Forum member Star recently posted about an interesting wardrobe editing question that she found on the blog, Full Life Reflections. When you’re unsure whether to keep or pass on a wardrobe item, ask yourself this question: “would I buy it now?”

If the answer is no, ask yourself why? If you’ve come up with compelling reasons that are no longer aligned with short and long-term style goals, pass it on, or pop it into a holding zone away from your other wardrobe items just in case you change your mind. If the answer is yes, hold onto the item a little longer. Like forum member Star, you might find this closet editing question more logical and easier to answer than, “does it spark joy?”

Personally, I find it useful to ask myself whether an item sparks joy when it’s on the closet editing chopping block. I usually have a definitive feeling one way or the other, and follow my emotions. I also really like “would I buy it now?” because it prompts reflection that is less emotional, and more logical. This will give you more information for wardrobe planning and lay the groundwork for further reflections about the evolution of your style.

You do need to be careful when asking this question if you are prone to over-editing your wardrobe, or if you are a particularly moody dresser. For example, an item you wouldn’t buy right now might fall back into favour relatively soon and gain a new lease of life. You don’t want to wish you had a great red jacket, only to realize that you passed on a fabulous one a few seasons ago because you weren’t in the mood for red.

I recently passed on two old Smythe blazers because I hadn’t worn them for years. One was twelve years old, and the other seven. Both were a shade of grey, very structured, and no longer sparked joy. I had held onto them because equestrian looks are close to my heart.

Asking “would I buy them now” just reinforced my decision. They were grey, which I don’t enjoy wearing. Their stiff, structured silhouettes aren’t a great fit for my active lifestyle. Instead, I was reaching for much more comfortable, playful and colourful Boden and Hobbs blazers.

A simple question can surface thoughts and emotions that make it easier to decide whether to keep an item or not. These two questions are complementary. “Does it spark joy?” for the heart, and “would I buy it now?” for the head. 

Over to you. What do you ask yourself when you’re evaluating an item in your wardrobe?

Washington DC-based Alicia Tenise Chew is a fashion, lifestyle and travel blogger who documents her outfits on her website, and on Instagram. She is a confident dresser with a relaxed and very polished boho-lite style. Alicia is a dress gal at heart who loves hats and colour, and wears patterns with pizzazz.

This boho white midi dress has relaxed Summer vibes written all over it. The tiered A-line silhouette and loose fit are breezy for hot days. The gathered bodice and tiers create visual interest while the elbow-length puffed sleeves bring volume and drama. Alicia adds subtle pattern to the look with her casual espadrille wedge sandals in a cheetah print. Her oversized sunnies with tortoiseshell rim give the effect of a second animal print pattern. Our blogger’s wavy locks fit the beachy Summer feel perfectly.

Alicia loves a good conversational print, and this colourful safari one would make me smile if I saw her walking down the street. It graces an above-the-knee A-line popover dress with empire waist that creates structure. Her dainty strappy sandals have pyramid stud accents in silver metallic that add dressy bling to the look. Our blogger mixes metals with oversized gold-toned hoop earrings and an on-trend initial necklace. A mini straw handbag and red lipstick complete the look.

Sporting a dress unbuttoned as a topper is a clever way to get more wear out of your clothes. Here, Alicia is wearing a short-sleeved maxi dress as a duster layered over a fun graphic tee and cropped kick flare jeans. Tucking the tee lengthens the leg line from the hips up. The graphic print has some yellow in it which is a great match with the orange-yellow leopard print topper. White leather sneakers add crispness, and match the white tee, while Alicia’s small black bag echoes the leopard spots. Bright lippy and our blogger’s trademark radiant smile are the fab finishing touches.

Alicia is a vision in this bright multi-hued Summer maxi frock. The fitted smocked bodice provides structure, while the tiered A-line skirt adds breezy maximal flair. Our blogger’s studded flat sandals peeking out from under the colour-blocked dress bring subtle shine to the look. Her oversized tortoiseshell sunglasses and sleek long locks add lots of visual and textural interest. A small straw bag with top handle is the perfect accompaniment to this vivacious Summer outfit.

This is a fab example of Angie’s Dresses with Tall Boots outfit formula. Alicia is sporting a fit-and-flare mini dress in gorgeous shades of pink and red. The fitted waist creates structure, while the billowing sleeves add playful drama. Tall tan boots add buckletloads of ’70s glam to this early Fall boho look. The shorter hemline is great for Team Legs and showcases the boots, making them as much of a focal point as the dress. Alicia finishes off the look with raspberry lipstick and a Panama hat in stone that bookends her suede boots.

