This list isn’t for the ones standing on the corners, this is for the donations you drop off at your church or library or VA office or shelter.

If you attend an organized religious center, see if there is a homeless outreach program or a family or group in your church that has “adopted” a local homeless person. Gifts can be more targeted that way. Ask for an announcement to be made before services or placed in the bulletin.

While its tempting to go with the cheapest generic thing you can find, consider whether you would use the product yourself. Especially with women’s products.

This doesn’t mean it has to be fancy, suave is a good shampoo, secret or sure or any of those types are good antiperspirants. Consider buying unscented products if they’re the same price as the scented, some people are homeless because of sensory overload, surrounding ones self in a cacophany of artificial scents isn’t going to help. If buying a brand that doesn’t flake or rub off on your dark coloured work clothes is important to you, it is likely also to be important to the woman in the battered women’s shelter (or any other program).
For feminine supplies… Not every woman needs “super absorbency”, nor is every woman 5’10” and wearing a size XL. Even the cheap brands of pads come in thin varieties now, not only are they more comfortable to wear, they look better under clothes if a woman is trying to blend in with society to stay in school or stay employed (you wouldn’t want to be noticeably wearing depends under your clothes would you? Same concept.)

If you’re donating undergarments, remember women come in different sizes. If the dollar store has a buy 2 packs get 1 free, then buy three different sizes. The shelters open the packages and dole out only 1-2 pairs to each person so more sizing options will help more people sooner. Otherwise they have a box of size 10 undies sitting on the shelf and women who wear 6’s or 14’s going commando!

Here is the difficult part. Once a homeless person, especially a woman, has clothes, she needs to be able to clean them.
Laundry detergent! Colour safe bleach. Stain remover sticks. And more importantly, a token card at a local laundromat. I have some detergent now but no money to actually run the washer. Many laundromats now use cards instead of coins. You don’t have to worry about mis-use of funds, go to the laundromat, buy a card with $5 or $10 in machine credit and donate that (check with the place you’re donating as they may have other arrangements).

Really dressy clothes aren’t all that helpful. Any item that needs to be coordinated with something of the same style and/or colour are going to sit in a box for a long time. Donate nice basic supplies. Tops that are easily coordinated with multiple types of bottoms, jeans, skirts, under a sweater, etc. If donating a top or jacket for work, select something that will be able to suit the widest range of body types; extra wide necklines, lots of frilly lace, extreme tailoring, bold stripes, none of those are going to be very easy to pair with the limited hodgepodge of shelter donations.
If you’re at the local year-end sale of your favorite discount retailer and see something inexpensive that is just *so* cute, rethink and see if there might be something a bit less cute but more usable for more people.

There are also more and more mobile homeless now. That means the car has to be kept running. Inspections have to be done, the oil needs changed, and it has to be moved daily.
Check to see if you can buy a gift certificate to a local mechanic, maybe a chain like jiffy lube or equivalent, for an oil change or a tune-up or whatever.

I haven’t figured out gas cards yet… What I need most is gas money to get to my doctor appts. But… Again, most people that would donate to their local shelter aren’t going to know the people they’re donating for. I know that you can get gift cards but I don’t know how you would ensure it would be spent on gas rather than beer. If someone figures this one out please let me know!

Here’s some other ideas for smaller items that get overlooked…
Decent nail clippers or a small manicure set
Ointment for small cuts, something like neosporin (most stores have a store brand)
Advil, aspirin, allergy meds like benadryl or Claritin
Flashlights
Book lights (surprisingly perhaps, a lot of homeless people read)
A decent towel, consider a “bath sheet” or a larger towel. If you can sew a straight seam you can get terry cloth from a fabric store and make several large towels for the price of one fancy towel at the department store.
A small sewing kit. One with a decent selection of threads, a few needles, and some scissors. There’s no need for 20 different colours of thread or a thimble or measuring tape or threading tool, or all of that other stuff they like to put in there. Just 4-5 of the basic colours on medium size spools so there’s enough to hem a skirt or repair the hem on the donated top, etc.
Paper towels.
Wet wipes. These don’t need to be fancy, donate a Costco/Sams/etc box of the brand wipes, you’ll help 16 different people stay clean and keep their environment clean. try to avoid the alcohol ones if you can, those are hard on the skin (you wouldn’t want to wash your tender nether regions with alcohol would you?)
Batteries. Alarm clocks use batteries. School supplies use batteries.
Dental floss!
Non-alcoholic mouthwash
Battery powered toothbrushes (Colgate and oral-b both make inexpensive battery powered brushes that do a much better job than the $.45 soft bristle variety, those things are pretty worthless actually.)
If you donate socks, remember that not everyone wears men’s size 9-12.

That’s all I can think of for now, but that’s quite a lot.

If you have questions or suggestions of your own please comment!