What’s the younger generation obsessed with on eBay? We went to Tim Booth to find out. Tim’s a promising young man—a senior at FIT. You might have seen him working at Drake’s or Stubbs and Wootton. He grew up in Philadelphia and sold suits (yes people still wear them!) at the mainstay Boyds. Let’s bid, kids!

Rocky Mountain Featherbed Coats & Jackets 902498 GreenｘMulticolor 40, $222

With winter right around the corner I’m starting to think about outerwear. This Rocky Mountain vest is really interesting with Donegal fleck and leather trim it almost makes me feel like I’m in Big Sky country and not the city!

1980's MEMPHIS Shohei Mihara for Wakita Wall Clock Pop Art Modern Japan Vintage, $275

I love the simplicity of this Wakita wall clock. I like to hang a lot on my walls and a bold white clock with such subtle accents might actually pop in comparison to everything else. I don’t take interior design too seriously, but it’s nice to have something thoughtful hanging up there.

Vtg DENIM & SUPPLY RALPH LAUREN USA FLAG Patchwork Mens Shirt sz M Military 107, $150

I’m a recent to two elements within this shirt: paisley and patchwork. Yes there’s a lot going here, but with so many traditional button downs in my collection it’s nice to try something new.

Postcard Chestnut Hill Academy Main Building + Gym Chestnut Hill PA, $15

Originally an inn and then a boarding school for boys, I graduated from the school in its third iteration as Springside Chestnut Hill Academy. A beautiful inn and gymnasium is a nice addition to any apartment!

Vintage Dartmouth Sportswear Collegiate Cardigan Size M Wool Logo Crest- Lined, $50

I had a stint in high school where I tried emulating one of my uncles who was always in a cardigan, but then I grew tired of them. This one, however, is great. The fact that it looks to be from the Dartmouth college shop makes it that much better.

Mens BARBOUR Border WAXED Jacket Green Size 38, $128

You can’t go wrong with a Barbour—they make you look forward to miserable weather. I’m always looking for an excuse to add another to the collection, and this has a bit more length (which covers tailored jackets) and fits the bill.

LL Bean Leather Tote Bag. Large with Multiple Compartments and Zippered Closure, $100

You can never have too many tote bags. I’ve never owned a leather tote and have been on the hunt for one. The printed liner makes this a bit more playful.

Vintage Levis 646 Orange Tag Denim Jeans Size 32 Tab, $80

Some things make no sense but you just have to have them. Flares are that thing. I’ve conjured up this twisted image of myself wearing a pair of old Tretorn’s, these flared jeans, an OCBD, a tweed jacket and topped off with a Barbour. Will I have the audacity to ever leave the house in them? We’ll see!

THE WATCH LIST is a regular series where friends reveal their auction obsessions.