The clever design of this sweater dress with its horizontal ribbing up top and vertical ribbing for the bottom part makes it look like a two-piece dress. This creates vertical integrity by drawing the eye up and down. The knit fabric casualizes the look and gives it a boho feel while the gorgeously eye-catching bright yellow makes it a veritable showstopper. The taupe suede pointy-toe booties with sturdy block heel, and Alicia’s wavy ombré locks continue that boho vibe. A cheerful floral face mask perfectly matches the outfit.

I can’t wait to hear what you think of Alicia’s fun boho-lite style. Let us know in the comments, and be sure to check out the rest of her fab outfits on her website and Instagram account.

This week’s roundup of top picks ranges from lounging comfies and simple breezy dresses, to fancy flip-flops and fun earrings. Be sure to browse all the colour and size options. If you catch items on flash sales, so much the better, although some items are already discounted. 

1. Midnight Bakery Tie-Dye Lounge and Sleepwear

I wear loungewear first thing in the early morning before I shower, and in the evening as I wind down for the day. I find the change of dress quite therapeutic and it’s very much part of my daily dressing routine. For bottoms, I like to wear floppy and very soft full-length wide legs instead of joggers, leggings, flannel pyjama pants, or shorts. These are not easy to find in the right weight, length, fabric and pattern, so I’m thrilled when I do find them. The wide peach tie-dye lounge pants from Midnight Bakery fit the bill and are sublime. They are breezier than they look, and I adore them. They are super soft, drapey, flattering, very comfy, and not too high in the rise. Size up if you want a looser fit. I’ve ordered the hoodie to match. There are joggers and camisoles if you prefer those silhouettes.

2. Unity In Diversity

This is a Canadian footwear brand that is manufactured in Europe. For example, these fun, high-energy flat oxfords are made in Portugal. They have rubber soles for good traction. Extremely well-made and comfortable. Fits a wider foot. The cushioning foot bed is removable if you need to insert orthotics. Check out the rest of the brand for very comfortable and uniquely designed maximal footwear. There are lots of interesting design details, and great patterns.

3. Old Navy and Gap Casual Summer Dresses

Don’t underestimate how great a simple and comfy Summer dress from the Gap or Old Navy can be. Every year, my clients find one or many from this retail source so keep them on your radar. They usually launder well, are adequate to good quality, and can work as a swimsuit cover-up. The Gap’s dresses tend to run big so size down. Prices are affordable.

4. Talbots Flounce Skirts

Talbots does a lovely selection of cotton-rich, flouncy midi and maxi skirts every Summer season, and this style caught my eye. They are well-made, substantial yet breezy, streamlined yet fluid, easy to launder, and fit a curvier bottom half extremely well. Size down if you’re straighter through the hips, seat and thighs. Available in petite, straight, and plus sizes.

5. B New York Conscious Pleat Sleeve Button Down

This is a gorgeous architectural shirt, which has been produced sustainably and ethically. Great drape, good fabric, and fun sleeve ruching detail. It’s voluminous but with structure in the right places to temper the volume. The narrow forearm fit, shorter front, and side slits create subtle structure. I tried it but needed a size down which they don’t offer. I loved it. It would have been mine in the right size.

6. Flip-flops with Arch Support

For some, flip-flops spell Summer. If you’re after a pair with arch support, try out brands like FitFlop, Vionic, Birkenstock, Clarks, Dansko, Merrell, Mephisto, Reef and Sanuk. FitFlops, Birkenstocks, Vionic and Sanuks are favorites with my clientele. Here’s a selection of winners, and some brands offer wide sizes.

7. Ann Taylor Earrings

If you bat for Team Earrings, Ann Taylor has some fun and unique pairs at the moment. Playful and on-trend, yet classic and refined. If I wore earrings, I’d wear the pretty pearl daisies.

You might have more than one of exactly the same wardrobe basic in rotation. For example, I have four of the same beige bras, six of the same beige camisoles, and eight of the same beige knickers to match. I also have two pairs of exactly the same floppy lounge pants, two of the same navy nighties, and many pairs of the same nude-for-me knee-highs.

I’ve also found it useful to have two of exactly the same quiet and simple wardrobe essential in rotation to prevent laundry bottlenecks. For example, I have two of the same of these pairs of jeans and white cotton pullovers. I used to have a few of same white button-down shirts too. The extra is not a spare, but simply another top and bottom in my wardrobe.

I could have bought a different pair of blue jeans and white cotton pullover to cover my needs and add variation. But to keep things very simple, I bought exactly the same because they are versatile workhorses. Does anyone else have more than one of exactly the same item in rotation?