a little desperate and immature. At this point our style should be a well-seasoned, so to speak. We want to look a little “settled into” our style, but also current and in-the-know. It can feel like a bit of a tightrope, but I think the results are worth the effort.

I encourage you to definitely stay true to your personal style, what you love and what makes you feel authentic and confident. But also choose a few of the most current trends that also genuinely resonate with you and incorporate them into your outfits. This year so many fashion classics are trending, making it easier than ever to be on trend but also true to a more traditional personal style. You might consider adding some leopard print, metallics, splashes of red or lacy details to your outfits. Or you could sport some slingback pumps, ballet flats, relaxed fit jeans, wide leg trousers, a chunky cashmere cardigan or a cropped or fitted blazer – all classics with staying power.

• Activity: Check out my recent Fall Trends Week blog posts to see some of the current trends that are most wearable for women over 50. You might start here with Fall 2024 Fashion Trends to Wear Now. Also watch Fall 2024 Fashion Trends Most Wearable for Women Over 50 for additional ideas. Then make a short list of style hacks, accessories, color choices or garments that you’ll add to your wardrobe this season for a more updated look.

Step 3 – Re-evaluate your personal style.

If you’ve been following along with our 2024 style series to this point, you’ve probably already defined your personal style with three style angles. See the graphic below to refresh your memory. And if you haven’t yet defined your personal style with three style angles of your choice, I suggest you check out this blog post, How to Define Your Personal Style.

But those three style angles are not chiseled into stone; you have the freedom to change them at any time. And I always feel like early fall is a time of new beginnings. So this is a great time to re-evaluate your personal style. How are those style angles working for you? Do they feel comfortable and fit your personality? Are you enjoying building a wardrobe and outfits based on them? Or do they feel like a prison locking you into something that no longer feels authentic to who you are?

• Activity: Think back over the past week. Have the outfits you’ve worn and enjoyed reflected your three chosen style angles? Better yet, if you have them, look back over photos of outfits you’ve worn recently. Do you look authentic and like the best version of your true self in those outfits? If yes, move on with joy. If no, reconsider those three style angles. The possibilities are endless!

Step 4 – Choose your color palette.

I absolutely think it’s a great idea to have your colors analyzed to find out what hues look best on you. In fact, if it’s been a while since you had that done, you may want to do it again. Our coloring definitely changes as we age. But while I think a color analysis provides you with invaluable information, I don’t believe that’s where you should stop when it comes to your wardrobe.

I’m a proponent of building a seasonal wardrobe with a limited color palette – one that YOU limit for yourself. When I fill my closet with every color that I can wear, I easily get frustrated when I try to create multiple outfits from those items. I prefer a closet with fewer items that easily mix and match rather than one filled with clothes in every color of my personal rainbow. It makes getting dressed so much more fun and easier.

By the way, that doesn’t mean that everything I have in, say, berry red will mix and match and be worn together. That would be really tricky in my wardrobe. But it does mean that everything that I can wear with one berry red jacket can probably also be worn with another berry red jacket. Make sense? Plus, I just know how to work with those colors; I become an expert at wearing them. For instance, I have the right lipstick and jewelry to make them sing. And I can paint my nails a color that works with everything in my closet.

So I always recommend that we select 3-5 neutrals we’re wear for a season and 3-5 signature colors we’ll have in our closet for that season. And hey, if you occasionally allow a rogue color into your wardrobe, no big deal. You’re in charge here! But limiting my color palette actually helps me to shop more strategically and helps me to “stay in my lane” with my personal style.

• Activity: Take the time to make a list of the 3-5 neutrals and 3-5 signature colors you’ll wear this fall. I generally choose colors for fall and winter and then a different set for spring and summer, but you do what works for you. Make a graphic or picture of the colors and keep them in your phone for easy reference. You might want to check out the blog post Define Your Style with Colors & Neutrals for additional insights.

Step 5 – Set your budget.

It’s important to most of us to build a wardrobe that authentically reflects our personal style and works for our lifestyle, but also stays within our financial means. Nothing is more miserable than looking at a closet full of clothes that you went into debt to purchase.

So definitely don’t skip this step. Set your budget for replenishing your seasonal wardrobe before you start looking at catalogs and websites and store displays.

