A seasonal shopping approach for people who hate the term "shop strategically"

this one is chock full of inspo for fall

Every season, I like to take time to collect inspiration, study what others are wearing or have worn that is inspiring me, do lots of window shopping, and take stock of my own closet to prepare for the season ahead.

This practice, which I’ve been developing year-over-year and season-over-season helps me think clearly about what I have, what I want, and what I’m actually going to get dressed for. It’s important to me that I am smart and thoughtful about the purchases that I make (because taking my time and thinking things through almost always yields the best purchases), but I also don’t want honing my style to feel like no fun (this is, by the way, all supposed to be fun and make us feel great). I love a good spreadsheet when it comes to my day job, but at the thought of taking spreadsheets and analysis and cost-per-wear and record-keeping inventories of the things in my closet, my eyes start to glaze over. When I say I try to “shop smart”, I mean:

• I want to spend my budget thoughtfully

• I want to avoid having many multiples of the same type of item (eg: just say no to yet another grey sweatshirt)

• I want to do everything I can to avoid the feeling of “I have nothing to wear”

• I want to actually wear the clothes that I buy (eg: buying for the life I am actually living), and get great use out of them

• I want to have a closet full of things I love and that bring me joy

Doing this requires some level of planning & thoughtfulness, but also has to leave room for the inevitable impulse purchases (some will be great, some won’t, that’s okay!), and allow me to lean into retail therapy and make emotional purchases from time-to-time. I’m cool with that. I’m not cool with a million tabs open on my computer, being overwhelmed with options and getting a panicky feeling like I just NEED to buy something, not being able to make (mostly) clearheaded decisions about whether or not I really love something and not being able to keep track of my purchases or whether or not I already have something that is really similar in my closet.

The approach I take, in it’s most simplified form, involves 5 steps, three of which are essentially a continuous series of steps I am always going through. I’ve outlined the steps below, and I’ll share the output of steps one and two with you today!

The steps:

1. Collect inspiration - I really like Pinterest, both as a source of inspiration, as well as a place to organize purchases, and I make a board for every season. It doesn’t stop there because I also take an insane amount of screenshots and have a stack of magazines that I reference regularly next to my bed, and have an uncontrollable number of instagram saves. Most recently, I’m really into Zeen, which is moodboard & collage focused. Lots of inspo - makes the next step extra important.

2. Let it settle a little bit & mull it over - this is why I’ve needed to let myself delay really getting into fall - I need time to not just see and collect things that catch my eye, but also to digest those things and think about what I really like about them, what are the themes, where are there specific pieces, vibes, or ways of putting outfits together that I can pull into my own day-to-day getting dressed. This can be as simple as coming back to your screenshots a week later and editing.

3. Take inventory of what you have (and try things on!) Major honesty moment here in that I haven’t yet really fully done this - mostly because the weather has still be warm, and so I’ve delayed the task of bringing out items stored away from last winter and swapping them with my summer things. That said, I keep MOST cool weather items in my closet all-year-round, and only store a few things. I’m summoning the time & energy to do my full closet switch (which actually does not require that much time or effort but still gotta find the motivation/energy to do it). If you already have a good handle on what you have/don’t have in your closet, then this may be a smaller step in the process. It’s all about making sure you know what you have so you don't put another pair of straight-leg dark-wash jeans on your shopping list when you already have 3 other pairs (absolutely 100% not speaking from experience under any circumstances!)

4. Create a wish-list/shopping list - I use the my notes app for this. I will look at my previous wishlist, carry anything over that I am still thinking about (I often have evergreen/wardrobe gap items on my wishlist — for example, I don’t have a black blazer (!?!?!), and I have been thinking about a solid gold charm necklace as a little treat since I birthed my second daughter accidentally sans epidural and she’s almost 4, ha!) and just add things as they come to me. Sometimes it is something very specific (a specific white tee-shirt, for example), other times it’s more broad - like a brown boot with a 1-2” heel.

