After confessing to you last week that I’m going through a frumpy phase, I’ve become more obsessed with boots than boobs in my attempt to remedy my shoe situation. I’ve wasted hours looking for the perfect pair (scroll to the end of today’s post to see my favorites) because I’m caught up in the myth that a single item of clothing is the answer to all my problems. Fortunately, reader comments to last week’s post have broadened my perspective, and I want to try pendants, patterned tights, stacked bracelets and grouped brooches–just as soon as I have the right shoes.

High quality boots, like winter coats, are a big ticket item for me. They should last for years, which makes spending $300-$500 on them justified. However, preparing to spend that much money on a single item also makes me giddy–like I’ve just stepped into a department store with a gift card and can choose to get something I need or something I love. If I didn’t have to be so practical and could purchase anything I wanted from big bust friendly stores this season, here are the top two items I would choose.

Perfectionist Dress in Stretch Silk Satin from Saint Bustier

Saint Bustier Perfectionist Dress

I love the lines, the draping, the sheen and the seams of this dress that fits up to a G cup. If I worked in an office during the day and had holiday parties ahead of me in the evenings, I could completely justify spending $275 on it. Lately Saint Bustier has seemed overrun with form-fitting Miranda, Nigella and Paloma dresses and a large contingent of knot-ties and wraps. However, there are a few original options sprinkled in the mix that make it worth visiting again. Do you have any favorites from their current offerings? If so, I’d love for you to share links to them in the comments.

Quilted Leather Jacket from Pepperberry

Pepperberry black leather jacket

Based on the early positive reviews by three customers who wear super curvy, I have a feeling this is a jacket that I’m really going to regret not finding the funds for. Three years ago, Tina wrote about the challenges of finding a bust-friendly leather jacket, especially in a timeless style with a little edge from Pepperberry (I’m sorry that most of the photos in the linked post have been deleted, but Tina’s Pepperberry example at the bottom remains). If this year’s jacket zips over the boobs without flattening the quilting at the bust line, then it’s as good as a new pair of boots.

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Speaking of boots, here are the two pairs I’ve fallen in love with.

John Fluevog Sherry Boots

fluevog boots

Ultimately, I decided I need something a little less memorable since I’ll be wearing the same pair over and over again. But even hidden beneath pants, these boots looked amazing.

fluevog boots with pants

Zarah Boots from Apia and AutoGrafNewYork

This pair has the “classic with a twist” look that I’m looking for, and the size 39 that I found at Eneslow were the last available pair in that size in the United States. Not only are these handcrafted Italian boots amazing, but so is the story of the designer behind them.

Apia Zarah Stretch Leather Boots

I was so disappointed to discover that I need a slightly wider toe box than these offer!