Some tips I've picked up along the way:
1. Regular size clothing only works for so long.
Your belly will soon outgrow the rest of you, meaning that you either have clothing that fits everywhere but the bump, or fits the bump but is too big in the arms, shoulders, and hips. Jerseys and other stretch materials will help make clothes last a bit longer in your closet, but sizing up isn't always a great option beyond a certain point.
2. Comfort is key.
In the early months, you can still fit into your regular clothing, but the waist line is getting tighter and tighter. You may also want to hide the first signs of a bump because it tends to look more like a beer belly than a beautiful baby. For these first few months (and even now), I opted for skinny jeans or leggings with a looser top. Skinny jeans and leggings tend to have stretch in them, which makes them more comfortable all day long. A looser top will cover rigged pants closures or maternity panels, and accommodate the growing belly. Layer on a jacket or scarf and wear your heels while you can. I love these looks from Net-a-Porter, which exemplify stylish comfort.
Left to right: Zara's Strappy Sandals, Jewel Vamp, Basic Sandal, Ballerina Metal Cap Toe, and Pointed Ballerinas with Bow.
3. Shapeless garments won't do you any favors.
Just because you want to be comfortable, doesn't mean you should always opt for a-line dresses and flowy tops. In the beginning, before you start to really show, these garments work pretty well. After the bump pops, shapeless pieces just tend to make you look large, not pregnant. This can be solved by a well place belt just below the bust line, or simply look for more figure hugging garments. You'll be proud to show off that belly. As you approach the end of the pregnancy, muumuus may look enticing, but just... no. Don't go there. At least not outside of the house.
Maternity line Isabella Oliver makes some really cut, bump hugging jersey dresses.
Left to right: Ruched Tank Dress, The Urban Ruched Dress, Print Ruched Tank, and Ruched T Shirt Dress.
They're mighty expensive, but could be frequently worn to work or out on the weekends (meaning: they're worth the investment). I love maternity dresses because they are chic, an easy outfit, and can be worn different ways depending on accessories. If you like these and can sew, check out Megan Neilson's maternity patterns:
They are pretty easy to make (I bought jersey from Mood) and work well throughout the pregnancy. I couldn't make it with out the ruched skirt and the wrap top. I was wearing the ruched skirt at 3 months and it is still a go-to piece. If you make the tops in the same fabric as the skirt, you can layer them for a dress-like look.
4. Maternity clothing tends to be sized large.
I've pretty much bought a size down from my pre-maternity size across the board. Sometimes even two sizes. Doesn't make shopping online any easier, but don't be afraid to go down. Old Navy definitely runs big, as does GAP and Target.
5. Shop sales and flash sites.
It is hard to find cheap maternity clothes. Clothes that you will literally only wear for a few months, tops. Finding stylish, cheap maternity clothes is even harder. Stores like Old Navy, GAP, and Target are great for basics (LOVE LOVE LOVE Old Navy's Smooth Panel Skinny Jeans), but for special pieces or trendier items, look to flash sites. Gilt Group is the best for maternity clothing (plus they have kids clothing, toys, gear, and decor). You'll find brands like Ingrid and Isabell, Japanese Weekend, NOM, and more. Only downside is that returns are often for store credit instead of a full refund. Pea in the Pod can have good sales, too. If you find something that you think you'll be able to wear frequently for a few months, by all means, make the investment.
I'd love to hear any maternity dressing tips you may have. Happy shopping!