5. Go about my life & buy a few things and tinker with said wishlist endlessly- As I make purchases, see new things, realize I want something else, I am always tinkering with the wishlist. I’ll add in notes about pieces I like or that catch my eye. I’ll note if I buy something and return it (I was looking for corduroys & returned a pair from Gap and a pair from J.Crew). I will remove things that end up being just a passing desire (I do this a lot - sometimes the act of just putting it on my wishlist and knowing I can come back and buy it if I actually do want it helps to quell the desire and move on). The more I get dressed in the season the more (or less) I might realize I want something — maybe it becomes extra apparent that there is a gap in my closet (every rainy day, for example, I ask myself why I haven’t bought a proper raincoat), or maybe I realize it’s really something I want or am lusting after but can totally live without.

This process is by no means perfect, but it is one that I can easily manage, and, in general, it serves me very well!

How do I implement it in real life?

The beginning of a new season always puts me in a shop-y mood. And, since, it’s fall (arguably the best season fashion-wise), the shop-y mood is usually extra shop-y. Fall is definitely my favorite season to dress for. But, it also marks the transition away from summer. Despite embracing the back-to-school vibes (and actually sending kids back-to-school), I still haven’t felt fully ready for fall. We’ve been hanging on to summer clothes - wearing shorts and t-shirts, dresses, sandals, and begrudgingly pulling sweatshirts or jackets on when we absolutely have to.

I simply cannot force the season change. A thing about fashion is that it’s always looking forward (by several seasons), and while it’s inspiring and fun and exciting to look at, when it comes to thinking about your day-to-day and how you’re actually getting dressed, it can be quite frustrating for all that inspiration to feel so far off from your real life (not to mention at a price point that is much more than two seasons away, HA!)

BUT. The mornings are chillier. The leaves are changing colors and falling (adds rake leaves to the ‘to do’ list. We’ve been apple picking…twice. We decorated our front yard for Halloween. And I’ve been reaching into my sweater drawers more and more frequently. So yes, fall is here. And, we’re excited about it! It really is a beautiful time of year, especially in New England, and, of course, the clothes, the clothes are *chefs kiss.*

So, I’m finally ready to lean into the new season, and I’ve make a couple purchases here and there that I have been putting to good use. I’ve collected my inspiration, done lots of review and browsing, and I even have a wishlist of my own.

There is a timeless aspect to so many of the best fall outfits and pieces (this year, pieces like structured blazers, trench coats, and tailored trousers are really feeding that timeless vibe). While I can get overwhelmed with the number of pieces I see and love each fall season, I rarely get that feeling of, “I need to throw everything away, burn it all down and start from scratch.” Instead, I get excited about the chance to wear things that have been sitting patiently in their drawers, or on their shelves, or maybe even packed up in seasonal storage in my basement for awhile. I get inspired by new ways to wear those things, or new ways to put outfits together. Or to repeat outfits from past seasons that I have loved. And, of course, I get excited to buy a few new things.

I LIVE for jeans and a sweater season. Sweater / Tee / Belt / Jeans / Shoes / Bag / Sunnies

My fall wardrobe is weighted with items on which I have spent more money, and therefore thought about more carefully, and ultimately, tend to appreciate much more and for much longer than other pieces in my closet (looking at you hangers of dresses I’ve bought impulsively in the past) - that may have filled their one-time-wear destination, but don’t necessarily fit other requirements of my closet. Not rocket science here, but a good reminder that taking just a little bit of time to think about new pieces (and it doesn’t mean you have to be spending $$$, it can be for any dollar amount)— how am I going to wear this? Am I going to wear this in my everyday life? (Following these tips is a good place to start!)

Browse these images & find all sources on Zeen

So, what’s the inspiration this year? It’s classic, it’s “effortless” (although we all know looking effortless takes effort!), it’s elegant & sophisticated, it’s functional, it’s a little preppy but has modern touches, and it’s popping with vintage vibes.

What I love about the visual inspiration I’ve gathered, is that it’s about the full look, not the piece. Which, I get, can be extremely annoying — sometimes you really just want to know where that specific pair of jeans that look so great and are the perfect wash are from (they are probably from somewhere in Europe that doesn’t ship to the US, sob). BUT, it’s also really important because at the end of the day (or, in most cases, at the beginning of the day, please don’t judge me for this joke), we’re getting fully dressed and not just putting on a single piece. That pair of jeans doesn’t do you much good if you don’t know what shoes, shirt & coat you’re going to pair them with!