I’m frequently asked what a woman over 50 who is on a set income should budget for clothing. I honestly can’t tell you. I even asked my brother, who is a financial coach, to share his opinion, but he had no crystal clear answers. He did say, however, that clothing is one of those budget items that many people underestimate. His advice is to “get real” about all of our budget line items. Otherwise we run into problems and start robbing from Peter to pay Paul.

I also think it’s wise to establish a clothing budget that works for you and your spouse, and then stick to it. I’m often asked about my personal clothing budget, but let me remind you that purchasing clothing is a business cost for me. That doesn’t mean that I get to deduct very much of it for tax purposes, mind you. But I purchase my clothing out of my business budget, not our household budget. Showing clothing options is what I do for a living, so I have a wardrobe that I keep for myself year over year, and then I have many more things I pass forward to others after I’m finished sharing them. No one really needs all the things I share here or on YouTube. I certainly don’t. I’m actually looking forward to the day when I retire and no longer have clothes filling up three closets!

• Activity: Well this is obvious. But take the time to establish a budget for the season. I prefer a seasonal budget rather than a monthly one for clothing. That way I can be more strategic about sales and special offers, such as Labor Day weekend and Black Friday weekend.

Step 6 – Shop your closet first.

As you plan your seasonal wardrobe, don’t head to the store just yet. Shop your closet first. For instance, if you’re loving the splash of red that everyone is adding to their outfits this year, see if you have red items you can use already in your possession. Maybe a red shoulder bag, shoes, hat or sweater.

Or if you’re wanting to wear the modern denim, see if you already have a pair of wide leg, flares or straight leg jeans from last year that you loved wearing. While these silhouettes are trending, not that much has really changed in denim from last year. So if you caught up with the trends last year, you’re probably good to go.

For instance, I was certainly tempted to buy new ankle length wide leg jeans this fall. But the Madewell wide leg jeans above from last year are still on trend, so I’m sticking with them. There’s no need to use your budget buying duplicates of things you already own and love.

• Activity: There’s no way around it. Before you start purchasing new things for fall, I highly recommend pulling your fall and winter clothes out of storage and assessing the situation.

Step 7 – Prioritize your outfit makers.

Yes, this is the final step of planning your seasonal wardrobe, then you get to begin shopping…if you wish. When we start shopping for a new season I think it’s smart to prioritize some purchases over others. That’s a great way to stretch your budget for more impact and fewer regrets.

I recommend prioritizing outfit makers. These are those pieces that add personality, style, interest to your outfits. They’ll set you apart and bring you joy, too. Yes, you absolutely need some basics, but my bet is that you have more of those already than you may think. If not, definitely stock up on a t-shirt or two, a great pair of jeans (or more if you wear them frequently), a wear-everywhere dress, a trending denim skirt and a good pair of trousers or three.

I like to make a wish list of the outfit makers and really pursue them. I check my favorite brands to see what they’re carrying, but I also scout out others before I choose the one or two I love. These are personality driven pieces, so make sure they align with your personal style and really “tell your story.”

How many outfit makers do you need? That’s really up to you. I like to wear mine frequently and have no problem, for instance, wearing one stunning blazer multiple ways for a full week of travel. So I’d just recommend having enough outfit makers so that you can easily add some polish and pizzaz to each outfit. These don’t have to be expensive or even investment pieces, by the way. I recommend high-low dressing, creating outfits from a mixture of investment-worthy pieces and those I found on sale or at a bargain store.

Let’s say, just for the sake of having a starting place, you want a dozen different outfit makers that you can weave in and out of your outfits during the upcoming season. I suggest some of those be completer pieces, such as jackets or cardigans, a couple others be accessories and the remainder be either statement tops or one-and-done dresses, depending on your personal style.

• Activity: Spend some time looking through the catalogs of your favorite fashion retailers to see what outfit makers they are highlighting. Which ones strike you and seem to resonate with your personal style? Do you already have similar items in your closet? Throw those into the mix first. Then begin shopping for the additional statement-making items that will make your wardrobe fun, interesting and stylish.

Don’t forget to check out other blog posts in our Define Your Style…Refine Your Wardrobe if you haven’t already. You might want to begin HERE.

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next up, 7 Tips to Make Your Wardrobe More Enjoyable (click to access)