I believe that it is worth investing in maternity jeans early on in your pregnancy - they are so much more comfortable on your expanding waist, even with a small bump so why wait? Also compared to normal jeans they will have limited wear (although I have friends who still wear theirs for a Sunday roast). You will most probably be wearing them for a while once the baby has arrived too - so get some you love.

There are many options in maternity shirts from Old Navy. There are tanks for layering, nursing, or for use when the weather is warm. There are also long sleeve and short sleeve maternity T-shirts in many stylish colors and patterns. For those looking for a special occasion outfit, or something that can be worn to work, there are also tops that can be worn with dress pants or skirts.

The advantages of under the bump are that they aren't so bulky under tops and to combat exposure or to allow you to wear a shorter top you can always wear a belly band or long vest top under your top top. Under the bump tend to work better for skinny, stretchy style jeans as the stretch in the denim will hold the jeans on your leg as supposed to having to rely on the waist band only.
During my first trimester, I thought I might get away with continuing to wear my low-slung hipster jeans for the duration. And I probably could have eeked them out for way longer than I did, had I invested in button extenders or a Bump Bandeau (as recommended by JTryner in an earlier thread). But there was always going to come a point when I got a little larger all over (be it from swelling, fat or, y'know, the extra 2 ½ pints of blood that swishes around in women when they're growing a foetus).
As of September, 2017, Destination Maternity operates over 1,000 retail locations in North America, including 512 stores, predominantly under the trade-names Motherhood Maternity®, A Pea in the Pod®, and Destination Maternity®, and sells on the web through DestinationMaternity.com, Motherhood.com and APeainthePod.com; Destination Maternity brands are offered at retailers such as Macy's and Boscov’s.

Thyme Maternity is by far one of the best retail jobs I've ever had. Full time employees have great benefits and the management was always very positive and encouraging. The discounts were amazing and helping pregnant women find clothes and products that made them feel comfortable and pretty was a fulfilling and fun experience. The breaks were often and fair and the shifts were always a reasonable length. My only complaint is that the part-time hours could be unreliable but for a student or someone with a financial plan to fall back on it would be perfect. I would absolutely recommend working for any of Reitman's affiliates if you get the chance!
I'd say so.  I just loaded up on a bunch at the outlet in Vegas and normally wear size 6-8 depending on the brand, and most of the size small fits me fine.  They carry some different jean brands though, and sometimes I'm a medium in those, but that's normal for jeans to fit weird like they do when we're not pregnant!  Don't even escape that when looking for mat clothes!
I worked for Reitman's for over 9 years, moving to all branches, eventually being moved to thyme because they said it was the only store I would be able to advance in. After working there for a year and a half I was told that they were just going to hire from the outside instead because it wasn't fair that I might play favorites. While I enjoyed the time spent there with the people I worked with it wasn't a career sadly.
A changing wardrobe is one of the inevitable side effects of a changing body and you might end up wearing comfy maternity clothes long after you start breastfeeding. Throughout your pregnancy, you’ll want to find comfortable clothing that accommodates your growing bump, but shopping for maternity fashion doesn’t mean you have to completely forgo your style goals.
I worked there a few years ago and the discount and hours were great but the management at the time was not the best. They were condescending when I made a mistake and they were very stingy about useless things in the store. Other than that, it is interesting to learn about the special material they use for the clothing and different products that help with during pregnancy (e.g. body creams and bras) and after pregnancy (e.g. nursing shirts).
Pros: 1) The staff were very helpful and friendly and welcoming to us and our beloved small dog. 2) Very reasonable prices -- which seems unusual in maternity fashion retail. 3) While my wife and I did not love any of the designs available in the store (she was looking for a relatively formal dress for her baby shower), there was one we quite liked, and they had a much greater selection of casual ware. 4) My wife tells me there were huge, well designed change rooms. There was a nice place for me (and other men) to sit so I could do my yelping while my wife tried on clothes. Cons: 1) There were some ads on the wall with models wearing especially nice maternity clothes, but the particular style we liked the best was no longer available to purchase. I prefer the practice of many other chain retailers of advertising particular styles that are actually available to buy. 2) Not so good (although perhaps understandable) return policy. Everything on sale is no return and the one dress we liked just enough to buy, we learned at checkout was no return also (even though it was not on sale) because it was classified as an "occasional" or "party" dress. My wife was on the fence about the purchase anyway and this was enough to make her change her mind and not buy it.
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