5 Questions to Ask Yourself when Shopping for a New Season

One of the most exciting things about entering into a fresh new season for me is curating my personal style to fit. Now, this isn't to say that immediately once the calendar shifts I sprint to the nearest store and spend my savings on new, trendy clothes. It is quite the opposite, actually. Even before I started blogging and styling, I liked to enter into a new season with a well-thought-out plan. 

When I know I'll have a day free of distraction, I like to spend time going through my closet and drawers and making 4 separate piles: keeping (transition or staple pieces), donating, selling (I love Poshmark and local consignment shops), and storage (clear plastic bins are the way to go). Although it doesn't take me more than a few hours, I like to schedule out the whole day so I can take my time and enjoy the process. I light some candles around the house, put on a pot of tea, and turn up a good playlist (my favorite on Spotify right now is The Everygirl Listens: Fall).

Once I'm finished curating what I already have on hand, I spend the rest of the day reflecting and doing my research - aka browsing fashion blogs, my favorite shop's new arrivals, and Instagram/Pinterest. Another thing I've gotten in the habit of doing before I begin shopping is asking myself 5 questions. I wanted to share these with you babes today in the hopes that they will help you feel inspired, motivated, and confident when heading into a new season. 

1. What did I wear most last year during this season? 

Did I wear a ton of over-the-knee-boots, or did I opt for comfy loafers? Did that bag that I needed just sit at the top of my closet all season? For me, I look at the items I bought that are still in boxes (hi, glittery platform heels I wore once in New York), or clothes with tags still dangling around in my closet. Sometimes I make the mistake of buying items that I think I should wear, rather than what I enjoy wearing or feel comfortable wearing.

Alternatively, was there a piece in particular that you couldn't get enough of last year during this season? For me, I grabbed my wool beret more often than I ran to Starbucks for a PSL (so... a lot), and I wished I had bought the same design in more colors than just cream. This year, after reflecting on these 5 questions and realizing that, the first thing I ordered was a blush wool beret because I know I will be wearing it a ton. 

I feel like I learn the most from reflecting on this question in particular each season, and I find it really useful when shopping for new pieces so I don't make the same mistakes. 

2. What do I have in my closet that can be used as a transition piece?

Think of the pieces you wear year-round; pieces that you consider a "classic" and can transition with you from season to season. If you start with something like a nude bodycon dress, you can easily add a leopard scarf and nude heels, or a furry jacket and booties. When I curate my closet at the end of each season, I store the obvious non-essentials away in bins in our basement so my closet isn't super cluttered. It makes it much easier for me to grab what I need in the morning for work or in the evening for an event without shoving past clothes I can't possibly wear (like chunky, knit scarves in the Summer, or sun hats in the Winter).

The items that I keep on hand year-round are light, neutral scarves, fedora hats, jean jackets, little black/white/nude dresses, pointed toe heels, loafers, booties, etc. These are pieces that you can add layers to if necessary, or dress up/down depending on the season. It is useful to know what you already have and love so you can purchase new items that compliment or pair well with them. That way you're not starting from scratch and spending a ton of money when styling new outfits.   

3. What is my budget?

Set aside a little time to think about your budget realistically. Your budget can be $20 or $200, it's not a number that you need to share with anyone, it's simply something you should feel comfortable with. Nothing is worse than being at a store and finding the perfect piece for your wardrobe and then having a 20-minute internal debate in the dressing room about whether or not you should/can spend the money. If you prefer to bargain shop, and get a personal high from finding deals for $5 on the sale rack at your local consignment store, then planning an afternoon outing to Nordstrom is probably going to be frustrating and a waste of your time. 

Know before you go so that you can manage expectations, pick out items within your budget, and have a shopping experience that doesn't leave you feeling deflated or regretful.

4. Which area of my wardrobe is lacking most? Office wear, date night outfits, casual/comfy pieces?

You know those days when you're like, "but I have nothing to wear!", and you go around stomping in your room and scaring the shit out of your husband 15 minutes after you were supposed to leave the house? No? Me either... But really, when do you find that you're most frustrated when getting ready? Is it when you're getting dressed for work/ going out with friends/ heading to the gym/ just want something to run errands in?

For me, I get most frustrated in the mornings when I'm getting dressed for the office. I don't particularly love office wear and I haven't found that sweet spot yet of feeling super inspired or creative with it. If I'm being honest, I'd totally rather be in a cute mini dress or old jeans and mules. Realistically, I get dressed in office wear 5 out of 7 days every week, so I know that this is my main focus when shopping for this season.

While writing this post, I decided to follow my own advice and evaluate my current wardrobe in regards to "office appropriate" clothing, shoes, and accessories. To no surprise, I only had 2 pairs of shoes that I actually enjoyed and felt comfortable going to the office in. I decided to set my budget and ended up finding 3 new, practical pairs of shoes that I am SO excited to style (1 pair of patterned mules, 1 classic kitten heel, and 1 patterned pointed toe heel). I got 2 of the shoes from Target for under $30 each (linked below), and the 3rd pair of shoes from my favorite local consignment shop for less than $20. Even though it seems like adding shoes to my wardrobe is such a trivial thing, I know that it is going to drastically improve the way I get ready in the morning, and how I feel heading into the office. 

5. What events/holiday parties are on my schedule for this season? 

This is helpful to think about pre-shopping so you can plan ahead for the events and parties that you already know about, or are an annual expected-attendance kind of deal. Before you blow your whole budget on one pair of over-the-knee-boots or a blue tufted backpack, you need to know if you're going to want a new fancy dress for yours and your hubby's office parties, or if you want to spend a little more than usual on your NYE outfit. This way you can set a little cash aside for those "special event" items so you're not stressing about it when the time comes to shop.

Or, you can add those events to your shopping list now (this is what I do throughout the year), so that you always have it at the back of your mind when shopping. If you see something that would work perfectly, you can grab it rather than waiting until the last minute. P.S. I just snagged a pink satin gown for NYE for less than $30 on Poshmark (*cue happy dance)!

Jade Nikkole Photography

Shop my favorite Fall finds:

Are you embracing the new season yet? Have you asked yourself these 5 questions? Comment on the last photo on my Instagram feed and tell me, or tag me in your favorite Fall style or OOTD!

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xo Anna Elizabeth