Building on the earlier suggestion, I definitely think jumping in on Friday is the move. A few years back I tried waiting for Cyber Monday to save a few bucks on a heavy parka, but by 9 AM my size was totally ghosted. Now I just shop the Friday sales and I'm honestly much more satisfied with the selection. I managed to snag a The North Face McMurdo Parka NF0A33RF and its been a beast for those freezing commutes. Here's what works well for me:

• Grab merino base layers first since they sell out fast.
• Look for 600+ fill power for New England winters.
• Focus on technical shells that dont usually stay in stock. I picked up some Smartwool Men's Classic Thermal Merino Base Layer gear last year and it keeps me so toasty. Tbh, the peace of mind knowing you have your gear before the first storm hits is worth more than a tiny Monday discount.

^ This. Also, unfortunately 300 bucks doesnt go as far as it used to for Boston winters. Big brands keep hiking prices while quality drops, which is honestly disappointing. I usually hit the Friday sales early for the best value before sizes go. Some budget-friendly gear:

• Dickies Mens Sanded Duck Insulated Hooded Jacket
• Kamik Mens NationPlus Insulated Winter Boots Cyber Monday is basically just leftovers now, ngl.

I'd go with Black Friday if I were you. Waiting until Cyber Monday for clothes is risky because the inventory gets wiped out so fast. If you're looking for winter gear in Boston, you need reliable stuff and you need it to fit, so dont gamble on the leftovers.

• Stock levels are way better on Friday. By the time Monday rolls around, you're usually looking at XS or XXL leftovers in the clearance section.
• The price difference is usually negligible, like maybe 5% or 10% tops. Not worth the risk of losing your size imo.
• In-store options on Friday let you actually check the insulation quality which is huge for surviving a real cold snap. For a $300 budget, you should look for these specific items:
• Carhartt Loose Fit Firm Duck Insulated Flannel-Lined Active Jacket which is basically a tank for New England wind.
• Columbia Men's Bugaboo II Fleece Interchange Winter Jacket is a solid 3-in-1 that stays under budget.
• Sorel Men's Caribou Waterproof Winter Boot for dealing with the heavy slush. Tbh, its just safer to buy early. I've tried waiting for the Monday deals before and ended up having to pay full price for a different brand because the sale items were totally gone. Just grab your stuff on Friday morning and call it a day.