So, let’s unpack a bit. You can find all items linked in collages & the text in my Fall 2024 edit on Shopmy.

Slingback Heels / Brown Cardigan / Snakeskin boots / Straight leg jeans / Wide-leg jeans / Suede Jacket / Handbag / Corduroys / Silk Pants / Blue Cardigan / Knit Tee / Cableknit Cardigan / Suede Flats

Texture in every outfit: These outfits are SIMPLE - but make jeans and a long sleeve or sweater pop with a suede or corduroy jacket (or piece). Wear animal prints as a neutral, and add a pop of color (I’m deeply obsessed with these heels). Wools, and patterns and interesting fabrics in all different kinds of color. Standout pieces include: These corduroy pants are amazing. Deeply enamored with these cheetah-print silk pants. Suede bag goals.

Effortless Chic / Sophistication: We all know that it takes effort to look effortless, but this season, I’m so inspired by relaxed silhouettes (saying goodbye to ultra tight styles with a giant sigh of relief!), layering sweaters over shirts, scarves paired with coats - everything is functional, but also beautifully composed. Also, lots of tonal looks - something about all the same color or shade of similar colors is key to getting that sophisticated, effortless look. Standout pieces include: A delicious, crew-neck, cozy sweater with a thick collar & cuffs that is perfect for wearing and draping - Tuckernuck makes one, I’m dedicated to my La Ligne. Creamy silky pants (look for less here) to wear with a tonal sweater. A great scarf that goes with everything.

Vintage Influences - It’s a “only the hits” type of situation — with the best of the 70s (high rise flare pants I love you so much), saddle bags, vintage jackets that are way better than the new version, and beautifully cut blazers. Standout pieces include: Don’t sleep on etsy - I’m serious. I love these jeans, and would wear them with sneakers, ballet flats, boots, a kitten heel.

Fringe Leather Skirt / Black Mule / Earrings / Belted Coat / Black Waistcoast / White Button Down / Navy Jacket / Grey Sweater Vest / Veronica Beard Handbag / Savette Handbag / Bow / Polo Sweater / Turquoise Necklace / Western-style short Boots / Denim Shirt / Tall Boots

Western-Inspired - Last fall brought Western inspired details to the forefront and it is still riding strong. I freaking LOVE western touches, and reach for my beloved cowboy boots that my husband bought me for my birthday when we first started dating every chance I get. I’m inspired by head-to-toe denim, especially with special detailing and stitching (also a bit of a nod to the 90s), cowboy-inspired boots and denim jackets. Standout pieces: I’ve been living in this jacket, and I love this similar one too. I’ve admired these boots for a long time, and might bite the bullet this year. These are similar at a lower price point. The buckles on these ballet flats!!!

Tiny Feminine/Girly Details - Balancing out the tendency towards tailored, but not tight styles are bows, tiny belts that cinch your waist when everything else is a little more voluminous, Mary Jane’s, scarves, beads, bags with top handles, kitten heels and sexy ballet flats. Standout pieces: I’m obsessed with these ballet flats, but they’re not in my budget. These have been doing the trick - the v-shaped toe is SO GOOD! I’d like to see these restocked! This is a really nice thin, but not too thin belt. And this bag will take you far.

Preppy Meets Modern - That perfect combination of botton-downs, loafers, and structured coats and jackets, plus perfectly tailored trousers. Standout pieces: A great button down - I want to try this one. A crisp polo shirt as a layering piece. Polo-style sweaters.

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I hope this gets you thinking about how and energized to style things you already have, dust out anything that’s been sitting in your closet for the summer, feel energized about getting dressed, and maybe get excited to think about and plan for a new item or two (or three!)

I would love to hear (sound off in the comments) - what is inspiring you to get dressed right now? Do any of these images or ideas resonate for you? Have I missed anything?

I am excited to share more of the things that I am wearing day-to-day, so you can see a little of how I’m pulling this inspiration through IRL.

As always, thank you so much for being here!

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