Save. Spend. Splurge.

Ask Sherry: How would I spend $1500 USD on a shopping spree?

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Hi! If you had about $1,500 USD to spend on staple wardrobe items, what would they be? I have built up a decent wardrobe from budget items, but I think I am missing some classic investment pieces & have saved $$ for a shopping spree!



Voyeuristic spending.. oh my. 🙂

This is my list of essential pull-together items I’d buy and why.

I’ll give you my full list but not necessarily totting up to $1500 because I don’t know what you have / don’t like or want, etc.

I am listing also listing the full retail prices of them, but you can always buy them secondhand like I do (off eBay, Poshmark, etc), or wait for a great sale and then snap them up. Make your $1500 budget stretch!!!

Also, we’re just talking CLOTHES right? Not accessories? I may have to do another post if you come back telling me that included bags and shoes too 😛

Lastly, I live in Canada, so I have cool to cold weather most of the year, hence why a lot of my choices will be heavily focused on toppers and warmer items.


More versatile and not as harsh as black, I love, love, love, my dark grey suede leather jacket.

It goes with dark colours, it tones down light colours, it is more versatile than black, or brown (different shades of brown can be too cool or too warm and clash with an outfit). I’d give up all of my other leather jackets to keep this one.

The one I own above is discontinued from All Saints and this one for $450 is on the darkest side of grey (darker than mine, like a shadow grey), but the best match to the one I own above is this one from Tralsmin Tidle Suede Moto Jacket on sale now at $389 down from $1300.

If that is too pricey for you you can go for this gorgeous BlankNYC Valentine Leather Moto Jacket for $198.

Shopping options:


I snuggle up in this shawl sweater like you wouldn’t believe. I leave it open, I have it belted, it is a great topper to throw on top of any basic outfit.

This particular one seems to be a staple at Vince and I picked mine up for pretty $$$, but I wear it so often… here is a similar style they came out with this year, but in black.

Shopping options:


I like beige, or neutral shades such as greys of all kinds, or whites and ivories, because I don’t really love black.

The best colours to be neutral for me, is this shade of beige, white, ivory, or greys.

I got this cashmere sweater for $20 on a thrift store rack. It was originally a vintage J. Crew (I could tell by the cut and the quality), and I still love it.

Cashmere v-necks are always flawless pieces to wear over anything, and are true workhorses in a wardrobe. I think the cashmere game has changed to be able to hit all price points, but without a doubt, the more you pay, the nicer it will feel, and the less it will pill.

Shopping options:


Throw on a great, jewel-toned coat over anything and you look instantly polished. You could be wearing sweatpants and still look incredible.

The one I am wearing above is discontinued from Ted Baker called the Lorili wrap coat. They have since made other versions and colours, here is the same coat but in a deep emerald green.

This is assuming of course, you already have a great winter coat that will keep you warm. I love my Canada Goose Trillium for this and got one for my mother too.

Shopping options:


I have this exact dress in emerald green, indigo blue and plum pictured above. This dress is AMAZING.

Deep pockets for snacks or your phone, a great draped front that looks incredible and brings in a waist on any body, and it is a zipped up back sheath dress that is SO comfortable I am amazed. Hence why I have 3 of them.

The exact dress I am wearing in this shot is the Taylor in size US 6 from MM Lafleur (I would have fit into the US 4 but the waist was TINY, full MM Lafleur reviews here).

Shopping options:


Okay, I have two of these types of striped wrap tops. Both are discontinued. 🙁

I love stripes, but interesting wrap top stripes are really something I think looks great because you can wear it with skirts, or jeans, belt it, leave it unbelted.. it is so versatile and I wear these two tops heavily in my wardrobe.

The first one is from Derek Lam Crosby 3.0:

….and it was a striped blouse top in a size too large (US 6) that I bought anyway because it was only $25 (!!!!) down from $400, and I just cinch the waist tight with a great little cognac belt (also a wardrobe staple). Sort of similar (not really..) is this black and white striped one for $890, but you can find better options if you are patient and wait.

The second one pictured:

…is also a limited edition of a designer collaboration with Olivia Palermo and Chelsea28. I.. love this top. I took the belt and even made straps out of it so I could wear a bra with it. It looked like this originally but thin straps make my shoulders look huge, so I chopped the belt and made true straps out of it:

If you aren’t into stripes, any solid colour will do, but the key points are to look for a blouse that is INTERESTING. Interesting details, a wrap top, a bit of a bustier, something more than just a tank top or a t-shirt that is equally as comfortable.

With sleeves, without sleeves.. something cool!

The closest I have to these tops above is from Alton Gray Bustier Striped Poplin Top for $50 on sale.

Shopping options:


You knew this was coming right? I love dresses, and shirt dresses in particular are incredible pieces.

I like a crisp cotton in a white or a striped blue and white, and here are the two I would re-buy again in a heartbeat:

This first white one is from Theory:

I scored for $25 USD off Poshmark, as it had a few (unnoticeable) stains that dryvcleaning cannot remove. No one notices this because it is so faint (like tea stains), and the dress is so perfect that they just see the ensemble.

The second great striped shirtdress has that gorgeous knotted draping detail I love at the middle to bring in my waist, and I belt it (ALWAYS). I get lots of compliments on it too because it is so interesting, yet classic:

(See? That belt really makes the rounds, I wear it often and over everything).

Shopping options:


I LIVE in my dark rinse, high-rise premium denim jeans, specifically these Adriano Goldschmied (AG) Farrah High Rise jeans.

(By the way, short little booties are such a staple in my closet too. This pair in my photo above is the Brooklyn from Club Monaco but is discontinued. I love the Rag & Bone Margot Bootie but you should definitely size up at least a half a size)

Not everyone loves a high rise, it depends on your torso. To check what rise fits you the best, reach over and try to touch your toes. Where your body bends, is where your jeans rise should hit.

On me, it is right at my belly button, which means I need a 9″ or 10″ rise in my jeans.

They also have to hit you right at the ankle (get them hemmed like I do) and it looks so sleek with any pair of shoes – heels, flats, booties, whatever.

(Pointed ballet flats are also my favourite shoes to wear to look crisp and elegant, ballet toes that are rounded look a little more casual to my eye. This pair is secondhand and a discontinued model from eBay and from M. Gemi, but their loafers which are Stellatos are incredible classics).

Shopping Options:


I throw this flannel grey blazer that looks polished and crisp over my outfits and it elevates it instantly.

The fabric itself is a flannel grey, which is far more casual than actual suited wool blazer which I think would be too formal for everyday wear.

You can aim for other similar blazers in neutrals and in unusual cuts or fabrics so it doesn’t look too suit-y.

Shopping options:


I love wrap skirts because they drape nicely and look amazing, like the one in pure double-faced silk from MM Lafleur that is discontinued, called the Lenox skirt. They realized the price point of $495 USD was probably out of reach of most consumers so they still have the skirt, but in cheaper fabrics. I have this skirt in plum above, and also in a dark navy.

Those were all the colours they had, aside from black, and this skirt truly is phenomenal in its draping. It makes me feel comfortably covered up for the office yet sexy.

I love a great paperbag waist skirt, like the one shown below that I have belted (AGAIN! THAT BELT!):

This skirt came from Simons from a brand called Girls on Film. It has long since sold out and this is one of my all-time favourites. It has a front zipper that goes up assymmetrically, and if this skirt ever died, I’d have it remade from scratch by a tailor, it is so good.

My loves are wrap skirts, draped skirts, paperbag waists. It’s pretty simple.

(I would LOVE this Johanna Ortiz striped one but it is way pricey at $745…. too trendy for me at that price or this one from Gabriela Hearst that is just incredible but also too pricey at $875 )..

Shopping options:

Those would be my main picks, I’d say. Hope that helped! Maybe you could specify what your lifestyle is like, where you live (seasons and weather), and other such notes.

Still have a burning question?

You can ask any question using the form here and all of my previous Ask Sherry posts are here.


  • Susan Tan

    * I would buy ONE pair of handmade shoes with $1,500, most likely from Carmina or another bespoke shoe maker.
    * I would go on a treasure hunt high-end consignment stores and thrift clothing stores. I’m always on look out for gala gowns for gala events.

    • Sherry of Save. Spend. Splurge.

      You go to gala events!? How fancy. I own a few gowns and have been to none…

      • Susan Tan

        In San Francisco, there’s a lot of “relatively affordable” gala events like SF Opera Ball with the SF Bravo! young professionals Club and the SF Ballet Gala with the Encore! young professionals club where tickets start at $300 USD each. I also like to volunteer at local gala events in Bay Area which is a good excuse to wear a gown and get free admissions to a gala.

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